Best Vacation Rentals in Shelter Island

The Pridwin is a waterfront resort located on Shelter Island with 33 well-appointed guest rooms and 16 private cottages an all-American restaurant and lively lounge with water views a full service spa-scenic pool and seasonal activities for every age The Pridwin is designed for couples, friends and families traveling together. Explore the beautiful natural setting through hiking-boating and other outdoor activities before retreating to the comfort of our private suites and cottages.

- "Loved it. Beautiful, cozy lovely." - "Beautiful gem in Shelter Island" - "One of the best hotels we’ve ever stayed in" - "Lots to enjoy in this historic and picturesque place." - "Great" - "Lovely hotel with old time feel and modern comforts." - "My siste and I had a lovely end of season trip and the Pridwin was a wonderful choice." - "Excellent, would go back again" - "LOVELY hotel, fantastic staff, and fun amenities!"

Beachfront comfort, a fitness center
Spend the day relaxing on The Pridwin Hotel's private sand beach or pampering yourself at the hotel's full-service spa.
The Pridwin Hotel offers 49 accommodations, which are accessible via exterior corridors and feature bathrobes and hair dryers. Each accommodation is individually furnished. Beds feature premium bedding. Cable television is provided.

Bathrooms include showers and complimentary toiletries. Guests can surf the web using the complimentary wireless Internet access. Housekeeping is provided daily.

Children under 13 years old are not allowed in the swimming pool without adult supervision.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "Excellent Service" - "Love it here. " - "Beautiful property and amenities " - "If you are on the fence about The Pridwin or even Shelter Island I hope this reviews tips you to book. My family and I had a fantastic stay. The property is amazing, Shelter Island is great, the amenities are top notch and the overall setting is spectacular but what made it truly special is the service. They could not have been kinder to my daughter and us. They have really outdone on making you feel welcome. "

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"

Beachfront inn with 2 restaurants and free breakfast
This smoke-free inn features 2 restaurants, a private beach, and a bar/lounge. Free continental breakfast, free WiFi in public areas, and free self parking are also provided. Other amenities include a coffee shop/cafe, coffee/tea in a common area, and a meeting room.
Bathrooms are shared.
The Rams Head Inn offers 17 air-conditioned accommodations with hair dryers and complimentary toiletries. Beds feature Frette Italian sheets and premium bedding. Guests can surf the web using the complimentary wireless Internet access. Guests have access to shared bathrooms. Bathrooms include shower/tub combinations. Housekeeping is provided daily.
A private beach and complimentary bicycles are featured at the inn.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "We loved it." - "Beautiful views and lovely service " - "It's traditional, quaint, serene, and the air is fresh" - "Historic property on a great piece of land. Out of the way in the best ways. There is a major staffing, service, training and management gap here tho. Perhaps growing pains under new ownership as everyone was trying their best and friendly, just seemed like lots of gaps and struggles. I’m loyal to the place and will return, and most lodging out east has some degree of struggle in this regard, but this was time it was very hard to get any needs met in a timely or thorough manner. "

This beachfront property offers access to free Wifi. Offering a balcony and sea views, the spacious vacation home includes 5 bedrooms, a living room, cable flat-screen TV, an equipped kitchen, and 7 bathrooms with a bath. Towels and bed linen are offered in the vacation home. The accommodation has a fireplace. Shelter Island Retreat with Outdoor Pool! offers an outdoor swimming pool, a fitness room, and a spa and wellness center that guests can take advantage of. Westerly State Airport is 52 miles from the property.

Ocean View • Other • Oceanfront • Parking • Wellness Facilities • Spa • Pool • Internet • Security/Safety • View • Guest Services • Fireplace/Heating

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.

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

Hotel in Shelter Island Heights with free breakfast and a seasonal outdoor pool
Along with a restaurant, this smoke-free hotel has a bar/lounge and a poolside bar. Free continental breakfast, free WiFi in public areas, and free self parking are also provided. Other amenities include a snack bar/deli, coffee/tea in a common area, and a seasonal outdoor pool.
Shelter Island House offers 11 air-conditioned accommodations with safes and designer toiletries. Beds feature premium bedding. Flat-screen televisions come with premium cable channels.

Bathrooms include separate bathtubs and showers and complimentary toiletries. This Shelter Island Heights hotel provides complimentary wired and wireless Internet access. Housekeeping is provided daily.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "We liked the areas for sitting outside, to sit with a coffee, talk and relax. It was convenient to have a fridge. A very different accommodation but typical for the island. We enjoyed our stay!" - "Everything was excellent. However, it would have been nice if there had been something offered for breakfast." - "Very quiet, perfect for my short getaway, so peaceful! My second floor room was tucked away and LOVED the large cushy reading chair and ottoman. A/C super quiet! Bed was very comfortable (the pillows were like baby belugas so if you prefer a flatter pillow bring one?). Enjoyed the pool once the weather cooperated, nice and secluded. Suzanne (house manager) is so nice and very accommodating. I’d love to make a return visit! "

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."

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. "

Beachfront hotel for sun and fun
At Sunset Beach Hotel , hit the beach where you can enjoy yoga, then dine onsite at the restaurant.
Change of towels is available on request.
Sunset Beach Hotel offers 20 air-conditioned accommodations with minibars and safes. Beds feature Frette Italian sheets, down comforters, and premium bedding. 47-inch Smart televisions come with digital channels and Netflix.

Bathrooms include bathtubs or showers, bathrobes, slippers, and designer toiletries. Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include hair dryers and blackout drapes/curtains. In-room massages, hypo-allergenic bedding, and irons/ironing boards can be requested. A nightly turndown service is provided and housekeeping is offered daily.

- "This is an amazingly fun place to spend a few days with lots if options to entertain yourself in beautiful surroundings. what a great team they have. be back next year. " - "Staff were great. Really an ideal location. 5 stars. " - "The location and room were great for a beach hotel. No room service and no coffee in the room The restaurant opens late and doesn’t serve breakfast. Otherwise amazing. " - "Extremely friendly staff, great place for a weekend getaway"

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!!!"

This lovely 2 bedroom, 1 bath (plus an outside shower) renovated cottage located on a large lot in the center of Shelter Island is the perfect home base for your vacation. With all the amenities of home plus beach chairs, umbrella, rafts, towels, you'll be ready for a day at the beach and relaxation at home. Each bedroom is complete with a comfortable queen size bed, ceiling fan, antique dressers, and large closets. There is a double futon in the living area. 15 X 26 cedar deck overlooking the large back yard. Close proximity to restaurants, beaches, preserve for hiking, and kayak & bike rentals.

Keywords: vacation cottage, vacation home

- "The host Kirsten was so easy to communicate with and she made my first VRBO rental experience fantastic. I spent my summers on Shelter Island as a kid and staying at her cottage brought back some great childhood memories. Already planning a trip with my adult children for next summer." - "It is a great central location on the island. Minutes from both ferries and the all-important IGA. Second time to stay at this property and we love it."

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."

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"

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.

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

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.

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

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.
.......

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

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!

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

Beautiful renovated villa with water view on Shelter Island, NY. Sleeps 6. Screened-in porch. Cable TV & WiFi. Property has pool, fitness center, and tennis. Walking distance to shops, restaurants and ferry. Available year round. Families love the bay beaches for kids. Adults love the chill vibe, restaurants and proximity to the North Fork Wineries. Great biking & hiking too. $2,000 per week June and September. $3,000 per week July and August.

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