Discover Unique Holiday Rentals in Sag Harbor, NY

Baron's Cove
Hotel
31 W. Water Street, Sag Harbor, NY, NY 11963

Featuring an on-site restaurant and seasonal saltwater swimming pool, Baron's Cove is located in Sag Harbor, New York. Free WiFi is accessible throughout the property and free private parking is available on site. Each guest room has a flat-screen cable TV and a refrigerator. The private bathrooms include bathrobes and free toiletries. Select rooms offer views of the sea or garden. Guests at Baron's Cove in Sag Harbor are greeted at the 24-hour front desk. Clothing, accessories, and refreshments are available at The Dock Shop. The dining room serves fresh American cuisine and is open daily for lunch and dinner. Breakfast and brunch are available on the weekend. Bike hire is available at this hotel and the area is popular for cycling. Mystic is 30 mi from Baron's Cove, while Montauk is 18 mi away.

Amenities:

Air Conditioner • Ocean View • Spa • Ev Charge Station • Tv • Pet Friendly • Parking • Other • View • Sports/Activities • Oceanfront • Pool

Faraway Sag Harbor
Hotel
31 West Water Street, Sag Harbor, NY, 11963, USA

Hotel in Sag Harbor with free valet parking and a fitness center
Along with a restaurant, this smoke-free hotel has a fitness center and a bar/lounge. Free WiFi in public areas and free valet parking are also provided. Other amenities include a snack bar/deli, a coffee shop/cafe, and massage/treatment rooms.
Faraway Sag Harbor offers 67 air-conditioned accommodations, which are accessible via exterior corridors and feature iPod docking stations and espresso makers. Tempur-Pedic beds feature Egyptian cotton sheets and down comforters. 48-inch flat-screen televisions come with premium cable channels and pay movies. Bathrooms include bathtubs or showers, bathrobes, designer toiletries, and complimentary toiletries.

Guests can surf the web using the complimentary wireless Internet access (speed: 100+ Mbps (good for 1–2 people or up to 6 devices)). Business-friendly amenities include safes and phones. Additionally, rooms include complimentary bottled water and hair dryers. In-room massages and hypo-allergenic bedding can be requested. A nightly turndown service is provided and housekeeping is offered daily.


Recreational amenities at the hotel include a fitness center, a seasonal outdoor pool, and complimentary bicycles.

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

Guest Reviews:

- "Nice place and very good room. " - "Very nice experience. Rooms are excellent and the facility is well kept. Dininh and entertainment options over easter weekend worked well. Bar serice was a bit hit and miss at times. That said, all the staff are very friendly and helpful." - "The hotel is stunning, they did not spare any details. The front desk team is exceptional and was helpful with everything needed. The bar is serving unique and delicious cocktails. Great location in walking distance to the Main Street restaurants and shopping. Will be staying here for all future trips out to the hamptons area. "

Villa Ebrar - Luxury with pool
Villa
16 Noyack Harbor Road, Sag Harbor, NY, NY 11963, USA

Featuring free bikes, Villa Ebrar - Luxury with pool features accommodations in Sag Harbor. The air-conditioned accommodation is 1.9 miles from Foster Memorial Beach. There's a sun terrace and guests can use free Wifi and free private parking. The villa features 4 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 3 bathrooms with slippers. A flat-screen TV and Blu-ray player, as well as a computer are offered. The accommodation has a fireplace. There is an on-site bar. Guests can enjoy the indoor pool and garden at Villa Ebrar - Luxury with pool. Montauk Point Lighthouse is 20 miles from the accommodation, while Second House Museum is 25 miles away. Long Island MacArthur Airport is 46 miles from the property, and the property offers a paid airport shuttle service.

Amenities:

Barbecue/Outdoor Cooking • Balcony/Terrace • Bar • Air Conditioner • Private Pool • Breakfast • Security/Safety • Fireplace/Heating • Oceanfront • Parking • Ocean View • Pool

Sag Harbor Inn
Hotel
45 West Water Street, Sag Harbor, NY, 11963, USA

Hotel in Sag Harbor with free breakfast and a seasonal outdoor pool
This smoke-free hotel features an outdoor pool, coffee/tea in a common area, and a seasonal outdoor pool. Free continental breakfast and free self parking are also provided. Additionally, a meeting room, a 24-hour front desk, and a lobby fireplace are onsite.
Sag Harbor Inn offers 42 air-conditioned accommodations with hair dryers and irons/ironing boards. Rooms open to balconies or patios. Flat-screen televisions come with cable channels. Bathrooms include shower/tub combinations and complimentary toiletries.

This Sag Harbor hotel provides complimentary wireless Internet access. Business-friendly amenities include desks and phones; local and long-distance calls are complimentary (restrictions may apply). Housekeeping is provided daily.


Recreational amenities at the hotel include an outdoor pool.

Guest Reviews:

- "great place to stay " - "Kind and clean " - "Great accommodations " - "Very nice" - "An outstanding property in every respect. Fabulous location, wonderful accommodations and enormously helpful staff and management. " - "Nice, but somewhat dated hotel. Clean and comfortable Plenty of onsite parking Walking distance to town Typical continental breakfast , adequate but not spectacular " - "My stay was relaxing… the place is outdated but clean and comfortable… the breakfast was minimal but it was a nice gesture… Oh! My view was amazing and the hotel is not far from shopping, eating and entertainment "

Villa Zainip - Luxury with pool
Villa
77 Northside Drive, Sag Harbor, NY, NY 11963, USA

Villa Zainip - Luxury with pool is located in Sag Harbor, just 21 miles from Montauk Point Lighthouse and 26 miles from Splish Splash. A sauna and a bicycle rental service are available for guests. There's free private parking, and the property features a paid airport shuttle service. With free Wifi, this 5-bedroom villa offers a flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The air-conditioned unit at the property features a bath and a dressing room. This villa is non-smoking and soundproof. There is an on-site bar. Guests can enjoy the outdoor swimming pool and garden at the villa. Second House Museum is 27 miles from Villa Zainip - Luxury with pool, while Hither Woods Preserve is 27 miles away. Long Island MacArthur Airport is 44 miles from the property.

Amenities:

Other • Internet • Security/Safety • Air Conditioner • Balcony/Terrace • Transportation/Shuttle • Bar • Guest Services • Wellness Facilities • Pool • View • Parking

Villa Keylime
Cottage
3, Wilson Place, Sag Harbor, NY, 11963

Located in Sag Harbor, this welcoming cottage lets you experience it all. Sag Harbor State Golf Course and Havens Beach are just a short walk away, so leave your car at the property, which offers onsite parking.

Spend a day at the nearby beach, relax by the outdoor pool, or sip a drink in the garden of this cottage, which also features a picnic area. For a change of scenery, come inside and enjoy the free WiFi, TV, DVD player, and library.

This 5-bedroom rental features a BBQ grill, firewood, luggage storage, and a safe. Bathroom amenities include a hair dryer, bathrobes, and towels. Prepare a home-cooked meal in the kitchen, complete with an oven, a stovetop, and a freezer, as well as a coffee maker, an electric kettle, and a minibar. And you won't have to pack extra clothes, because you'll also have access to laundry facilities.

Amenities:

Balcony/Terrace • Tv • Private Pool • Internet • Pool • Bedding/Linens • Kitchen • Child Friendly • Air Conditioner • Laundry

Villa KeyLime
Villa
3, Wilson Place, Sag Harbor, NY, 11963, USA

1.3 miles from Havens Beach in Sag Harbor, Villa KeyLime offers accommodations with access to an indoor pool. This beachfront property offers access to a patio, free private parking, and free Wifi. Outdoor seating is also available at the villa. With direct access to a balcony with garden views, the spacious air-conditioned villa consists of 5 bedrooms. Offering a terrace with pool views, this villa also has a cable flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 4 bathrooms with a walk-in shower and bathrobes. This villa is non-smoking and soundproof. Guests can also relax in the garden. Montauk Point Lighthouse is 14 miles from Villa KeyLime, while Second House Museum is 20 miles away. Long Island MacArthur Airport is 51 miles from the property.

Amenities:

Barbecue/Outdoor Cooking • Private Pool • Fireplace/Heating • Ocean View • Oceanfront • Other • Internet • Air Conditioner • Parking • Security/Safety • Pool • View

Historic Sag Harbor Village Gem
Apartment
Sag Harbor, New York, USA

Enjoy a private 3 room suite, tastefully decorated with soft beach colors. This 3 room suite is a King BR, separate sitting room, full bath and a fully enclosed, screened dining porch where you can enjoy drinks after a day at the beach or a stroll down Main Street. Please note: There is no kitchen.There is a microwave and apartment size refrigerator built in to the Sitting Room. VRBO does not have a category for my listing, a three room suite. Apartment is the closest. This 3 room suite with private entrance is on the first floor of my home.
There is no kitchen or laundry area.. Please continue reading for more details.

This historic home is located just 2 blocks from Main Street, in the heart of the village with restaurants, shopping, theater, dining on the Wharf plus a Hampton Jitney srop.
All the Village attractions a re within a 15 minute walk, the Wharf being the furthest.\
The newly restored iconic Sag Harbor Cinema is 5 minutes, "The Church" new art gallery and community space is 1 block on the way to Main Street, a 4 minute walk.
The Whaling Museum, the John Jermain Library, both donated by Mrs. Russell Sage, an early Sag Harbor philanthropist &, at the the time, one of the wealthiest wmen inthe US, are a 5 minute walk. There are many celebrated restaurants including the American Hotel a few minutes walk on Main Street.

Separate A/C Zone, WiFi, Microwave, Apartment Size Refrigerator.
No Kitchen or Laundry..

I provide 2 folding beach chairs, 2 portable cooler bags, 4 beach towels, a beach bag and umbrella for guests.
It is a 15 minute walk to Haven's Bay Beach and a 10 minute drive to "Long Beach" a Peconic Bay Beach.
It is a 20 minute drive to the closest ocean beach.

Guest accomodations accepted from 2 night minimum to an 8 night maximum.
Not suitable for children, no smoking, no pets.

Guest Reviews:

- "Right in town and Marla was a great host! My wife and I would definitely stay here again the next time we visit Sag Harbor." - "We loved being two blocks from town. And the suite was perfect. Marla has thought of everything. We particularly loved the free use of the sun porch. Great for picnics and morning coffee. It’s a great place to stay. Full priced but worth every penny. You feel like a local." - "Really enjoyed my stay at Marla’s! She is a wonderful and sweet host. The location is perfect if you want to visit Sag Harbor. I felt safe walking home after dinner alone. There are City Bus stops nearby that will take you to South Hampton, East Hampton, and Montauk. Easy walk from the Jitney stop. The Unit has a nook with a fridge and there is ice in the feezer which was nice to use one day. The bed was comfy, plenty of pillows, plenty of towels, great water pressure, quiet, and I felt safe. It was a wonderful stay!"

Dumar Villa by Rove - 6BR Family Home with Pool & Outdoor Spaces
House
22 Dumar Drive, Sag Harbor, NY, 11963, USA

Dumar Villa by Rove - 6BR Family Home with Pool & Outdoor Spaces is located in Sag Harbor, just 1.8 miles from Foster Memorial Beach and 20 miles from Montauk Point Lighthouse. This vacation home features air-conditioned accommodations with a patio. Outdoor seating is also available at the vacation home. With free Wifi, this 6-bedroom vacation home offers a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation has a fireplace. Guests can enjoy the outdoor swimming pool and garden at Dumar Villa by Rove - 6BR Family Home with Pool & Outdoor Spaces. Second House Museum is 26 miles from the accommodation, while Hither Woods Preserve is 26 miles away. Long Island MacArthur Airport is 45 miles from the property.

Amenities:

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

Whaling Captain Pierson's Cottage
Cottage
Sag Harbor, New York, USA

Whaling Captain Pierson's Cottage is at a waterfront property and is a unique environmental experience which is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only cottage offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as the most spectacular sunsets. (See my reviews from my other listings entitled, "Whaling Captain Pierson's Apartment" and "Whaling Captain Pierson's Apartment TOO".)

If you do not see the booking availability desired, look at my other postings of Whaling Captain's Pierson's Apartment Apartment and Whaling Captain Pierson's Apartment TOO. Or, if your party is larger than the cottage can accommodate consider booking both apartments and the cottage.

Whaling Captain Pierson's cottage is on Captain’s Row nestled behind the Captain's main house surrounded by nature overlooking the cove. The cottage’s antique furnishings reflect both a classical and whimsical ever evolving sensibility without feeling stuffy, crowded or old. The cottage has one queen size bed in the bedroom and one single size day bed in the living room, self-controlled central air cooling and heating, working fireplace, claw-foot tub/shower, kitchen, private beach access, expansive grounds and abundant parking.

The cottage is ideal for allowing privacy to loving couples, the single visitor or the various types of creative and performing artists who are looking for a haven to relax and/or create. Experience the cottage and nature or just be part of its inspiring, healing, spirit and soul uplifting surroundings.

During the day you may see ducks waddling, bunny rabbits with small white tails scurrying, blue breasted birds frolicking, turtles meandering across the lawn. Also white swan(s), ospreys, ducks or seagulls flying or swimming in Sag Harbor Cove during the day. And at dusk, deer walking through the property after nesting and napping all day.

You are free to use any of the various chairs, tables or benches situated on the front lawn and middle lawn.

Sag Harbor Cove is also where our private beach behind the property is located for water access to sun-bathing, swimming, sculling, canoeing or fishing if you rent or buy the equipment from one of the specialty shops in the Village.

I am most definitely available to give you help throughout your stay. You will be able to reach me by a cellphone call to my listed number with Homeaway/VRBO and/or email.

If you have a car or rent one, there is plenty of parking available on the street along the property.

Sag Harbor is a vibrant year-round village with plenty of activities both cultural and family oriented alike. There is a performing arts theater, gym and spas, yoga studios, art exhibits, festivals and parades which occur throughout the year. There is also a variety of antique, clothing and novelty shops as well as many fine restaurants, bars and local beaches.

Sag Harbor can be reached in 2 hours by car from New York City, the Hampton Jitney or the Long Island Rail Road. The Hampton Jitney stops in the center of the Village of Sag Harbor. The Long Island Rail Road’s Bridgehampton station is 15 minutes to and from the cottage by taxi or car.

Additionally, bicycles can be locally rented and used to explore more of Sag Harbor and other surrounding areas not necessarily within walking distances.

Guest Reviews:

- "I have now stayed here for about 8 years and always love coming here and sad to leave. Such a special place and so close to Sag Harbor that this is a dream place that can be your reality like mine" - "Stayed at the cottage for three weeks and enjoyed every minute! Great location, walk to town, and pretty view out back and sunsets. Sun shines bright through the cottage and makes it so cheerful. Owners are available and responsive. Thanks Clifton and Paris! I hope to be back!"

Entertainment Galore, Meadowood Manor by RoveTravel
House
Millstone Road 1653, Sag Harbor, NY, 11963, USA

Entertainment Galore, Meadowood Manor by RoveTravel offers accommodations in Sag Harbor, 1.8 miles from Foster Memorial Beach and 20 miles from Montauk Point Lighthouse. This vacation home provides air-conditioned accommodations with a patio. Fort Pond Bay Park is 27 miles from the vacation home and Shadmoor State Park is 27 miles away. 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. Guests can enjoy the outdoor swimming pool and garden at the vacation home. Second House Museum is 25 miles from Entertainment Galore, Meadowood Manor by RoveTravel, while Hither Woods Preserve is 26 miles from the property. Long Island MacArthur Airport is 46 miles away.

Amenities:

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

Whaling Captain Pierson's Apartment
Apartment
Sag Harbor, New York, USA

Whaling Captain Pierson's Apartment is at a waterfront property and is an apartment in one of the contributing homes which define Sag Harbor as a historic village. The house is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only house and apartment offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets. (See my other listings entitled, "Whaling Captain Pierson's Apartment TOO" and "Whaling Captain Pierson's Cottage".)

If you do not see the booking availability desired, look at my other postings of Whaling Captain's Pierson's Apartment TOO and Whaling Captain Pierson's Cottage. Or, if your party is larger than one apartment can accommodate consider booking both apartments and the cottage.

Whaling Captain Pierson's Apartment is on Captain’s Row within the main house on the second floor. The property is surrounded by nature and the apartment overlooks the cove and has views of Otter pond. The apartment’s antique furnishings reflect both a classical and whimsical ever evolving sensibility without feeling stuffy or old. This is a 1-bedroom apartment with one queen size bed. Window AC units will provide cooling during the summer and cast iron radiators provide heating in the winter. The apartment has one full bathroom. The kitchen consists of stainless steel appliances of a dishwasher, refrigerator and range with a washer and dryer right off the kitchen. The apartment has a private deck and the property a private beach, expansive grounds and parking.

The apartment allows privacy for an individual or a loving couple. It is ideal for the single visitor or other various types of creative and/or performing artists who are looking for a haven to relax and/or create. Experience the apartment’s environment or just be part of its inspiring, healing, spirit and soul uplifting surroundings.

During the day you may see ducks waddling, bunny rabbits with small white tails scurrying, orange breasted birds frolicking and turtles meander across the lawn. Also, deer can be seen nibbling the grass and white swans, ospreys, ducks or seagulls flying around or swimming in Sag Harbor Cove.

The apartment is ideal for a single visitor or allowing privacy to loving couples or the various types of creative and performing artists who are looking for a haven to relax and/or create. Experience the apartment’s environment or just be part of its inspiring, healing, spirit and soul uplifting surroundings.

During the day you may see ducks waddling, bunny rabbits with small white tails scurrying, orange breasted birds frolicking and turtles meander across the lawn. Also, deer can be seen nibbling the grass and white swan(s), ospreys, ducks or seagulls flying around or swimming in Sag Harbor Cove.

Sag Harbor is a vibrant year-round village with plenty of activities both cultural and family oriented alike. There is a movie cinema, a performing arts theater, gyms and spas, yoga studios, art exhibits, festivals and parades which occur throughout the year. There is also a variety of antique, clothing and novelty shops as well as many restaurants, bars and beaches.

Sag Harbor can be reached in 2 hours by car from New York City, the Hampton Jitney or the Long Island Rail Road. The Hampton Jitney stops in the center of the Village of Sag Harbor. The Long Island Rail Road’s Bridgehampton station is 15 minutes to and from the apartment by taxi or car.

Additionally, bicycles can be locally rented and used to explore more of Sag Harbor and other surrounding areas not necessarily within walking distances.

The apartment contains the amenities of wireless Internet access, TV, a dishwasher, microwave, coffee maker, blender, a washer and dryer, iron and ironing board and towels.

Guest Reviews:

- "We really enjoyed our stay. The small back deck had the most amazing view of Sag Harbor Cove and I could easily sit there all day watching the ospreys. Paris was an amazing host that greeted us on arrival and shared the house's history. The apartment had everything you needed if you wanted to cook there but we enjoyed the short walk into town." - "Wonderful stay. No better location! Great communication with host. If you are a cook you will need to bring some of your needed spices. The kitchen is well supplied with pots and pans. It is an electric stove as an fyi. You will enjoy your stay and have fun watching the ospreys!"

Heated Pool, Grill, Breakwater by RoveTravel
House
Franklin Avenue 71, Sag Harbor, NY, 11963

Heated Pool, Grill, Breakwater by RoveTravel is located in Sag Harbor, just a 8-minute walk from Havens Beach and 15 miles from Montauk Point Lighthouse. This vacation home provides air-conditioned accommodations with a patio. Second House Museum is 20 miles from the vacation home and Hither Woods Preserve is 21 miles away. With free Wifi, this 3-bedroom vacation home features a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are available in the vacation home. For added privacy, the accommodation features a private entrance. Guests can enjoy the outdoor swimming pool and garden at the vacation home. Fort Pond Bay Park is 22 miles from Heated Pool, Grill, Breakwater by RoveTravel, while Shadmoor State Park is 22 miles from the property. Long Island MacArthur Airport is 50 miles away.

Amenities:

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

Whaling Captain Pierson's Apartment TOO
Apartment
Sag Harbor, New York, USA

Whaling Captain Pierson's Apartment is at a waterfront property and is an apartment in one of the contributing homes which define Sag Harbor as a historic village. The house is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only house and apartment offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets.(See my other listings entitled, "Whaling Captain Pierson's Apartment" and "Whaling Captain Pierson's Cottage".)

If you do not see the booking availability desired, look at my other postings of Whaling Captain's Pierson's Apartment and Whaling Captain Pierson's Cottage. Or, if your party is larger than one apartment can accommodate consider booking both apartments and the cottage.

Whaling Captain Pierson's Apartment Too is on Captain’s Row within the main house. The property is surrounded by nature and the apartment overlooks the cove and has views of Otter pond. Whaling Captain Pierson's Apartment Too is a first floor completely private apartment of which nothing is shared other than the hallway of the main house. Once inside of Whaling Captain Pierson's Apartment Too no one enters or exits but those guests of your party.

Whaling Captain Pierson's Apartment Too’s antique furnishings reflect both a classical and whimsical ever evolving sensibility without feeling stuffy or old. The kitchen consists of stainless steel appliances. The kitchen is fully outfitted with plates, silverware, stainless steel pots and pans, cups, saucers, salad bowls, coffee maker, coffee press, food processors, toaster, toaster oven, basic condiments, sugar, sugar substitutes, coffee, etc. The apartment is a two-bedroom apartment which has one queen size bed in the master bedroom and one double size bed in the second bedroom. Additionally, the day bed in the living room is a single bed that can sleep one person. Window AC units will provide cooling during the summer in both bedrooms and cast iron radiators provide heating in the winter. The apartment has a full bathroom with a washer and dryer right off the bathroom. The apartment has a private deck and private sun porch. The apartment guests have welcomed access to the property’s private beach, expansive grounds and parking.

Common amenities are TV, Cable TV, and Wireless Internet with laptop friendly workspaces.

The Apartment is ideal for allowing privacy to loving couples, the single visitor or the various types of creative and performing artists who are looking for a haven to relax and/or create. Experience the Apartment’s environment or just be part of its inspiring, healing, spirit and soul uplifting surroundings.

During the day you may see ducks waddling, bunny rabbits with small white tails scurrying, orange breasted birds frolicking and turtles meander across the lawn. Also, deer can be seen nibbling the grass and white swan(s), ospreys, ducks or seagulls flying around or swimming in Sag Harbor Cove.

Guests should feel free to use any of the various chairs, tables or benches situated on the front porch, the front lawn and the grounds.

Sag Harbor Cove is where my private beach behind the property is located for water access to sun-bathing, sculling, canoeing or fishing if you rent or buy the equipment from one of the specialty shops in the Village.

Bicycles can be locally rented and used to explore more of Sag Harbor and other surrounding areas not within walking distance.

Long Wharf beach, Long Beach and Haven’s Beach are 3 public beaches in relative close proximity to the house. Long Wharf beach is in the center of the Village of Sag Harbor within the 7 minutes walking distance from the house. However, the other two beaches are within a comfortable bicycling distance from the house rather than by car. One would need a car’s parking pass obtained from Sag Harbor’s municipal building to be able to take one’s car to the beach for beach parking. Only a limited number of car parking passes are available in the Village per season.

Guests can always text, email or call me with any questions, concerns or just for places to go and/or visit during or after their stay.

Breakfast, lunch and dinner can be obtained from the Cove Deli which is just across the street from the house/apartment.

Sag Harbor is a vibrant year-round village with plenty of activities both cultural and family oriented alike. There is a performing arts theater, gyms and spas, yoga studios, art exhibits, festivals and parades which occur throughout the year. There is also a variety of antique, clothing and novelty shops as well as many restaurants, bars and beaches.

Sag Harbor can be reached in 2 hours by car from New York City, the Hampton Jitney or the Long Island Rail Road. The Hampton Jitney stops in the center of the Village of Sag Harbor. The Long Island Rail Road’s Bridgehampton station is 15 minutes to and from the Apartment by taxi or car.

If you have a car or rent one, there is plenty of parking available on the street along the property.

Guest Reviews:

- "My elderly mother, my two cats (who have never traveled), and I all had such a relaxing, refreshing, and incredible experience thanks to Paris and Clifton’s attentiveness to detail and welcoming spirit. The house was more than expected when we arrived. The photos on here are fantastic and thorough, but they don’t really show how close to the water you are which was the best surprise! The view, particularly from the screened sunroom, kitchen, and deck, is breathtakingly serene. It, along with the beautiful, historic home filled with so many charming antiques and interesting details, matched with Paris’ warm welcome and telling us of the history of the home all immediately immerse you in the spirit of Sag Harbor. We had only traveled one hour east to come here, but it felt like we had been transported hundreds of miles away. And the best part was that the 2 cats also loved it! They specifically enjoyed the screened sunroom. It was such a relief to be able to bring them with us and Paris and Clifton were so easygoing and inviting towards them and us which enabled us to truly relax. I did make sure to “cat proof” the home when we arrived (I brought my own bedding, put away anything I thought they could break, and covered any upholstered furniture with throw blankets), but that was all my doing as I wanted to be a considerate guest, having brought my pets with me. I really can’t say enough good things about this home. The location is ideal. It’s right on the cove with a large piece of beautiful property and still only a few minutes from all the shops and restaurants down on Main Street in Sag Harbor. We had only two days of sunshine while there and two cloudy days, but the sunsets on the water on the sunny days were unmatched to any I’ve ever seen and we enjoyed them directly from the screened sunroom in our beyond immaculate and spacious apartment. This place is perfect for any person of any age (my mother has a slightly hard time walking and the very few steps she had to navigate were not a problem, which was a big relief)! It was stocked with just about any item you can imagine, especially the gorgeous kitchen, and the attention to the small details - even the antique toilet paper holder and the fantastic smelling sachet bag in the bedroom closet - made this place a warm, gorgeous, and very comfortable place to stay, all thanks to Paris and Clifton. I would stay here again, no question, and you should as well!"

Coves Bay Beauty
House
Sag Harbor, NY, USA

Located in Sag Harbor in the New York State region, Coves Bay Beauty features a patio. This property offers a private pool, free WiFi and free private parking. The air-conditioned holiday home is composed of 5 separate bedrooms, a fully equipped kitchen with a microwave and a toaster, and 4 bathrooms. A TV is provided. Foster Memorial Beach is less than 1 km from the holiday home, while Montauk Point Lighthouse is 26 km away. The nearest airport is Long Island MacArthur Airport, 79 km from Coves Bay Beauty.

Amenities:

Laundry • Internet • Child Friendly • Pool • Wheelchair Accessible • Parking

Perfect Summer Retreat in Sag Harbor - Walk to Beach
House
Sag Harbor, New York, USA

A great place for a short or long-term vacation, this beautiful, 2-bedroom, 2-bath ranch home is located in a quiet neighborhood just blocks from the beach and a short 5-minute drive or 2-mile bike ride to Sag Harbor Village.

The home features an open floor plan, hardwood flooring, fireplace, air conditioning, flat screen TVs, and a fully equipped kitchen with stainless steel appliances. Stroll through French doors to enjoy barbecues on the patio (gas grill provided) and relax in the large private yard. Newly renovated basement provides additional entertainment including a dart board and playing pool or air hockey. We also provide complimentary use of an EV charger outlet for renters with electric vehicles (must bring own plug-in charger). With a sofa bed in the living room and a futon in the den, this home can sleep up to 8 guests. A perfect summer retreat in an ideal location.

Requests for weekend-only rentals during the summer are considered based on availability.

Our rates are negotiable.

Guest Reviews:

- " Absolutely wonderful!" - "Great" - "Very clean, tidy and comfortable in a cute neighborhood." - "Excellent location, easy access to a bay beach. Beautiful home, lots of games and things to do as a family in the house, with a comfortable backyard. Ruby was very responsive to questions and the home was spotless and well appointed. Highly recommend!" - "We were very impressed with the property. Besides its cleanliness and nicely appointed decor. It had a large and secluded backyard and a large semi finished basement with a pool table! The location was in a wonderful neighborhood close to beaches and shopping! Highly recommend!"

Villa Kimaal - Luxury with pool
Villa
33 Carroll Street, Sag Harbor, NY, NY 11963, USA

Providing a bar, Villa Kimaal - Luxury with pool offers accommodations in Sag Harbor. This property offers a private pool and free private parking. The property offers car rental and features a garden and picnic area. With free Wifi, this 5-bedroom villa provides a cable flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Featuring air conditioning, this unit has a dressing room and a fireplace. For added privacy, the accommodation has a private entrance and is protected by full-day security. Guests can also relax in the shared lounge area. Havens Beach is 1.7 miles from the villa, while Montauk Point Lighthouse is 16 miles away. Long Island MacArthur Airport is 48 miles from the property.

Amenities:

Air Conditioner • Parking • Security/Safety • Kitchen • Tv • Other • Bar • Barbecue/Outdoor Cooking • Transportation/Shuttle • Breakfast • Pool • Entertainment

COTTAGE IS AVAILABLE for FALL& WINTER STAYS
Cottage
sag harbor, New York, USA

Spacious ,adorable ,well maintained,private cottage with own driveway,separate from main house . Outdoors has 2 patios, one covered,with relaxing lounge chairs,other patio has dining table, ,propane fire pit, gas grill .Downstairs Interior has spacious full kitchen w/stainless appliances, full size washer/dryer,dining table seats four or more with extension. Living space has queen sleeper couch, working desk, flatscreen smart TV. Upstairs includes, large bedroom with king-bed plus plenty of room for a child's crib .Bathroom has slate floor ,tile shower w/glass doors all new fixtures . House is fully AC & heated with duel zone.
Peaceful surroundings ; Nature trails for walking and biking literally across the street from the Nature Perserve yet 1 mile to Village Center or Ocean Beaches. Plenty of restaurants with outdoor dininig, shopping, boating, & antiquing. Don't miss Saturday morning Farmers Market!. Sagharbor is a great sailing community! Plus it's only 5 miles to our Fabulous Ocean Beaches (one of the closest neighborhoods in Sagharbor to the Ocean).Great location to get to Bridgehampton and East Hampton without getting on Montauk hwy. An easy ferry ride to Shelter Island or the North Fork for wine tasting or Wolfers Winery just down the road ! .THE HAMPTON CLASSIC HORSE SHOW in Bridgehampton is a quick 7 min drive or to The HAMPTON FILM FESTIVAL in Easthampton. Fall Foliage ,Pumpkin/Apple Picking and Wine Tasting Tours (2 1/2 miles from Wolfers Vineyard. HARBOR-FEST(Sept) MUSIC-FEST (Oct).There are also winter holiday venues. Come to the HARBOR FROST FESTIVAL for the cold weather lovers! Did I mention ice sculptures?..Sagharbor is a picture postcard village all year round ! You won't want to miss the sunsets from Long Beach or a stroll on the Long Wharf. A perfect getaway holiday location for couples or small families!

Guest Reviews:

- "Lovely stay here. Very clean and cute. Just what we were looking for. Thank you for hosting!" - "property was a perfect fit for our month long stay. joanne, the owner, was extremely responsive to all our needs and made our stay a pleasant experience. cottage is in great condition, will be happy to stay again! " - "Perfect from beginning to end. Everything needed was available. Joanne is the hostess with the mostest!!! I hope to visit this lovely cottage again."

Sag Harbor Inn
Hotel
45 West Water Street, Sag Harbor, NY, NY 11963, USA

Located in Sag Harbor, within 15 miles of Montauk Point Lighthouse and 21 miles of Second House Museum, Sag Harbor Inn has accommodations with a shared lounge as well as free private parking for guests who drive. Featuring a seasonal outdoor swimming pool, the 3-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. The property provides a 24-hour front desk, and luggage storage for guests. The rooms are equipped with a desk and a flat-screen TV, and some rooms at the hotel have a terrace. All rooms will provide guests with a fridge. A continental breakfast is available at Sag Harbor Inn. Hither Woods Preserve is 21 miles from the accommodation, while Fort Pond Bay Park is 23 miles from the property. Long Island MacArthur Airport is 50 miles away.

Amenities:

Wellness Facilities • Business Services • Entertainment • Parking • Smoking • Oceanfront • Accessibility • View • Balcony/Terrace • Guest Services • Security/Safety • Internet

Sag Harbor Charmer - 2 Bedroom Cottage; Walk to Town
Cottage
Sag Harbor, New York, USA

Beech Tree Cottage is a charming, fully-furnished two-story cottage in the picturesque village of Sag Harbor, NY (the Hamptons). The cottage is located in a quiet, historic neighborhood, walking distance to town. It's an easy 5-minute walk along the waterfront to Sag Harbor's Main Street, and a short drive to the beach.

We are year-round residents who live next door. The cottage has its own private entrance and off-street parking. The back deck has a bistro table and chairs for outdoor dining, and is trellis-screened for privacy. The two bedrooms upstairs have a queen size bed and two twins, all with memory foam mattress toppers. Linens and towels are provided. The lounge and kitchen/dining area is decorated in nautical/beach style, with white slipcovers and English pine furniture. Other features include a cast iron fireplace stove (gas), wireless internet access, flat-screen TV, VCR/DVD, & many books and games. The kitchen is fully equipped with dishware, pots and pans, coffee maker, microwave, etc. Accommodates 4 people, maximum.

PLEASE NOTE:
- Access to the bedrooms is via narrow spiral staircase, which is unsuitable for the elderly or infirm, as well as very young children or babes in arms. We cannot allow any children under 5 years old.

- The bathroom is downstairs; bedrooms are upstairs.

- We regret we are unable to provide beach passes, but you can purchase day passes at the beaches themselves.

- We do not allow pets, no matter how small, well-behaved, or non-shedding.

- During peak season (Memorial Day - Labor Day), we cannot accommodate early check-ins or late checkouts. Unapproved early check-ins or late checkouts will be subject to an additional fee. At other times of the year, early checkins and late checkouts can only be accommodated subject to availability and prior approval. Thank you for understanding.

Guest Reviews:

- "The cottage was great, peaceful, quiet, owners were kind and helpful. Everything was as-expected from the photos and description on the site." - "Clean cozy place with a great location. As advertised." - "Cute rustic cottage 5 mins walk from down town Sag Harbor." - "We had an amazing stay in the cottage. Wonderful location which is super close to downtown Sag Harbor. The neighborhood was lovely, quiet, and walkable. Nothing like waking up in the morning and strolling into town for breakfast and the local farmer's market. The cottage was clean, beautifully decorated, and had everything we needed for our stay. Thank you to our gracious hosts. We would 100% recommend."

queeen room
House

Queeen room, a property with a garden and a terrace, is located in Sag Harbor, 25 km from Montauk Point Lighthouse, 34 km from Second House Museum, as well as 34 km from Hither Woods Preserve. The air-conditioned accommodation is 2 km from Havens Beach, and guests benefit from complimentary WiFi and private parking available on site. Towels and bed linen are provided in this accommodation. The homestay offers a buffet or vegetarian breakfast. Fort Pond Bay Park is 36 km from queeen room, while Shadmoor State Park is 37 km away. The nearest airport is Long Island MacArthur Airport, 80 km from the accommodation.

Amenities:

Air Conditioner • Internet • Balcony/Terrace • Child Friendly • Ocean View • Oceanfront • View • Private Beach • Parking

The Cooper-Burke House
House
Sag Harbor, New York, USA

The Cooper-Burke House is located in the heart of Sag Harbor's historic district. The house, built in 1810 was first the site of William Cooper's Whale Boat Enterprise. Afterwards, the house became the first Catholic Meeting House in Suffolk County formed by Michael Burke in 1826.

As in my other 3 VRBO offerings, this house's antique furnishings reflect both a classical and whimsical ever evolving sensibility without feeling stuffy or old. Each area of the house offers the opportunity to relax reading a book or writing or even watching television. There is an outside deck with table and chairs to do so as well. WiFi is throughout the rooms of the house and reaches the outside deck as well. A security camera system with posted signs monitors the outside surrounding grounds for added security, important if children are outside playing in the yard. The guests are free to access all main floor's areas as well as the entire grounds.

Many Main Street restaurants such as the American Hotel, Lulu's, Paige, Wolffer Kitchen, Sen, Sag Pizza and Goldberg's, etc are a few minutes away. Also, the Dockside restaurant is by the water on Bay Street. On Main Street one finds the Sag Harbor Cinema, The Bay Street Theater, Schiavoni's Market and Yoga Shanti. The house is a 12-minute walk to Haven's Beach. 1-minute around the corner from the house is Cavaniola's Wine, Cheese and Kitchen shops as well as the Sag Harbor Beverage store.

The house is a 3 minutes walk to Main Street for both the Hampton Jitney and/or Ambassador pickup and drop-off bus stops.

Lastly, bicycles can be locally rented and used to explore more of Sag Harbor and other surrounding areas not necessarily within walking distances.

Guest Reviews:

- "The home had everything we needed, including firefly show at dusk. Paris and Clifton were attentive hosts." - "This is an interesting house…we appreciated the vintage/industrial pieces. The only negative is the bathroom. Very samall and the tub with shower is awkward to get into and to adjust the water . Towels need replacing..they are scratchy. Paris helped with a toilet problem and filled us in on the history. We’d come back again but would bring our own towels."

best view
Bed & Breakfast

Offering a garden and sea view, best view is set in Sag Harbor, 25 km from Montauk Point Lighthouse and 34 km from Second House Museum. The air-conditioned accommodation is 2 km from Havens Beach, and guests benefit from complimentary WiFi and private parking available on site. Towels and bed linen are featured. The bed and breakfast offers a buffet or vegetarian breakfast. A terrace is available for guests at best view to use. Hither Woods Preserve is 34 km from the accommodation, while Fort Pond Bay Park is 36 km away. The nearest airport is Long Island MacArthur Airport, 80 km from best view.

Amenities:

Balcony/Terrace • Air Conditioner • Parking • Internet

Room 1 queen bed on waterfront + bikes and kayaks
Bed & Breakfast
Sag Harbor, New York, USA

Historic waterfront home in historic Sag Harbor.
Walking distance to restaurants and shops.
free Bikes and kayaks. Large room with queen bed and pullout sofa. The hosts will tell you all there is to do in the area.

Guest Reviews:

- "I was there with my adult daughter. The hosts could NOT have been nicer! They gave us lots of tips on local places and supplied us with tons of food in the am! They also do boat cruises around the harbor. We took one which was super fun. Anton- the host - pointed out boats owned by Hollywood stars and famous musicians. We will definitely be back!" - "Inn and innkeepers were wonderful--thank you!" - "Anton and Linley were great hosts and their home was a wonderful place to stay. It is a short walk from downtown. Our room was clean and comfortable. The view from the back porch was beautiful and peaceful with a lovely view of the water. A very gracious accommodation. We will be back!"

Bohemian chíc 2 bedroom home w/indoor pool & sauna in Sag Harbor.
House
Sag Harbor, New York, USA

This is a very special property with a beautiful and private indoor pool, sauna, and hot tub. It’s perfect for honeymoons, anniversaries, and romantic getaways, but can also accommodate small groups and families.

There is access to massage, yoga, sound and water therapy upon request. As a guest, you can choose to have privacy, or schedule a day of healthy and healing activities including:

-
- group surf or paddle board excursions
- water or traditional massage therapy, harmonyum healing, Reiki
- Pulsed electromagnetic field therapy

Let’s talk about how you would like to feel during and after your visit, and we will help you get there.

Bruce

Guest Reviews:

- "Upon check in we met our host. He was kind and informative. The area is clean, location near Circle Beach. The home was beautiful eclectic and comfortable. Sadly we were only there for a weekend but will definitely book this home again. Wonderful. Excellent. Thank you Bruce for such a great weekend home! " - "Loved our stay! House is very comfortable and is in a peaceful neighborhood. Short drive to town and close to a dog beach, we will be back next Summer!"

Romantic Studio Cottage, Walk to Town
Apartment
Sag Harbor, New York, USA

A romantic hideaway in Sag Harbor's historic district, within easy walking distance of Main Street. This sweet studio guesthouse is perfect for two, with its own private entrance. In addition to the studio living space, it features a well-stocked kitchenette, full bathroom (shower only), cozy electric fireplace, and comfy queen-size Murphy bed. Free WiFi included.

Available for weekends stays only.

Please note that parking is available for ONE car only, and is street-side, just past the cottage. No driveway parking is available.

During peak season (Memorial Day - Labor Day), we cannot accommodate early check-ins or late checkouts. Unapproved early check-ins or late checkouts will be subject to an additional fee. Thank you for understanding.

Please note we cannot provide beach passes, as they are non-transferable. Day passes can be purchased at the local beaches.

Please review our house rules and rental agreement before requesting a booking. Thank you.

Guest Reviews:

- "This cottage is an absolute dream. Full of light and so well decorated. It was in the perfect location. Check in couldn’t haven’t been easier. The place was very clean and very comfortable. Highly recommend and would love to stay again." - "We loved our stay in the cottage. It was adorable! The location was perfect too! The hosts were great and very helpful as we had never been to Sag Harbor before. I hope we can come back again someday."

Room3, best waterfront view +shared bath, bikes+kayaks
Bed & Breakfast
Sag Harbor, New York, USA

Charming room with shared bath in the heart of the historic village.
Free bikes and kayaks and a healthy breakfast.
The hosts will share all their recommendations for restaurants and the best beaches.

Guest Reviews:

- "Charming, comfortable stay. Amazing location and wonderful hosts! Would stay again and look forward to it." - "Absolutely loved staying here. What a charming and inviting Home. Linley and Anton had just the right touch in being helpful and providing good information about things to do. The room was cozy and the breakfast was healthy. It was a close walk to town and Sag Harbor was definitely the place to be." - "Best VRBO owners I have ever met I felt right at home the minute we connected and throughout the process I felt like I was with guests who all felt United in sharing the day Short stay but definitely recommend it if u want to explore Sag Harbor I will b back"

Secluded Hamptons Cottage
House
Sag Harbor, New York, USA

Your private getaway, perfect for the Hampton Classic. Ample parking for trailers. Bright airy cottage high up in the trees. High ceilings, open floor plan. Wrap around deck. Partly sunny, part covered. Totally private. On flag lot in the woods. Natural, unaltered landscape attracts wildlife for viewing.
Lovingly described as “adult tree house.”

Guest Reviews:

- "Unique and very comfortable layout." - "The location was perfect for us, close to other family members we vacation with each year. The whole experience was enjoyable!" - "Colleen’s cottage is the perfect place for a relaxing getaway. The wrap around porch amongst the trees was so calming. It is a great location, equally as close to Sag Harbor and Southampton town, plus all the quaint local restaurants on Noyac Rd. Highly recommend!"

Sabbatical a Private guest cottage in Sag Harbor
Cottage
Sag Harbor, New York, USA

Welcome to Sabbatical a private guest cottage with full amenities.

Sabbatical sits on 3 acres of property. Access to walking trails steps from cottage. Enjoy a short walk to bay beaches. World Class golfing is close by.

Sag Harbor village is 4 miles from Sabbatical and has many charming stores, restaurants and theaters.

Come stay and enjoy Your Sabbatical

Guest Reviews:

- "Susan was very nice and attentive to our group and the stay was clean and nice. We would recommend this property" - "Clean, comfortable and exactly as advertised. Lovely little guest cottage on a very quiet street. Easy from start to finish" - "Great location! Susan is very responsive, helpful and a wonderful host! My friend and I were here on a work trip. Being at the Sabbatical quickly felt like home and was very comforting to come home to after a long work day. We were very pleased with our stay! I loved the very peaceful side yard with a grill and a magical place for morning coffee!"

Island View Manor-Secluded, Pool Hot, Tub
House
Sag Harbor, New York, USA

*Families Only*
No Bachelorettes/ Bachelor parties. No Girls/ Guys weekends. No large unrelated groups.

5 Bedrooms, 3 full bathrooms
- Master bedroom: king bed, ensuite bathroom, couch, double-armoire, smart TV, and bedside tables, lights, and plug-ins

- Bedroom 2: king bed, smart TV, desk, walk-in closet, bedside tables, lights, and plug-ins

- Bedroom 3: king bed, smart TV, closet, bedside tables, lights, and plug-ins

- Bedroom 4: queen bed, smart TV, desk closet, bedside tables, lights and plug-ins

- Bedroom 5: 2 king beds, ensuite bathroom, smart TV, and bedside tables, lights and plug-ins

- Kitchen: new stainless steel appliances and fully stocked kitchen for the serious chef, breakfast noon, and plentiful cabinet storage including a pantry

- Living room: large sectional sofa and Eams lounge chair with seating for 12, wood-burning fireplace, large smart-TV screen TV, long coffee table

- Dining room: long banquet-style table with seating for up to 12, chandelier, soft adjustable lighting for cozy meals

- Bathroom 1: full bath with shower, bathtub, and heated floors

- Bathroom 2: full bath with shower

- Bathroom 3: full bath with tub/ shower combo

- Laundry room: washer and dryer

Exterior details

- Garden: Secluded backyard surrounded by mature oak forest with extensive terraced landscaping

- Pool: fully automated, modern 40 foot long heated saltwater pool

- Hot tub: accommodates up to six

- Chaise lounges: 5 adjustable CB2 chaise lounge chairs with umbrellas and side tables perfect for sunbathing or lounging in the shade

- Banquet table: modern farmhouse style wood banquet table with seating for 8 under 10 ft umbrella

- Cafe table: small cafe style two-top table to enjoy a morning coffee or work by the pool

- Lounge seating: plush hotel-style lounge seating with seating for 10 around a large wood burning fire pit adjacent to the hot tub

- Outdoor grill: Webber propane Spirit 2 grill

Town of Southampton Rental Permit : RP220368

Island View Manor is a newly renovated country retreat in the heart of the Hamptons, five minutes from the Village of Sag Harbor and a short walk to beautiful Long Beach. The private home has a 40 ft heated salt-water pool and hot tub surrounded by a lush, terraced garden and mature oak trees. The pool is set on an expansive patio with resort-style chaise-lounge chairs and umbrellas, a shaded outdoor dining table, a gas Webber grill, and a fire pit with plush lounge seating.

Island View Manor is a summer dream. Soak up the sun or relax in the shade next to the large, heated salt-water pool, perfect for a refreshing dip or swimming laps. Enjoy grilling fresh fish and lobster from the bay on the propane Webber grill and serving it up to friends and family on the outdoor banquette table, which includes a 10-foot umbrella for all those afternoon BBQs. In the evening, turn on the bistro lights, slip into the hot tub for a soak, and dry off around a cozy fire at our outdoor lounge centered around a large wood-burning fire pit. The perfect summer day.

Designed as a relaxing country retreat, the home has warm white walls and large windows throughout providing abundant natural light and beautiful views of the surrounding forest and bay. Its original white oak flooring, dimmable lighting, and high-quality furnishing will help ensure your comfort. The home includes a fully equipped chef’s kitchen ideal for entertaining or extended stays. Tasteful Hampton’s inspired art and decor throughout help create an authentic sense of place.

Each bedroom is designed with hotel-quality bedding (SweetNight mattresses and pillows) and considerate touches including smart TVs, luggage racks, and bedside tables with easily accessible lighting and plug-ins. The master bedroom has a couch for daytime lounging, while two other bedrooms have desks for the remote worker. We’ve upgraded fixtures and included stainless steel appliances throughout the home.

The living room features an Eams Lounger and Floyd sectional couch centered around a functioning wood-burning fireplace perfect for cozy fall, winter, and spring nights. The home also has a classic formal dining room perfect for dinner parties and holiday gatherings. Seating in both the living and dining rooms can easily accommodate a full house.

Island View Manor is ideally located in the heart of the Hamptons. The home is a 20-minute walk or 5-minute drive to Long Beach, and an 8-minute drive to the incredibly charming historical Village of Sag Harbor, which has wonderful restaurants, shopping, and amenities (see our guest book for recommendations).

The house is just 10 minutes to Bridge Hampton, 20 minutes to both Southampton and Easthampton, and 40 minutes to Montauk at the far eastern end of Long Island. It's a mere 5 minutes to the Shelter Island Ferry, offering easy access to the island and the North Fork, the perfect afternoon trip.

The Hamlet to Hamlet footpath -- a hiking trail that links the various towns and villages around the Hamptons -- is easily accessible at the top of our street, providing bucolic hiking through the countryside and excellent trail running.

Guest Reviews:

- "We booked this home for my large family traveling in for my son's wedding. The home was perfect for everyone. The backyard area with the pool was a favorite of everyone. The set up was perfect. There was a large table for those that wanted to eat outside. Lounge chairs for conversations and relaxation. There was also a Jacuzzi. The living room was large with a nice large sectional. This was also a great gathering place. The property managers were very attentive. Thank you all so much for providing a beautiful home where wonderful memories were made..."

Charming Sag Harbor Cottage by the Beach!
House
Sag Harbor, New York, USA

Gorgeous 2 bedroom, 1 bath cottage a stones throw away from Long Beach in Sag Harbor. Perhaps the greatest (definitely the most charming) village in The Hamptons, Sag Harbor is just a 5 minute drive (or bike ride) away!
Enjoy breakfast on the patio, walk down to the beach for the afternoon, and grab drinks and dinner in town.

Guest Reviews:

- "Cottage is lovely. I’ve stayed in many VRBOs over the years and this one rose above the rest in terms of responsiveness by owner (Greg) and the amenities. Little things like providing charger cords and Nespresso pods. Outside space is lovely. Spent every morning out there. Proximity to town (5 minute drive) and the beach is great. Beach is two minute walk. We will definitely be back!" - "Our family stayed here for 3 nights and really enjoyed the cottage and the area. There was everything needed at the cottage. It was beautiful"

Stay & Dine
Cottage
Sag Harbor, New York, USA

Stay at our quaint cottage & treat yourself to a Sag Harbor experience. A two minute walk to a private beach on the bay.

Included in price:

$250 gift certificate for the restaurant of your choosing.
Welcome gifts: local wine, cheese & fruit platter, assorted chocolates, ...

*After Labor Day 2023 - 14 night min.*

Enjoy the heart of the Hamptons in beautiful Sag Harbor with all that it has to offer, from shopping to a variety of restaurants. This is a charming cottage with a quick walk to Main Street, Sag Harbor. Located in a private community with a gorgeous, private beach. Offering limited waterfront views from the front yard and 2 minute walk to the scenic sandy bay beach that is ideal for a family with young children or for two couples. Cooled by the bay breeze, the home also offers window unit air conditioners. The yard offers shade trees and an outdoor grill. Walk home from the beach to grill lunch or grab a cool drink.

Guest Reviews:

- "The house is great value for money, amazing location, private beach is less than minute walk, very calm and vice area, house is very clean and has everything you might need. We have really enjoyed the stay and Michael is a fantastic host! I would really recommend that to everyone, very fair value for money!" - "The cottage was comfortable and a convenient location for us. Michael and his wife were very communicative and helpful. The internet and TV were a plus as well. If we need a place in Sag Harbor again we will definitely consider this location."

Sabbatical a Private guest cottage in Sag Harbor
Cottage
Sag Harbor, New York, USA

Welcome to Sabbatical a private guest cottage with full amenities.

Sabbatical sits on 3 acres of property. Access to walking trails steps from cottage. Enjoy a short walk to bay beaches. World Class golfing is close by.

Sag Harbor village is 4 miles from Sabbatical and has many charming stores, restaurants and theaters.

Come stay and enjoy Your Sabbatical

Guest Reviews:

- "Beautiful studio apartment and truly a retreat from our busy work schedules. Nice response from host when we had questions. Lovely location and truly inspiring..." - "This cottage was absolutely perfect My husband and I stayed with our 2 month old baby and it couldn’t have been more perfect. Susan was incredibly accommodating and welcoming and the cottage was stocked with everything we needed. It was clean, quiet and close to town. Overall a perfect weekend away."

sunset bikes and kayaks in the village
Bed & Breakfast
Sag Harbor, New York, USA

Charming location within walking distance of the shops and restaurants.
Helpful hosts with local knowledge.
Your host, the captain is available for the best boat charters in Sag Harbor.
Fully air conditioned.

Guest Reviews:

- "Loved my stay on many levels. The hosts were nothing short of welcoming with a warm smile and home. The view, spectacular. if you're looking for the four seasons, this is not the right fit. You are basically a guest in a wonderful home that gives you the truest feel of what it is like to live in the Hamptons. Flowers, Birds, Peace, Quiet, Calm, Water view, kayaks, repeat! Town is .5 mile away and easily accessible. I can't wait to go back."

Authentic Sag harbor post and beam
House
Sag Harbor, New York, USA

New 2 bed 3 bath home offers 2 master suites, jacuzzi tub, smart TVs, central air, and a hot tub. This unique property resembles a mother daughter style property- two houses, separated by a 40ft breezeway/courtyard. This listing is for one of the two houses- contact owner if interested in second home. The owner is a local contractor/property manager- built to the highest standards; meticulously maintained. Personal concierge available for fishing, kayaking, surfing, boating, yoga, massage.

Guest Reviews:

- "It was the perfect spot for our group. The hosts were wonderful and had coffee, water, towels and everything all stocked for us. The house had everything we needed."

Tranquil getaway just steps from Long Pond Trails and Sag Harbor Village.
House
Sag Harbor, New York, USA

This lovely one bedroom Lily Pond home is situated on nearly one private acre enabling you to enjoy the calm zen-like atmosphere among mature whispering trees, beautiful east end light and water view all day long.
Entire Home rental includes the added benefit of a separate Walpole built studio on the property; a perfect space for quiet contemplation, meditation or a long lovely nap!
Walk to Estia's Little Kitchen, hike the Long Pond Nature Trail, enjoy Topping Rose in Bridgehampton down the road or Wolffer Vineyards nearby.
Sag Harbor Village is a minute up the road.
The location affords the best of both worlds - a dynamic chic one-of-a-kind vintage village nearby and a quiet place to rest your soul.
Real wood floors, soaring ceilings, natural light, water views add to a creative relaxed vibe.

Guest Reviews:

- "Everything was perfect, thank you so much!"

Sag Harbor Enchanting Home near to Sandy Beach
House
Sag Harbor, New York, USA

A 2 bedroom enchanted garden home with a private bay beach just a few yards away. In a quiet beach community, a bike ride or walk on the beach to the old whaling town of village of Sag Harbor. A hidden paradise in the Hamptons.

Guest Reviews:

- "We booked this oasis sight unseen. We don't want to leave. Completely up to date, pristine, large property, linens and beach towels. Best part - steps away from the private beach in Ninevah. Thank you Kevin. We will be back."

Bayfront Sag Harbor ! Sunsets ! Dock and Mooring ! Avail for July 2024 ! n
House
Sag Harbor, New York, USA

Two bedroom two bath waterfront home in Sag Harbor . Available for Summer 2024! Watch the ducks every morning while drinking your coffee. on covered porch ... Enjoy happy hour on you own private dock ! Steps to Serene Green .Walk to Long Beach ! Bike to Sag town ! Outdoor shower / new BBQ gas grill ! Kayak , paddle and boat right off your private floating dock !
Sleeps four but have two full air mattresses for guest sleepover .Newly renovated bathroom ! TV / wifi in every room .Peloton. Best sunsets around ! No pets ! Boat Mooring on floating DOCK ( NEW)

Guest Reviews:

- "We loved this house. From all blue and white decor to spectacular views of water and wildlife it was just right for relaxing. The covered open air porch added to our experience. The house is the last one on the block with lots of surrounding foliage so it has a secluded feeling. The host was very responsive and helpful. Would highly recommend this property for a couple or family of four."

Peaceful 3-acre oasis on pond just outside amazing Sag Harbor
House
Sag Harbor, New York, USA

This 4-bedroom home in Sag Harbor is perfect for your escape to a serene and tranquil retreat in an unparalleled location. On a beautiful pond just outside Sag Harbor Village with a straight shot to the best ocean beaches, the home boasts a stunning 55-foot gunite pool with pool house for total relaxation between jaunts. The house adjoins the Long Pond Greenbelt and is a short walk to Mashashimuet Park with one of the East End's best playgrounds plus tennis and pickleball. With sleeping areas for up to ten, several outdoor seating areas, and a professional kitchen, this secluded property offers a peaceful getaway for guests.

Amenities:

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

Joels Lane by Rove | 5BR w/Heated Pool, Sauna, Gym
House
Sag Harbor, New York, USA

Summary:
Welcome to Joels Lane, a Rove Travel Home!

Rove offers beautifully designed residences with the quality and care of a 5-star hotel.

The Space:
Welcome to Joels Lane, a newly completed designer home just blocks from the heart of Sag Harbor Village. This five-bedroom, five-and-a-half-bathroom retreat spans over 3,700 square feet across three levels and was recently featured in Architectural Digest for its refined interiors and custom furnishings. At the center of the home is a light-filled great room with soaring ceilings, which flows into a cozy den, a formal living room with fireplace, and a chef’s kitchen with premium appliances and a spacious center island. The adjacent dining room features generous seating and a marble wet bar with sink, ideal for hosting.

The main-level primary suite includes a spa-style bathroom with soaking tub, double vanities, and a walk-in closet. Upstairs, there is one ensuite guest bedroom along with two additional guest rooms that share a full bathroom. The finished lower level offers a private movie theater, game room with a ping pong table, home gym, sauna, full bathroom, and a fifth bedroom. A lounge with sleeper sofa adds flexible space for guests or a home office setup.

Outdoors, enjoy the heated saltwater gunite pool with automatic cover, pool bath with kitchenette, and a spacious patio and lawn for lounging or dining under the sun. Located on a quiet street just a short stroll from Main Street Sag Harbor, the home is also close to a park, playground, and tennis courts. As part of your stay, a private 4-hour boat charter is included. Enjoy sunset cocktail cruises, fishing, waterfront dining, trips to secluded beaches, and excursions to Montauk, the North Fork, and Shelter Island.

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Room Configuration:
Primary Bedroom: 1 king bed
Second Bedroom: 1 full bed
Third Bedroom: 1 full bed
Fourth Bedroom: 1 full bed
Fifth Bedroom: 1 king bed

Amenities:
Work From Home: High-speed Wi-Fi, dedicated workspaces
Living: Fully equipped chef’s kitchen, luxury linens, and premium bath products
Support: 5-star service, housekeeping, maintenance, local recommendations
Laundry: In-unit washer/dryer available
Pet policy: Pets require an approval from the owner

Home Truths:
Our partner offers private boat charters for sunset cruises and weekend getaways for an additional fee. Costs will be paid directly to them.

Please note that our partner host requires all guests to sign a separate rental agreement after a booking is confirmed. This applies to all reservations at this home.

Please note that mid-stay cleans can be arranged upon request with our partner for an additional $320 fee. Cleaning costs will be paid to them directly.

The Neighborhood:
Sag Harbor is a charming and historic seaside village known for its rich maritime heritage, quaint streets lined with boutique shops, art galleries, and top-tier dining. With its picturesque harbor views and relaxed, sophisticated atmosphere, Sag Harbor offers a perfect blend of coastal elegance and small-town charm, making it an ideal retreat for those seeking a quintessential Hamptons experience.

Other Things to Note:
Pets are allowed with approval and a one time $150 charge. Rove requires a property rental agreement to be signed by the primary guest prior to arrival for all reservations at this home.

As a reminder, smoking is not allowed anywhere on the property, in the home or in the outside areas of the home. Smoking will result in a odor removal fee of no less than $500 and up to $1,000 as well as possible removal from the property.

Security Deposit Policy:
A refundable credit card hold of $1,000 is required as a security deposit for stays at this home to cover any property damage that may occur during your stay. A credit card is required for processing and the hold will be placed 48 hours prior to your arrival. The release of this hold will initiate 2 days after your departure following a departure inspection of the home by our local team.

Amenities:

Bedding/Linens • Balcony/Terrace • Tv • Laundry • Sports/Activities • Private Pool • Pool • Pet Friendly • Security/Safety • Fireplace/Heating • Kitchen • Wellness Facilities

Sag Harbor Vacation-Rentals on the Map

Compare the Best Vacation-Rentals in Sag Harbor – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
Baron's Cove 31 W. Water Street, Sag Harbor, NY, NY 11963 920 4.0 8.8 145 Click here
Faraway Sag Harbor 31 West Water Street, Sag Harbor, NY, 11963, USA 821 4.0 9.0 292 Click here
Villa Ebrar - Luxury with pool 16 Noyack Harbor Road, Sag Harbor, NY, NY 11963, USA 500 4.0 1 Click here
Sag Harbor Inn 45 West Water Street, Sag Harbor, NY, 11963, USA 238 3.0 9.4 569 Click here
Villa Zainip - Luxury with pool 77 Northside Drive, Sag Harbor, NY, NY 11963, USA 1178 4.0 1 Click here
Villa Keylime 3, Wilson Place, Sag Harbor, NY, 11963 1811 3.0 1 Click here
Villa KeyLime 3, Wilson Place, Sag Harbor, NY, 11963, USA 1241 4.0 1 Click here
Historic Sag Harbor Village Gem Sag Harbor, New York, USA 579 10.0 90 Click here
Dumar Villa by Rove - 6BR Family Home with Pool & Outdoor Spaces 22 Dumar Drive, Sag Harbor, NY, 11963, USA 1716 4.0 1 Click here
Whaling Captain Pierson's Cottage Sag Harbor, New York, USA 407 9.8 79 Click here
Entertainment Galore, Meadowood Manor by RoveTravel Millstone Road 1653, Sag Harbor, NY, 11963, USA 1778 4.0 1 Click here
Whaling Captain Pierson's Apartment Sag Harbor, New York, USA 351 10.0 70 Click here
Heated Pool, Grill, Breakwater by RoveTravel Franklin Avenue 71, Sag Harbor, NY, 11963 3014 4.0 1 Click here
Whaling Captain Pierson's Apartment TOO Sag Harbor, New York, USA 361 10.0 59 Click here
Coves Bay Beauty Sag Harbor, NY, USA 3853 4.0 1 Click here
Perfect Summer Retreat in Sag Harbor - Walk to Beach Sag Harbor, New York, USA 656 10.0 44 Click here
Villa Kimaal - Luxury with pool 33 Carroll Street, Sag Harbor, NY, NY 11963, USA 5693 4.0 1 Click here
COTTAGE IS AVAILABLE for FALL& WINTER STAYS sag harbor, New York, USA 576 9.8 40 Click here
Sag Harbor Inn 45 West Water Street, Sag Harbor, NY, NY 11963, USA 510 3.0 8.6 69 Click here
Sag Harbor Charmer - 2 Bedroom Cottage; Walk to Town Sag Harbor, New York, USA 623 9.6 34 Click here
The Cooper-Burke House Sag Harbor, New York, USA 430 10.0 28 Click here
Room 1 queen bed on waterfront + bikes and kayaks Sag Harbor, New York, USA 239 10.0 22 Click here
Bohemian chíc 2 bedroom home w/indoor pool & sauna in Sag Harbor. Sag Harbor, New York, USA 1051 9.8 14 Click here
Romantic Studio Cottage, Walk to Town Sag Harbor, New York, USA 457 10.0 12 Click here
Room3, best waterfront view +shared bath, bikes+kayaks Sag Harbor, New York, USA 214 10.0 10 Click here
Secluded Hamptons Cottage Sag Harbor, New York, USA 605 10.0 10 Click here
Sabbatical a Private guest cottage in Sag Harbor Sag Harbor, New York, USA 492 9.6 9 Click here
Island View Manor-Secluded, Pool Hot, Tub Sag Harbor, New York, USA 649 10.0 5 Click here
Charming Sag Harbor Cottage by the Beach! Sag Harbor, New York, USA 1085 10.0 5 Click here
Stay & Dine Sag Harbor, New York, USA 866 10.0 3 Click here
Sabbatical a Private guest cottage in Sag Harbor Sag Harbor, New York, USA 375 10.0 2 Click here
sunset bikes and kayaks in the village Sag Harbor, New York, USA 771 10.0 2 Click here
Authentic Sag harbor post and beam Sag Harbor, New York, USA 450 10.0 1 Click here
Tranquil getaway just steps from Long Pond Trails and Sag Harbor Village. Sag Harbor, New York, USA 599 10.0 1 Click here
Sag Harbor Enchanting Home near to Sandy Beach Sag Harbor, New York, USA 1093 10.0 1 Click here
Bayfront Sag Harbor ! Sunsets ! Dock and Mooring ! Avail for July 2024 ! n Sag Harbor, New York, USA 1315 10.0 1 Click here
Peaceful 3-acre oasis on pond just outside amazing Sag Harbor Sag Harbor, New York, USA 1656 1 Click here
Joels Lane by Rove | 5BR w/Heated Pool, Sauna, Gym Sag Harbor, New York, USA 5519 1 Click here

Note: The prices for each Vacation-Rentals in Sag Harbor do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Vacation rentals in Sag Harbor that include a pool include:

  • Baron's Cove.- Review Count: 145, Rating: 8.8
  • Faraway Sag Harbor.- Review Count: 292, Rating: 9.0
  • Villa Ebrar - Luxury with pool.- Review Count: 0, Rating: 0.0

Vacation rentals in Sag Harbor offering shuttle or transport options include:

  • Baron's Cove.- Review Count: 145, Rating: 8.8
  • Villa Ebrar - Luxury with pool.- Review Count: 0, Rating: 0.0
  • Villa Zainip - Luxury with pool.- Review Count: 0, Rating: 0.0

These vacation rentals in Sag Harbor provide spa or wellness access:

  • Baron's Cove.- Review Count: 145, Rating: 8.8
  • Faraway Sag Harbor.- Review Count: 292, Rating: 9.0

Family-friendly vacation rentals in Sag Harbor include:

  • Baron's Cove.- Review Count: 145, Rating: 8.8
  • Faraway Sag Harbor.- Review Count: 292, Rating: 9.0
  • Villa Ebrar - Luxury with pool.- Review Count: 0, Rating: 0.0

Pet-friendly vacation rentals in Sag Harbor include:

  • Baron's Cove.- Review Count: 145, Rating: 8.8
  • Dumar Villa by Rove - 6BR Family Home with Pool & Outdoor Spaces.- Review Count: 0, Rating: 0.0
  • Whaling Captain Pierson's Cottage.- Review Count: 79, Rating: 9.8

Vacation rentals in Sag Harbor that include breakfast options include:

  • Baron's Cove.- Review Count: 145, Rating: 8.8
  • Faraway Sag Harbor.- Review Count: 292, Rating: 9.0
  • Villa Ebrar - Luxury with pool.- Review Count: 0, Rating: 0.0

Vacation rentals in Sag Harbor with private or on-site parking include:

  • Baron's Cove.- Review Count: 145, Rating: 8.8
  • Faraway Sag Harbor.- Review Count: 292, Rating: 9.0
  • Villa Ebrar - Luxury with pool.- Review Count: 0, Rating: 0.0

Some of the best Vacation Rentals in Sag Harbor are:

  • Faraway Sag Harbor.- Review Count: 292, Rating: 9.0
  • Baron's Cove.- Review Count: 145, Rating: 8.8
  • Villa Ebrar - Luxury with pool.- Review Count: 0, Rating: 0.0

Some of the popular Vacation Rentals in Sag Harbor are:

  • Sag Harbor Inn.- Review Count: 569, Rating: 9.4
  • Faraway Sag Harbor.- Review Count: 292, Rating: 9.0
  • Baron's Cove.- Review Count: 145, Rating: 8.8