Affordable Stays Near Crescent Beach, Shelter Island

Just 1476 feet to the beach, this bed and breakfast is located in Shelter Island Heights. A free breakfast is served each morning. Cable TVs are provided in each room at Seven Resort Style Inn near Beach. Featuring a seating area, rooms also include a private bathroom with a hairdryer and free toiletries including sustainable amenities from Cold Spring Apothecary Natural French milled soaps from Pre de Provence. An on-site garden provides a perfect place for guests to relax at Seven Resort Style Inn near Beach. WiFi access and on-site parking are provided free of charge. Guests can also enjoy an on-site contemporary art gallery. Shelter Island Country Club is 1640 feet away. Perlman Music Program, Sylvester Manor and North Ferry are within 1.2 mi of the property. Mashomack Preserve is 2.9 mi away.

- "Peaceful, pampered , lovely." - "Amazing stay at Seven" - "Our stay at Seven was relaxing, refreshing and fun and we can't wait to return." - "Will absolutely be back!" - "This was a peaceful retreat." - "Excellent place, felt like home and luxury all at the same time." - "A Peaceful Getaway with Heartfelt Hospitality" - "A gem!" - "The Seven on shealtef lsland was the best R&B i ever stayed at." - "pretty place"

Lovely two bedroom sleeps 5 with huge deck and endless waterfront views. Fresh paint all new linens choice of two private community beaches one within a one min walk. Dock, boat and trailer parking at the house, cement boat ramp walking distance. Lots of great fishing fluke, flounder, striped bass weakfish, bluefish, snapper etc. nearby or fish from the park at the canal or from the dock at the house.

- "Barely used the house due to the wedding we were attending. the house was Very clean and Comfortable. Very retro ;0) would recommend to friends and family. " - "Perfect getaway especially for boat owners." - "Andrew and Jane made for a fantastic weekend. The property is exactly as described - conveniently located near the S Ferry and right on the water. The veranda provides a gorgeous backdrop and the house was excellent for weekend getaway. Jane made our check-in and check-out very easy and Andrew was quite accommodating re:assurances in the midst of the pandemic."

Shelter Island House features a seasonal outdoor swimming pool, garden, a shared lounge and restaurant in Shelter Island Heights. With a bar, the 4-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. Guests can have a drink at the snack bar. At the hotel, every room comes with a closet. Some rooms here will provide you with a kitchen with a fridge. All guest rooms at Shelter Island House are equipped with a flat-screen TV with cable channels and a safety deposit box. The accommodation has a sun terrace. Guests at Shelter Island House will be able to enjoy activities in and around Shelter Island Heights, like cycling. Long Island MacArthur Airport is 55 miles away.

Balcony/Terrace • Security/Safety • Bar • Entertainment • Guest Services • Wellness Facilities • Sports/Activities • Restaurant • Pool • Internet • Parking • Air Conditioner

Adults-only bed & breakfast with free breakfast and a seasonal outdoor pool
Coffee/tea in a common area, a seasonal outdoor pool, and free use of bicycles are available at this smoke-free bed & breakfast. Free continental breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, a garden, a picnic area, and a front-desk safe are onsite.
West Neck Guesthouse offers 6 air-conditioned accommodations with coffee/tea makers and bathrobes. Beds feature premium bedding. Flat-screen televisions come with cable channels.

Bathrooms include shower/tub combinations and complimentary toiletries. This Shelter Island Heights bed & breakfast provides complimentary wireless Internet access. Additionally, rooms include irons/ironing boards and ceiling fans. Housekeeping is provided daily.

- "Very convenient location next to Cresent Beach and Leon 1909 restaurant which is fantastic! " - "Lovely room - clean, comfy bed, luxury mattress, sheets, etc., attractive decor, spacious bathroom with natural light and fan to dehumidify the space. Outside area could be spruced up with plantings, better shaded area to sit, etc. Overall, lovely. Service was warm and responsive." - "Lovely room. Very clean. Easy parking. Used the pool at reciprocal property. It was lovely. "

Private Waterfront Home: Dock, Kayaks offers accommodations in Southold, 22 miles from Splish Splash. Both free Wifi and parking on-site are accessible at the vacation home free of charge. Private Waterfront Home: Dock, Kayaks features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are available in the vacation home. The accommodation has a fireplace. Long Island MacArthur Airport is 43 miles from the property.

View • Child Friendly • Parking • Internet • Air Conditioner • Security/Safety • Fireplace/Heating • Pet Friendly

While you're here, you can enjoy all the comforts of home and more, including free WiFi and a garden, as well as air conditioning and an ironing board. Other amenities include towels, a ceiling fan, luggage storage, and free toiletries.

- "Amazing location. Lovely lake. Serene and Tranquil experience. " - "The owner is very friendly and helpful. He even upgraded the room without additional fee. The rooms are so clean and organized with nice thick towels and amenities. Free coffee and tea were available with a water server, microwave, and a little sink to wash dishes. The area is so quiet and peaceful although some good restaurants and ferry port are in walking distance. Highly recommended. "

Featuring a garden, Sandpoint by Rove Travel Modern 5BR Family Home with Pool offers accommodations in Shelter Island. Guests are welcome to go for a swim in the private pool. With free Wifi, this vacation home features a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are offered in the vacation home. For added privacy, the accommodation features a private entrance. Westerly State Airport is 49 miles from the property.

View • Pool • Air Conditioner • Security/Safety • Fireplace/Heating • Parking • Child Friendly • Internet

Enjoy the beauty of Long Island's North Fork right here at our vacation house in Southold. Enjoy fabulous water views, boating, beautiful beaches, hiking, bicycling, discover wine country and so much more! Summer stays go from Sunday to Sunday or you can visit on weekends all other times of the year.
Our waterfront vacation home has a beautifully situated outdoor hot tub (on year-round), a large deck overlooking the water, a large flat yard, a waterside fire pit/patio with firewood provided, an outdoor shower, a park style charcoal grill, a gas grill and a quiet front porch for relaxing. Inside there are 3 full baths (a Jacuzzi in one of them), 4 large bedrooms, a fully stocked and beautiful kitchen and an open floor plan, WiFi, central air conditioning and a gas fireplace. The upstairs master bedroom has an outdoor veranda which overlooks the water. There’s plenty of room!
You can hang out on the deck and have a family BBQ. Play yard games or go for a ride on your boat right from the floating dock. If you bring your boats or watercrafts you can use the boat ramp that is right in the back yard. Feel free to use our kayaks, canoes, stand up paddle board or paddle boat.
The house is also located on a private gravel road with literally no traffic. You can rest assured that you and your children can safely walk to the beautiful bathing beach which is a short block away. Not only can you relax while watching the boats going by, but you will also find the most amazing shells of all kinds. Your kids can safely play and explore the beauty of all Southold has to offer!

Town of Southold Rental Permit # 0591
County of Suffolk Hotel Motel Tax ID: HMT23-10061

Keywords: House Waterfont Beach Boat ramp

- "This location delivered against everything listed and more. Dock for boat, water toys and central to all NOFO. We hosted my parents and cousins. A very special family get together spot. We biked to the vineyards and boated the Peconic Bay. Thank you Mike for all. We will be back and highly recommend!" - "Our second year in this wonderful property mike is a terrific host. If you can't enjoy yourself here you probably need a psychiatrist."

Relax on the large wrap-around front porch of this Long Island, New York bed and breakfast. Free Wi-Fi and daily breakfast are offered. Cedar Beach is 1 mile away. Each uniquely styled room at A Walk in the Woods Bed and Breakfast features private bathroom. Decorated with antique accents, these rooms include a seating area. This estate is located directly on the 14 mile Bayview bicycle loop. Pindar Vineyards is 5 miles away.

- "Can’t wait to go back!" - "We will definitely be going back!" - "Excellent place to stay"

1896 Restored Victorian located within steps to a lovely Bay Beach. Village restaurants, shops, NYC Hampton Jitney Express Bus and Shelter Island Ferry are all within a short stroll. Fresh produce farms, vineyards, hills and fields surround this very special place to rejuvenate your spirit and have fun. Fishing off the pier, sun bathing, swimming and people watching are all available within a two minute walk. Orient State Park is within a few miles and also offers nature lovers breath taking views of birds and marshes as well as the Long Island Sound. Also in Orient is a Sea Jet Ferry available to those who may want to enjoy the Mohegan Sun Casino in Connecticut across the Long Island Sound or travel north.

Private and spacious accomodations for four adults include two bedrooms each with a separate living space and a fully equipped kitchen and bath decorated in a casual antique pine style. Our charming second floor apartment is peaceful, perfect for two couples or a family.

2021 HVAC upgrade includes UV /HEPA airflow filtration. Exterior security cameras offer added measure of safety during your stay.

Typical Day : Easy to rise in the morning and have a cup of coffee in the garden ..take a stroll down to the beach and people watch.. come back..get ready for the day..

Leave the 'House'.. walk left toward the village and turn right on Clark Street ..now take a three block walk to the village along fourth street and the bay..enjoy the many restored village homes and the simple life..
So... are you ready to explore the village? The antique Carousel on Front Street..antique shops..maybe a cup of stronger coffee at Aldo's...
Stroll up and down Main Street..and Front Street and find your favorite shops/spots...Book, Toy, Cooking, Clothing......Art Galleries..Restaurants...Antiques...something for everyone.

- "We spent a wonderful 5 days in this beautiful home. John and Maritza are the most gracious hosts, offering recommendations and good cheer. The house is 1/2 block from the beach, or 1 block to the lagoon, which we also enjoyed. It is approximately a 15 minute walk or quick drive into town. The home is ideally situated. The kitchen was well-stocked with utensils, cookware and dishware; each bedroom has a sitting room/living room so there is plenty of privacy. Would love to return to this lovely home!"

Happiness Comes in Waves is situated in Southold, 1.6 km from Cedar Beach County Park and 37 km from Splish Splash, in an area where cycling can be enjoyed. It has a garden, a terrace, sea views and free WiFi throughout the property. The air-conditioned holiday home consists of 4 bedrooms, a living room, a fully equipped kitchen with a fridge and a coffee machine, and 3 bathrooms with a shower and free toiletries. Towels and bed linen are available in the holiday home. The nearest airport is Long Island MacArthur Airport, 72 km from the holiday home.

Balcony/Terrace • Internet • Pet Friendly • Air Conditioner • Kitchen • Parking • Child Friendly

This charming and newly renovated 3 bedroom, 2 bath ranch style home is located on a quiet street close to both Sunset and Shell beaches and within walking distance to Silver Beach off of Bootleggers Alley. We have bikes on hand to help you reach these and other beautiful destinations around Shelter Island. In the spacious backyard, which backs up to a nature preserve, you’ll find a brick patio with outdoor furniture, plenty of sun to sunbathe, lawn games, and an enclosed outdoor shower.

The master bedroom has a king-sized bed, en suite bathroom, and french doors that open to the serene privacy of the back yard. The second bedroom has a queen-sized bed, and the third bedroom has two twins – perfect for children or to share. Each bedroom has large closets and plenty of storage space. The hallway linen closet has towels for both bath and beach, sheets, and other comforts.

The living room, which features a large bay window, has a plush and comfortable couch and matching love seat that both pull out for additional sleeping space. The formal dining room has a sizable table that fits up to 10 guests and a set of french doors opens to the park-like back yard. The kitchen, which has great counter space, also has a benched bay window overlooking the backyard, and all the conveniences of home: a dishwasher, an oven, a Keurig coffee machine, a toaster oven, a microwave, and all the necessary items to cook and host. Just off the kitchen is a den that’s stocked with board games and an entertainment system, as well as a cozy, exposed brick gas fireplace. The den’s sectional sofa also pulls out to create another sleeping space. Finally, the laundry room has both a washer and dryer and is connected to the one car garage. Bookings over the summer months are Saturday to Saturday.

- "We thoroughly enjoyed our sun filled time in such peaceful surroundings. Beautiful Silver Beach home satisfied our three C’s of hospitality! The house was 1) Clean; 2) Charming; and 3) Convenient to everything! Thank you, Ashley!!" - "This home was as advertised- renovated, quiet and private. Excellent for bike riding. In a perfect location for many beaches and restaurants. (We attempted to try them all!). A well equipped kitchen for those rainy days. Our host was just an email away for any questions, with an impressive response time for those questions. We really felt at home away from home. Thank you!"

West Neck Guesthouse in Shelter Island Heights provides accommodations with free bikes and a garden. This guest house features free private parking, daily room service, and free Wifi. Outdoor seating is also available at the guest house. The guest house will provide guests with air-conditioned units with a wardrobe, a safety deposit box, a flat-screen TV, and a private bathroom with a bath. There's also a well-equipped kitchenette in some units equipped with an oven, a toaster, and a stovetop. At the guest house, every unit comes with bed linen and towels. Long Island MacArthur Airport is 55 miles from the property.

- "Nice location with plenty of privacy." - "So wonderful" - "Fabulous, fabulous, fabulous, in one sentence." - "We had a great time and would highly recommend." - "Would definitely stay there again!" - "Would go back next year!" - "Overall average." - "Great place to stay for short term." - "Clean and relaxing but property could have been much better if kept up to date and things worked."

Enjoy a charming 3 bedroom/2 bath with central AC on an expansive shy acre corner plot located directly across from Sylvester Manor Farm. The land across the street is a preserve and the adjacent lot is undeveloped which allows for plenty of relaxation and privacy. An 800 sqft (open plan) great room with two balconies and large windows is perfect for entertaining or lounging with a good book. The rear balcony descends to a gravel patio area with a fire pit, dining area and charcoal BBQ grill. Owners are very reasonable, responsive, and pet friendly!

About the Area: Shelter Island is unique to Long Island's east end because it's only accessible by ferry. Upon arriving in S.I you truly feel like you are in a different world with vacation mode fully setting in. You may be happy to hear that the island has been dubbed the "un Hamptons" by some because of its low key, relaxed and quiet atmosphere. Shelter Island is home to the 2,100 acre Mashomack Preserve which contains about 10 miles of coastline and represents 1/3 of the island. There you find breathtaking views of fields, creeks, and shoreline. If you are in the mood for an adventure, hop on the north ferry towards Greenport or the south ferry towards Sag Harbor and The Hamptons.

Additional notable amenities:

-Queen sized air mattress

-Workstation with WIFI and a new printer/scanner

-New 55" smart TV with Netflix etc.

-Charcoal BBQ grill

-Hammock

-12 cup coffee machine

-New washer/dryer

-Working fireplace

-Outdoor patio set

-Walking distance to mini golf

-Located close to marina & beaches.

- "Really lovely stay. Bathrooms and bedrooms newly renovated. Andrew was really helpful with the info for the house and local amenities. Great wifi. Great stay." - "Andrew’s place was perfect for our little family vacation at the beach." - "While staying in Shelter Island before, it was our first time staying here and overall have only amazing things to say! The house itself was very cozy and the fire place was such an amazing touch. Very clean and easy to check in, great communication with owner, and very accurate listing in a great location. Hope to visit again soon, Thank you!!!"

Located in Southold, within 49 km of Montauk Point Lighthouse, Private Waterfront home Dock Kayak walk to Southold, near Greenp offers accommodation with air conditioning. It is set 35 km from Splish Splash and offers a 24-hour front desk. The holiday home is fitted with 3 bedrooms, 2 bathrooms, bed linen, towels, a TV with satellite channels, a dining area, a fully equipped kitchen, and a balcony with sea views. If you would like to discover the area, skiing is possible in the surroundings. The nearest airport is Long Island MacArthur Airport, 70 km from the holiday home.

Parking • Child Friendly

Score Big at our fabulous Hamptons Cottage where work meets play in style! Settle into this charming 1700’s cottage nestled on 7 private acres of lush greenery adorned with majestic trees-your very own oasis! There are steep steps up to the second floor.
* Excellent Wifi: Say goodbye to buffering and hello to productivity with top-notch Wifi, ensuring seamless work-from-home sessions!
*Poolside Paradise: Dive into relaxation mode with a heated saltwater gunite pool-the ultimate spot to soak up the sun and splash around. Plus, keep an eye out for our resident turtles and frogs in the pond! Propane usage will be charged after stay.
*Cozy pool house: Need extra space? Our pool house offers an additional bedroom, kitchenette and a half bathroom-perfect for guests or a private retreat!
* Outdoor Delights: Rinse out in style with an invigorating outdoor shower, then unwind on the screened-in-porch-an ideal spot for sipping your morning coffee or enjoying evening cocktails.
*Modern Comforts: This cottage is equipped with all the bells and whistles, including a recently installed chef's kitchen, A/C, heating, and a Sonos sound system-ensuring your stay is as luxurious as it is comfortable.
*Beach Bonanza:
Just a ten minute stroll lies Wades Beach, beckoning you with its sandy shores and sparkling waters-paradise found!
With room to accommodate up to 10 guests, this dreamy cottage is your ticket to an unforgettable Hamptons getaway. So grab your bags, grab your laptop, and get ready to blend work with pleasure like never before! Ahhhh Shelter Island!!

- "Ingrid and her place was just amazing!!! My family and I do a yearly vacation and this was our first time visiting Shelter Island. The property was three minutes from the south ferry, which was super convenient. The grounds were extremely spacious filled with wild life and nature!! The pool was just perfect!! The house was able to fit all 10 of us with myself and my husband staying in the very cute and private pool house which is separate from the main house. Highly recommend staying at this property! Looking forward to booking this place again in the future!!"

Same location I have two 2 cottages that sleep 4 each . See VRBO search bar [Where To] with the Listing ID 173361 and the Listing ID 167288.

The centerpiece of this family owned waterfront estate, “The Main House” is a neo-victorian 5-bedroom, 3-bathroom sauna room and outdoorshower charmer that comfortably sleeps 8 - 10 people.

The panoramic porch with stunning water views, the spacious living room, the large dining room and kitchen and expansive outdoor patio and deck make this vacation paradise one of a kind.

Whether you’re planning a family reunion or looking to escape to the natural wilderness of the North Fork, this house has it all. Stroll along the estate’s private beach or have picnic overlooking the water.

The beautiful tree filled grounds are complete with pristine views of the bay and Shelter Island. With room to roam and nature to explore, the property is both kid and pet friendly. The house is fully furnished and linens are provided.

The house is quiet and secluded, yet within easy walking distance to Greenport Village, offering the best of both worlds.

With a strong nautical history, Greenport is a water-lover’s paradise and the perfect destination for sailing, boating, fishing, swimming, kayaking, and canoeing. Mitchell Park Marina is just a short walk from the estate and provides transient slips by the day or week.

Please call in advance for reservations to secure your spot.

While downtown in the village of Greenport, explore the local boutiques and stores. Take advantage of the history-rich Railroad, Stirling–Ireland House, and East End Seaport museums.

Ride the antique carousel, or take a tour of the harbor on The Glory, an electric launch. Sample the local bounty from land and sea in a variety of restaurants offering casual fare to award-winning dining.

Tour the over 42 vineyards located here on the North Fork. Discover the art galleries featuring local and international artists who represent the contemporary to the classic. So much tucked into one square mile and all conveniently within walking distance!

Greenport's proximity to Manhattan, Connecticut, and the South Shore means you don’t have to go far to get away. Enjoy a casual drive from the city, or let the LIRR or Hampton Jitney carry you here stress free.

Either way there is something for everyone, so come and experience what makes Greenport charming and unique. For more information about Greenport and all it has to offer, please visit the official village website supported by the Greenport BID. Make sure to enter Greenport Village in your search.

The estate also offers additional accommodations that when combined can be perfect for family gatherings. Please visit listing #173361--and--167288

Keywords: House

- "My family and I stayed for a week in the main house with 6 adults and 2 kids under the age of 4. It was perfect! The house is very spacious and charming. Almost every room has a view of the water. It was a perfect spot for the kids since it was steps from a private beach with very calm water (the only waves were from boats passing off shore). Perfect for littles! It is also close to downtown Greenport. We chose to drive into town, but you can easily bike or walk. We really loved staying here and plan on coming back next year! Pat was a gracious host. He met us upon check-in, and was easily accessible during our stay. He makes you feel welcomed and at home. You can really tell how much he loves this property and how special it is to his family. The main house is filled with family pictures and his artwork, which made it feel homey and welcoming. Thank you, Pat for helping our family create lifelong memories!"

Discover this marvelous 2-bedroom gem in Greenport. This cool apartment boasts a cozy living room with a phenomenal sofa bed, perfect for extra guests. The bedrooms offer a comfortable queen bed and a full bed, ensuring a restful night's sleep for all. With amenities like a washing machine, hair dryer, AC, heating, iron, and WiFi, you'll have everything you need for a delightful stay. The bathroom is equipped with a hair dryer for your convenience. This newly renovated 2 family home is in walking distance to all the restaurants, bars, shopping, coffee shops, Shelter Island Ferry, Log Island railroad and Hampton Jitney.
Guests are 4 blocks from the local beach which provides parking at no cost. Beach chairs and umbrellas are provided in the backyard. Washing Machine and Dryer are located in basement. Enjoy your time in Greenport at our apartment.

This property has two apartments. The Blue Bay Dream Apt. 1 and Harbor Heights Apt. 12 (see listing on VRBO website that can accommodate 12 people when available at the same time for larger families and wedding parties

Harbor Heights is the second floor stair walk up apartment.

- "We had an absolutely wonderful stay in this apartment - it is cozily decorated, spotlessly clean, the kitchen is extremely well stocked (Keurig machine with K cups - for all the coffee fiends like us 😁 - plus anything else we needed), the hosts thoughtfully left lists of recommendations and sightseeing and food along with all the local papers, and the location is unbeatable - a short walk to Greenport town, the marina, and the beach. We were four adults and two kids and we slept comfortably between the two bedrooms + sofa bed in the living room. Highly recommend this stay and looking forward to visiting again! THANK YOU to our hosts!"

This 2-bedroom house in Greenport with modern amenities for stylish uncluttered living. Perfect for a small family or couples and conveniently located in a quiet neighborhood near town, park and beach.

- "The house was spotlessly clean and well-maintained, making me feel comfortable right from the start. The location was perfect—local attractions and great restaurants, which made exploring the town very convenient. Walter was incredibly responsive and accommodating, always quick to reply to any questions or requests. Overall, I highly recommend this home for a friendly and hassle-free stay!" - "Our family were completely overjoyed by our week in this beautifully decorated and updated farmhouse. Sitting on the porch, grilling in the backyard, strolling to the beach and walking into Greenport were all this gem offers and much more. Couldn’t be happier with the communicative host. Highly recommended. "

Country Ranch five minutes to Mashomack Preserve hiking trails, beaches and miniature golf. Features include a living room, kitchen, dining nook, master bedroom(Queen bed), bathroom and guest bedroom with 2 twin beds, and washer/dryer. Pretty corner lot with a nice deck with a grill and seating for 5.

- "The property is old but it was clean. It does need new wallpaper and paint. The beds were very comfortable." - "Beautiful home on Shelter Island. Very comfy chair and couch in the living room, and comfy beds. The listing doesn’t mention the two TVs with basic cable, one in the living room and one in the bedroom with two beds. Very good location—walking distance to IGA supermarket, diner (try the ribs), and mini golf. Terence was kind and eager to help. Great price. Good kitchen and decor. My family had a wonderful time! We are already thinking about coming back next summer."

Sweet Southold Beach Cottage
Spring/Summer/Fall/Winter

Prime location! View Peconic Bay from your driveway! One minute walk to the BEACH at Founders Landing. A classic, North Fork renovated 2 bedroom small cottage. The petite, airy cottage with a mini split AC, 3 ceiling fans and 10 windows. Open floor plan includes a kitchen with stainless steel appliances, a counter with stools that opens to the dining area. Refreshing coastal/outdoor living includes a deck with grill. Make it your easy, breezy getaway.
Design your rental package.

MONTHLY: May 3.5k, Ju 4k, Jul 7k , Au 8k, Sep 4k
MD-LD 19k
JULY/AUG-LD 15k

WINTER 2024-2025 Oct- April 3k/mnth+util

Contact me with questions and Multiple Month Rate discount. Rates are based on a monthly rental.

Relax and enjoy the beautiful sunrise on the beach. The property is setback from the road and is on a 1/4 acre. The landscaped yard has a spacious rear deck . The petite and airy cottage has an open floor plan with a mini split AC, 3 ceiling fans, and 10 windows that let the coastal air in. The kitchen with stainless appliances and a counter with stools opens to the dining area. The cozy living room with vintage rolling doors is the perfect spot to have a morning cup of coffee as the sunrises, that’s if you don’t want to sit on the small front deck outside and see hummingbirds. The main bedroom has a large closet and laundry access. The sweet beachy bathroom includes a tub/shower, and a vintage rolling door. Enjoy the coziness of the space that embraces true North Fork coastal living.

MONTHLY: May 3.5k Ju 4k, Jul 7k , Au 8k, Sep 4k
MD-LD 19k
JULY/AUG-LD 15k

WINTER 2025-26 Oct- April 3K/month.+utl

Contact me with questions and Multiple Month Rate.

Guest Access
Kitchenwares for cooking. WiFi/Wireless internet. Bring your device to stream. 2 car driveway, house, back deck, front deck. Outdoor gas grill. Beach chairs. Bring your bikes and kayaks.

Looking forward to welcoming you. I can advise you regarding any of your interests locally and I'm happy to do so. Your privacy is respected. I may be on site to maintain the property.

The Neighborhood
Beach and water view at end of the driveway! Take a dunk before dinner. Put in your kayak or boat at the ramp. Swim at Founders Landing lifeguarded beach at end of road. The Boat Yard Marina is also at the end of road. Southold has many places to eat, small local shops, wineries and a brewery. Great hiking trails as well. Birding, Fishing, Golf, Pickleball, tennis, antiques, and rustic finds. Neighborhood is great for walking and biking and friendly faces. The North Fork offers farmstands, organic seasonal and fresh foods. Many live music venues, great restaurants and attractions.

Getting around
Walk to Southold LIRR station. Walk to Hampton JITNEY Southold. Boat. Walk to town of Southold. Local transportation includes: Car services, Uber, Lyft, bike rentals or Bring your bike. Ferry to Shelter Island, Connecticut or Sag Harbor.

Other things to note:
You are asked to be mindfull of the environment. Small dog considered. Rates are based on 2 person occupancy.
Monthly discounts are available. this property is a legal rental.

Please read the listing carefully including details.

- "We spent a week in early August at this beautiful little cottage in Southold. What a gem!!! The house is beautifully decorated and was very clean. There was everything we needed. A small private beach with lifeguard is at the end of the road 2 minute walk. We are a family with two young children aged 2 and 6 and the size of the cottage and the quiet beach with a small playground were perfect for us. The owner of the property is wonderful and gave us great tips for the area. Highly recommend a stay here! We will be back. "

Enjoy the best that Shelter Island can offer at this renovated 2 bedroom waterfront gem.
Nestled on West Neck Bay, this one-of-a-kind home is just 20ft from the water with sweeping views.
Wake up to the amazing dawn rising above the water and flooding the patio outside the master bedroom.
Take a morning stroll to bootleggers' beach or simply hang out on the dock.
After breakfast, sit and enjoy the views or rent some Kayaks and explore the bay and beyond.
Then there's swimming off the dock (no diving though as the water is shallow), clamming, reading, relaxing...And so it goes on until it's time for a picnic or an outdoor BBQ with your friends who've just sailed over from Sag Harbor and anchored off your dock.
And of course, if you can tear yourself away from this little piece of heaven there's the whole of Shelter Island and beyond to explore before coming back to evening cocktails on the porch, more views and dinner around the table.
You may never need it, but just in case there's also cable TV, stereo and all that.
Be warned - you may never want to leave :-)

License 014 - twenty seventeen

- "Lovely spot, great location and very warm and charming. Would most definitely return"

This furnished bright one bedroom is perfect for your escape to Shelter Island.
Queen bed and 1 bathroom
Kitchenette with fridge, freezer, coffee maker and sink
XL Smart TV
WiFi
AC
Beach chairs
Linens
Weekly maid service & Laundry service

Fireplace/Heating • Internet • Other • Bedding/Linens • Security/Safety • Air Conditioner • Wellness Facilities • Tv • Laundry

Adorable studio with private entrance located on a quiet road. Kitchenette and large open living area with great natural light. Access to inlet perfect for kayaking, paddle boarding or watching sunset. Centrally located so easy to get to all that Shelter Island offers.

Bedding/Linens • Security/Safety • Tv • Laundry • View • Kitchen • Oceanfront • Wellness Facilities • Air Conditioner • Other • Ocean View • Fireplace/Heating

Stunning location on 8 waterfront acres at Dering Harbor Inn. Newly refurbished condo with peaceful private deck overlooking the harbor and boats. Big bedroom and en suite bathroom with shower and tub. Fully functional retro kitchen. Saltwater pool. 2 free parking spots. WiFi. TV. AC. Tennis and large gym also available to rent. 5 minutes walk to harbor, Marie Eiffel market, liquor store, and bike rental.

MINIMUM STAY 1 WEEK PLEASE. SATURDAY TO SATURDAY.
ALSO AVAILABLE YEAR ROUND.

Laundry • Parking • Internet • Bedding/Linens • Pool • Wellness Facilities • Security/Safety • Kitchen • Air Conditioner • Other • Barbecue/Outdoor Cooking • Tv

Shelter Island Gem

Chic Shelter Island A-Frame with Private Pool, Stylish Interiors, and Resort-Style Outdoor Living

3BR/2BA: Private Heated Pool, Expansive Fenced Yard, Outdoor Dining & Shower, Fire Pit, Seamless Indoor-Outdoor Living

Welcome to a stunning blend of charm, sophistication, and coastal style at this impeccably designed Shelter Island A-Frame home. Perfectly situated in a central location, guests will find themselves just moments from the islands beloved restaurants, shops, bars, and pristine beaches. This elegant hideaway offers the ideal backdrop for families, groups, or anyone looking to truly escape daily life and immerse themselves in the relaxed spirit of Shelter Island. With three bedrooms, two bathrooms, and room for up to six guests, this residence boasts double-height ceilings, abundant natural light, a stylishly updated kitchen, and thoughtfully designed interiors. Equipped with all modern conveniences including WiFi, air conditioning, a washer and dryer, and a dedicated work-from-home space, this home masterfully combines comfort with luxury island living.

Outside, the private, expansive fenced-in yard creates a true sanctuary. Guests can bask in the sunshine by the private heated pool, where chaise loungers invite relaxation throughout the day. A charming pool house provides additional living space for lounging or quiet moments away from the main home. A beautiful wooden sundeck offers a seamless connection between indoor and outdoor living, complete with an outdoor shower with hot and cold waterperfect for rinsing off after a refreshing swim or beach day. Evenings are made magical around the fire pit with Adirondack chairs, ideal for cocktails, storytelling, and stargazing. Multiple outdoor seating areas encourage leisurely afternoons and intimate conversations, while outdoor dining spaces invite memorable alfresco meals. Ample free parking ensures convenience for all guests throughout their stay.

Upon entering the A-frame home, guests are greeted by an airy, open floor plan flooded with natural light. The main living area flows effortlessly into the dining space and kitchen, creating a communal atmosphere perfect for gathering. Sliding glass doors off the dining room open directly to the backyard oasis, further blending the indoors with the beauty of the surrounding outdoors. An additional sunroom, framed by walls of windows and furnished with two plush sofas, offers a cozy and serene spot to unwind, with direct access to the sun deck through sliding doors. The updated kitchen is fully equipped with everything needed to craft a home-cooked meal, including modern appliances, a coffee maker, and a complete array of cooking essentials. Every detail throughout the interiors has been carefully selected to offer a stylish, comfortable, and inviting environment.

The home offers three beautifully appointed bedrooms and two sleek, modern bathrooms, ensuring every guest rests in absolute comfort. Two bedrooms are conveniently located on the main floor, each featuring a queen bed outfitted with fresh, luxurious linens and thoughtful touches for a restful night's sleep. A lofted third bedroom offers a charming and private retreat, also with a queen bed. The primary bedroom boasts direct access to the sun deck and an en-suite bathroom complete with a spacious walk-in shower. An additional hall bathroom, also featuring a walk-in shower, serves the other bedrooms. Both bathrooms are newly updated, fully stocked with plush towels, and equipped with all the essentials needed for a seamless stay.

Beyond the property, the heart of Shelter Island awaits. Guests can easily explore a variety of local treasures, many just a short drive or leisurely bike ride away. Discover charming boutiques, art galleries, and locally loved restaurants offering everything from farm-to-table fare to fresh-caught seafood. For those looking to connect with nature, Shelter Islands beautiful beaches provide the perfect escape for sunbathing, swimming, and water sports. Outdoor enthusiasts will appreciate nearby golf courses, scenic nature preserves, and hiking trails. The islands many farm stands and markets offer fresh, local produce to bring back and enjoy at the home. For wine lovers, several acclaimed wineries are within easy reach, offering tastings and tours in picturesque vineyard settings. Whether guests seek adventure or relaxation, this location offers something for every mood and moment.

This Shelter Island A-frame invites you to slow down, breathe in the sea air, and create unforgettable memories in a setting that feels both luxurious and effortless. Your island escape awaits.

This property has a max occupancy of 6

Bedrooms

Bedroom 1 - Primary: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom

Bedroom 2 - Guest: One Queen Bed, First Floor/Main Floor, Air Conditioning, TV, Standard Closet

Bedroom 3 - Guest: One Queen Bed, 2nd Floor, Air Conditioning

Bathrooms

Bathroom 1 - Primary Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Handicap Accessible, Shower

Bathroom 2 - Hall: Full Bath, First Floor/Main Floor, Handicap Accessible, Shower

TVs

Bedroom 2 - Guest

Outdoors & Pool/Spas
Deck/Patio (Uncovered), Outdoor Shower (Hot + Cold Water), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Fence Around The Pool, Fence Around The Yard, Fire Pit (Wood), Private Pool (Heated, Outdoor, Saltwater)

Amenities
Bed Linens, Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Hair Dryer, Living Room, Parking, Coffee (Other), Dishes and Silverware, Pots and Pans, Toaster, Speaker System (Sonos), Television, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Fire Extinguisher, Essentials, Laptop-Friendly Workspace, Bath Towels, Pool/Beach Towels, Private Entrance, Blender, Smart TV, Privacy (Completely Private)

Location

Nearby Beaches:
Shell Beach
Wades Beach
Crescent Beach

Nearby Grocery Stores:
Haven's Farmer's Market
Sep's Farm Stand
Elli's Country Store
IGA Shelter Island

Nearby Restaurants and Bars:
Shelter Island Craft Brewery
SALT Waterfront Bar & Grill
18 Bay
Osprey Bar & Lounge
Sunset Beach
The Islander

Other Location Information:
Mashomack Preserve
Fresh Pond

Suitability: Not handicap accessible.
Primary renter must be at least 30 years old.

Pet Policy: One dog of 50 lbs or less is permitted for an additional $250.00 per booking. Dogs over 50 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire).

Utility Disclaimer:
Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $100.00 per night of the reservation.

Cleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest's expense.

Additional Guests: No additional guests beyond the max occupancy of this listing are permitted.

Events Policy: Events are prohibited

Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed.

Pool Disclaimer: Due to the climate of the northeastern U.S outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking.
For energy conservation purposes, the pool heater may only be operational from 8am to 6pm.

Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking.

Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Marquis will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners'). Should Marquis be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Marquis is notified in writing 72 hours or more prior to the start of the reservation.

Note: All payments must be made prior to check-in.

VRBO charges the guest directly for their service fee and applicable taxes, while StayMarquis charges separately for the rental rate. As a result, you will see two separate charges at the time of booking-one from VRBO and one from StayMarquis.

If there is a second installment, it will be collected directly by StayMarquis shortly after the first installment.

Payment Method: Balance payments made with credit card are capped at $3,500. Payments over $3,500 shall be made by check, ACH or wire.

Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $5,000 of damage protection. Coverage details are provided in the booking agreement.

While StayMarquis manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, StayMarquis will provide you with a "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef.

Guest Experience: This property is part of our 'Elite' program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed.

Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Balcony/Terrace • Other • Security/Safety • Tv • Laundry • Parking • Oceanfront • View • Air Conditioner • Internet • Wellness Facilities • Kitchen

Nestled in the woods just behind the Pridwin Hotel, walk to Crescent Beach, Perlman Music and Sunset Beach.
1930''s Shelter Island original structure recently renovated.
Surrounded by nature.
.......

Balcony/Terrace • Ocean View • Sports/Activities • Bedding/Linens • Laundry • Wellness Facilities • Fireplace/Heating • Child Friendly • Kitchen • Other • Security/Safety • Tv

Formerly the Dering Harbor Inn, the cooperative unit offers a private eat on balcony, fully equipped kitchenette, dining area, pull out sofa bed, laundry facilities (coin-operated), cable TV and internet.
The 7 acre property offers an open-air swimming pool, Adirondack chairs on the bluff with gas grills for outdoor barbecuing overlooking the harbor, access to on premises fitness center and tennis courts, a fresh-juice and coffee bar, on site parking, walk to town, though you may never want to leave the property!

Security/Safety • Kitchen • Tv • Air Conditioner • Other • Pool • Fireplace/Heating • Internet • Bedding/Linens • Parking • Laundry • Wellness Facilities

Enjoy a stylish experience at this centrally-located historic charmer. Have cocktails on the balcony, cook in the fully modern chef’s kitchen, grill and dine on the patio and enjoy the sauna. Walk to the beach and stop a local winery on the way home.
Close to Greenport and Southold.

Child Friendly • Security/Safety

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check in is 21 years old.

THE UNIT

This 215sf Hillside Room features:
- King bed
- TV
- In-room Nespresso machine
- In-room Beverage Chiller
- Views of surrounding grounds and cottages
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Wellness Facilities • View • Internet • Entertainment • Air Conditioner • Bedding/Linens • Security/Safety • Sports/Activities • Oceanfront • Wheelchair Accessible • Fireplace/Heating • Ocean View

Consider this lovely house your home away from home while you visit Shelter Island. With 3 cozy bedrooms, heating, and AC, this adorable property is perfect for a relaxing getaway. Beautiful, large 1.5 acre property with inground swimming pool is perfect for a family looking to enjoy the great outdoors. Experience what Shelter Island has to offer with a stay at our house!

Laundry • Fireplace/Heating • Child Friendly • Air Conditioner • Bedding/Linens • Internet

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check in is 21 years old.

THE UNIT

This 215sf Hillside Room features:
- King bed
- TV
- In-room Nespresso machine
- In-room Beverage Chiller
- Views of surrounding grounds and cottages
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Other • Security/Safety • Fireplace/Heating • Tv • Ocean View • Oceanfront • View • Accessibility • Kitchen • Spa • Laundry • Parking

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check-in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check-in is 21 years old.

THE UNIT

This 215sf Waterview Room features:
- King bed
- TV
- In-room Nespresso machine
- In-room Beverage Chiller
- Views of surrounding grounds and cottages
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Kitchen • Oceanfront • Tv • Fireplace/Heating • Accessibility • View • Ocean View • Laundry • Parking • Spa • Other • Security/Safety

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check-in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check-in is 21 years old.

THE UNIT

This 215sf Waterview Room features:
- King bed
- TV
- In-room Nespresso machine
- In-room Beverage Chiller
- Views of surrounding grounds and cottages
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Parking • Wellness Facilities • Other • Fireplace/Heating • Laundry • Wheelchair Accessible • Tv • Accessibility • Spa • Sports/Activities • Bedding/Linens • Air Conditioner

Discover Shelter Island's charm near Crescent Beach and Mashomack Preserve. Enjoy serene beaches, vibrant nature, and local delicacies, perfect for a tranquil retreat.

Experience peace and serenity in our elegantly designed room, where luxurious amenities blend with rich tradition. With nearly a century of history and a recent top-to-bottom renovation, our space captures the essence of a timeless resort ambiance. Enjoy access to a private balcony overlooking the bay, indulge in soothing spa services, or embrace adventure with our complimentary guest bicycles. Whether you're here for relaxation or exploration, our room provides the perfect retreat on Shelter Island.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- The property also requires a credit card, debit card, or cash deposit for incidental charges at check-in. Fees and deposits may not include tax and are subject to change.

- Early check-in is subject to availability upon arrival.

- To check in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check in is 21 years old.

THE UNIT

This Hickory Cottage features:
- King bed
- Living area
- Full sleeper sofa
- View overlooking wooded grove of trees
- Large covered front deck
- Gas fireplace
- Wet Bar-Style Kitchenette, equipped with a Nespresso machine, electric kettle, half-size refrigerator, and full hot and cold sink
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our timeless property offers you a historic and elegant resort experience with the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Spa • Parking • Tv • Fireplace/Heating • Other • Oceanfront • Accessibility • Kitchen • Laundry • Ocean View • Security/Safety • View

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check-in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check-in is 21 years old.

THE UNIT

This 230 sq ft Corner Preferred Room features:
- King bed
- Queen sleeper sofa
- Full water views of Crescent Beach and Shelter Island Sound
- In-room Nespresso machine
- In-room Beverage Chiller
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Ocean View • Spa • Fireplace/Heating • Oceanfront • Other • Laundry • Tv • Kitchen • Parking • Accessibility • Security/Safety • View

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check-in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check-in is 21 years old.

THE UNIT

This Hickory Cottage features:
- King bed
- Full sleeper sofa
- Private deck
- Full water views of Crescent Beach and Shelter Island Sound
- Gas fireplace
- Wet Bar-Style Kitchenette, equipped with a Nespresso machine, electric kettle, half-size refrigerator, and full hot and cold sink
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Oceanfront • Other • Spa • Parking • Ocean View • View • Tv • Accessibility • Kitchen • Fireplace/Heating • Laundry • Security/Safety

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check-in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check-in is 21 years old.

THE UNIT

This 230 sq ft Terrace Room features:
- King bed
- Outdoor covered deck with view of Crescent Beach
- In-room Nespresso machine
- In-room beverage chiller
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Other • Fireplace/Heating • Accessibility • Parking • Tv • Spa • Laundry • Oceanfront • View • Security/Safety • Kitchen • Ocean View

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- These are TWO separate hotel rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check-in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check-in is 21 years old.

THE UNIT

This 215sf Waterview Room features:
- King bed
- TV
- In-room Nespresso machine
- In-room Beverage Chiller
- Views of surrounding grounds and cottages
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Ocean View • Security/Safety • Air Conditioner • Bedding/Linens • Internet • Oceanfront • Wellness Facilities • Fireplace/Heating • Wheelchair Accessible • Entertainment • View • Sports/Activities

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- These are TWO separate hotel rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check-in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check-in is 21 years old.

THE UNIT

Each 215sf Hillside Room features:
- King bed
- TV
- In-room Nespresso machine
- In-room Beverage Chiller
- Views of surrounding grounds and cottages
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Tv • Oceanfront • Kitchen • Ocean View • Other • View • Accessibility • Laundry • Spa • Parking • Fireplace/Heating • Security/Safety

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check-in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check-in is 21 years old.

THE UNIT

This Birch Cottage features:
- King bed
- Full sleeper sofa
- Private deck
- Full water views of Crescent Beach and Shelter Island Sound
- Gas fireplace
- Wet Bar-Style Kitchenette, equipped with a Nespresso machine, electric kettle, half-size refrigerator, and full hot and cold sink
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Parking • Oceanfront • Fireplace/Heating • Spa • Kitchen • Ocean View • View • Accessibility • Other • Laundry • Tv • Security/Safety

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- These are TWO separate hotel rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check-in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check-in is 21 years old.

THE UNIT

Each 215sf Hillside Room features:
- King bed
- TV
- In-room Nespresso machine
- In-room Beverage Chiller
- Views of surrounding grounds and cottages
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Air Conditioner • Bedding/Linens • Tv • Spa • Sports/Activities • Wheelchair Accessible • Parking • Accessibility • Fireplace/Heating • Wellness Facilities • Other • Laundry

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check-in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check-in is 21 years old.

THE UNIT

This Larch Cottage features:
- King bed
- Living area
- Full sleeper sofa
- View overlooking wooded grove of trees
- Large covered front deck
- Gas fireplace
- Wet Bar-Style Kitchenette, equipped with a Nespresso machine, electric kettle, half-size refrigerator, and full hot and cold sink
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Accessibility • Kitchen • View • Parking • Ocean View • Fireplace/Heating • Spa • Laundry • Other • Security/Safety • Tv • Oceanfront

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- These are TWO separate hotel rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check-in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check-in is 21 years old.

THE UNIT

This 215sf Waterview Room features:
- King bed
- TV
- In-room Nespresso machine
- In-room Beverage Chiller
- Views of surrounding grounds and cottages
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Accessibility • Laundry • Spa • View • Fireplace/Heating • Oceanfront • Security/Safety • Other • Parking • Ocean View • Tv • Kitchen

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check-in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check-in is 21 years old.

THE UNIT

This Red Oak Cottage features:
- King bed
- Living area
- Full sleeper sofa
- Full water views of Crescent Beach and Shelter Island Sound
- Large covered front deck
- Gas fireplace
- Wet Bar-Style Kitchenette, equipped with a Nespresso machine, electric kettle, half-size refrigerator, and full hot and cold sink
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Accessibility • Other • Parking • Kitchen • Laundry • Spa • Oceanfront • Ocean View • Fireplace/Heating • Tv • View • Security/Safety

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check-in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check-in is 21 years old.

THE UNIT

This Red Oak Cottage features:
- Bedroom 1: King bed
- Bedroom 2: Queen bed
- Separate living area
- Full sleeper sofa
- View overlooking wooded grove of trees
- Gas fireplace
- Wet Bar-Style Kitchenette, equipped with a Nespresso machine, electric kettle, half-size refrigerator, and full hot and cold sink
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Ocean View • Other • Accessibility • Fireplace/Heating • Tv • Security/Safety • View • Spa • Kitchen • Parking • Oceanfront • Laundry

A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and live entertainment. Enjoy complimentary bicycles, tennis, and pickleball. Seasonal water sports, including kayaking and paddleboarding, offer adventure on the water.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- A credit card, debit card, or cash deposit is required at check-in for incidental charges. Fees and deposits may exclude tax and can change.

- Early check-in is subject to availability upon arrival.

- To check-in, bring your valid government-issued photo ID or passport to the front desk in the lobby. The minimum age required to check-in is 21 years old.

THE UNIT

This White Oak Cottage features:
- Features ground-floor bedroom with King bed
- Double-height living room with Queen sleeper sofa
- Lofted second-floor bedroom and bathroom
- Private deck
- Partial water views of Crescent Beach and Shelter Island Sound
- Gas fireplace
- Wet Bar-Style Kitchenette, equipped with a Nespresso machine, electric kettle, half-size refrigerator, and full hot and cold sink
- All linens, towels, and bathroom essentials are provided.

THE PROPERTY

Our serene property offers you a tranquil escape surrounded by natural beauty and the following on-site amenities:

- 24/7 Front desk and Security
- Heated Outdoor Pool (Available from Late May to Mid October)
- The Terrace (Water-view restaurant)
- Onsite Bar
- The Pridwin Spa (Reopening on May 9, 2025)
- Fitness Center
- Complimentary Bicycles
- Live Entertainment
- Game Room
- The Nook
- Concierge Services
- Tennis & Pickleball
- Water Sports (Complimentary stand-up paddleboards and seasonal guest activities such as tubing and kayaking)

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are not allowed.

Oceanfront • Ocean View • Kitchen • View • Parking • Spa • Fireplace/Heating • Tv • Laundry • Accessibility • Other • Security/Safety

Kick back and relax in this new, serenely decorated renovated space with private entrance. A short three minute drive to tan, swim and lunch at Sunset Beach or take a stroll along Bootleggers pictured here, just a ten minute walk from the house. Amenities include coffee, Nespresso machine, tea, beach towels and welcome beer, wine and hard seltzer.

Clothing storage: wardrobe • Hot water • Body soap • Bed linens • Hair dryer • Essentials • Organic Brand conditioner • Hangers • Organic shampoo • Shower gel

Access to endless pool/spa, private beach around corner, breathtaking views, access for kayak, sup etc on property, playful friendly dog, easy access to all including sunset beach, beautiful breeze, private location, 46 foot classic powerboat available for charter at discounted rate w/ rental

The space
Waterfront charming studio, private location access to 2acres of waterfront property paddle board, kayak, fishing, swimming

Guest access
Endless pool/spa, private dock

Other things to note
Welcome to bring bikes, kayaks, paddle boards etc, dock on property makes launching easy

Smoke alarm • Carbon monoxide alarm • Fire extinguisher • Heating • Hot water • Wifi • Hangers • Air conditioning • Indoor fireplace • Essentials

4BR/2BA - waterview, screened in porch perfect for dining inside and out, cedar outdoor shower

The space
Full waterview, across the street from the beach. Kayak access across the street. Very close to shell beach. Located in a corner lot, on a very quiet part of Shelter Island/Silver Beach.

Guest access
Access to entire property

Other things to note
Please note that a reservation for this property needs to be approved before it is confirmed.

East Brander Escape

Lovely Shelter Island cottage with panoramic bay views, secluded, screened porch, cedar outdoor shower, steps to the beach, access to kayaks and bikes

4BR/2BA - waterview, screened in porch perfect for dining inside and out, cedar outdoor shower

Gently tucked on a quiet street and steps to West Neck Harbor, a picture perfect Cape summer retreat full of Shelter Islands charm, sweeping bay views and beautiful outdoor space that is sure to be an unforgettable stay in Shelter Island. With direct access to the bay, prepare for outdoor activities galore including kayaking, canoeing, biking, picnics, nature walks or simply basking in the sun.

Spanning over 2,200 square feet, this contemporary home features a light-filled, open floor plan curated with cool blue hues, warm neutrals, panoramic water views and contemporary finishes sure to make you feel at home. The spacious living and dining room features a cozy fireplace to spend time with family and friends in. Settled just off of the living room is a peaceful den perfect for reading or quiet time. Showcase your skills or hire a private chef to come and prepare a lavish meal for the home as the gourmet kitchen includes your main cooking essentials. There are four tranquil bedrooms prepared with your warmth and comfort in mind. Each room includes fresh linens, plush towels and your main bath essentials. Additional amenities include a wood fire pit, beach chairs/umbrella and gas grill for summer BBQs.

Start and finish your day outdoors as you are surrounded by the tranquility of natures beauty and Shelters island relaxing ambiance. Wake up to your natural alarm clock and enjoy the sunrise from your cozy screened porch then head down the trail for fun in the sun. When youre ready to head into town, grab one of the bikes available and explore the North Fork. Conveniently located you are near a wide array of stellar local shops and restaurants as well as minutes from Shell, Crescent and Crab Creek Beach. East Brander Escape makes for the perfect summer enjoyment.

Separate Residence
Please note, there is a separate cottage on the property where the owner will likely be staying.

Please note: the sliding doors off the deck need to be pulled firmly to open.

This property has a max occupancy of 6

Bedrooms

Bedroom 1: One Queen Bed, 2nd Floor, Air Conditioning, Standard Closet

Bedroom 2: One Queen Bed, 2nd Floor, Air Conditioning, Closet

Bedroom 3: Two Twin Single Beds, 2nd Floor, Air Conditioning, Closet

Bedroom 4: Two Twin Single Beds, First Floor/Main Floor, Closet

Additional Sleeping Space: One Sleep Sofa, First Floor/Main Floor

Bathrooms

Bathroom 1: Full Bath, First Floor/Main Floor, Shower, Tub

Bathroom 2: Full Bath, 2nd Floor, Shower

Outdoors
Beach Chairs (10 Chairs), Beach Umbrella, Outdoor Shower (Hot + Cold Water), Deck/Patio (Covered), Patio Furniture (Table, Chairs), Bicycle (4 Adult Bikes), Grill (Gas), Kayak/Canoe, Fire Pit (Wood), Cooler, Fence Around The Yard

Amenities
Bed Linens, Bath Towels, Pool/Beach Towels, Air Conditioning (Window Units), Heating, Hot Water, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Usable Fireplace (Wood), Internet (Wifi), Microwave, Coffee (Pot, Other, Keurig), Dishes and Silverware, Pots and Pans, Toaster, Speaker System (Bluetooth Speaker), Television, Private Entrance, Living Room, Parking (4 Cars In Driveway), Pack 'n Play/Travel Crib, Kitchen, Stove, Oven, Refrigerator, Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Dishwasher, Cable TV, Essentials, Blender, Laptop-Friendly Workspace, Pots and Pans

Special Features
Full waterview, across the street from the beach. Kayak access across the street. Very close to shell beach. Located in a corner lot, on a very quiet part of Shelter Island/Silver Beach.

Location

Nearby Beaches:
Shell Beach, Crescent Beach, Crab Creek Beach.

Nearby Grocery Stores:
IGA on Island

Nearby Restaurants and Bars:
Dan Brock's Barbecue at Ellie's country store excellent sides and puddings in mason jars

Marie Eiffel- in the Heights a wonderful french patisserie with great take out food.

Ram's Head Inn-- always special even just for cocktails on the beautiful lawn in adirondeck chairs.

Kyles- fantastic homemade jelly and cinemon doughnuts croissants and cakes.

commander cody's-- great fish store, and fabulous barbecue-- pan fried chicken, and take out fish.

Vine Street Cafe-- excellent food, five stars.

maria's kitchen, great take out Mexican-- great homemade chips and guac.

Shelter island slice has decent pizza.

Other Location Information:
you don't need a parking sticker for the first half of crescent beach, which is about two miles away and also has a food truck.

Other FAQ's

Estimated Square Footage: 2,200

Rental Registration: 19S-0025.

Suitability: Not handicap accessible.
Primary renter must be at least 35 years old.

Pet Policy: One hypoallergenic, non-shedding dog of 50 lbs or less is permitted for an additional $250.00 per booking. Non hypoallergenic/shedding dogs or any dogs over 50 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire).

Utility Disclaimer:
Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $70.00 per night of the reservation.

Cleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest's expense.

Additional Guests: No additional guests beyond the max occupancy of this listing are permitted.

Events Policy: Events are prohibited

Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking.

Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $5,000 of damage protection. Coverage details are provided in the booking agreement.

This property requires a separate booking agreement to be signed by both parties before the reservation is confirmed. Please inquire prior to booking.

While StayMarquis manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, StayMarquis will provide you with a "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef.

Guest Experience: This property is part of our 'Elite' program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed.

Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

TV with standard cable • Hot water • Iron • Pack ’n play/Travel crib • Dryer • Washer • Air conditioning • Bed linens • Essentials • Hair dryer

Enjoy the tranquility of Silver Beach in this renovated and modern apartment with private entrance. Spectacular water views from all living areas. Walk to Shell and other local beaches. Ideal location for kayaking, paddle boarding, and bike riding. Enjoy the beautiful light at day's end from your private second-floor balcony.

The space
This modern apartment is impeccably clean and has all the amenities you'll need for a wonderful and relaxing vacation. There is a private entrance. A hot and cold outdoor shower is available for after beach refreshment.

Guest access
Launch your kayak, canoe, or paddle board, at the town landing, less than 1/4 mile away. Gloriously quiet Shell Beach is a relaxing walk or bike ride away. Famous Sunset Beach is just minutes by car.

Washer • Outdoor shower • Shampoo • Cleaning products • Body soap • Hot water • Free dryer – In building • Hair dryer • Beach view • Conditioner

Located on a private road & nestled in the woods, you’ll easily get lost in the quiet sounds & sights of nature all around you. Great walking/biking area, with the beaches less than a half-mile away. SI is a special example of the beauty on this earth! My 14 lb dog & I live in the separate converted garage. Your house has separate parking, a privacy fence & separate entrance, so you'll only see me if you need me. If you’re looking to escape, relax, & quiet your mind, you have found your home! ✨

Guest access
The entire home is yours ✨ No shared spaces.

Conditioner • Cleaning products • Free dryer – In unit • Shower gel • Hair dryer • Washer • Shampoo • Hot water • Essentials • Body soap

Lovely 3 bedroom ranch short walk to private beach in Silver Beach community of Shelter Island. Short drive to Sunset beach, shops and restaurants.

The space
Indoor space includes: kitchen/dining area, living room, 3 bedrooms and 2.5 bathrooms.
Outdoor space includes: outdoor rinse-off shower, gas grill, deck with dining set and chaises. On one acre property.

Guest access
This listing is for the entire home with the exception of a separate third car garage space and a basement.

Hot water • Hair dryer • Bed linens • TV • Washer • Free dryer • Essentials • Shampoo • Hangers • Iron

Enjoy summer on Shelter Island in this 3 bedroom, 2 bathroom, freshly painted and well equipped MCM ranch house on 3/4 of an acre. Located at the end of a private road, it's in walking distance to Shell Beach, town landings and a beautiful sunset viewing spot. Brand new, heated, inground pool w/ color changing light, central air, deck, fire pit and BBQ make this a great vacation home.

Ivory and Irish Spring body soap • Essentials • Bed linens • Cleaning products • Hangers • Hot water • Bathtub • Free dryer – In building • Free washer – In building • Extra pillows and blankets

Peconic Bayfront. Steps too Swimming- water sports -1929 cape completely renovated with central air. Crazy sunsets - sunrise

Other things to note
small dogs allowed at owners discretion. only small well behaved dogs on leash allowed

Cleaning products • Conditioner • Body soap • Bathtub • Shower gel • Washer • Shampoo • Outdoor shower • Hot water • Hair dryer

Enjoy every season at Shelter Island's peaceful Silver Beach. This beautiful home sits on a quiet street, perfect for long walks and bike rides. Only minutes' walk to Shell Beach and seconds to boat landing. During spring, summer and fall, we have 2 tandem kayaks located at the water for you to explore West Neck, Menantic and Dickerson Creeks or to take a picnic and enjoy the sunset from Shell Beach.

The space
Three bedrooms upstairs (one ensuite and one hall bath) and three down (one ensuite half bath and one full hall bath), the space is perfect for two families traveling together or a single family that likes to spread out.

Guest access
Launch our kayaks or your own watercraft at the N. Silver Beach boat landing, located seconds away at the end of the street.

Other things to note
Canine guests are considered on a case-by-case basis ($300)

Security Deposit required upon request at time of booking

Body soap • Free dryer – In unit • Hair dryer • Hangers • Cleaning products • Bed linens • Iron • Hot water • Free washer – In unit • Essentials

Welcome to Sandpoint, a Rove Travel Home!

Rove offers curated, luxury residences with the quality and care of a 5-star hotel. Properties include professionally designed furnishing, access to premium amenities, and a 24/7 Concierge team to ensure an excellent stay!

The space
Welcome to Sandpoint by Rove Travel, an exclusive Shelter Island retreat recently built on 1.4 acres, just a stone's throw from a sandy beach and across from a 12-acre preserve. This stunning home features five bedrooms, including two master suites and one room with twin beds. Sunlit and spacious, the heart of the home is a well-equipped kitchen with an oversized island overlooking a large pool and landscaped grounds. Sandpoint offers a serene 20x40 gunite pool, making it an unparalleled tranquil retreat on Shelter Island.

To finalize your reservation, all guests must pass a mandatory third-party screening process.

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Room Configuration:

Amenities:

Work From Home:

Living:

Support:

Laundry:

Pet policy:

Home Truths:

Security Deposit Policy: