Wainscott, NY Vacation Homes from ￥39,933

A coastal landscape with a beach, ocean waves, and a sunset sky.

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Our top choices for Wainscott vacation homes

A kitchen with a central island, white cabinetry, and a brick accent wall.

1. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

Wainscott

Suzanne B.

￥363,322 total

includes taxes & fees

Nov 19 - Nov 20

A driveway with a parked car, surrounded by trees and illuminated pathway lights.

2. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton

Katie B.

￥92,040 total

includes taxes & fees

Nov 8 - Nov 9

A dining area with a round table, six chairs, and a chandelier.

3. Year round Jacuzzi - Blackberry East Hampton Home

East Hampton

Suzanne R.

￥198,138 total

includes taxes & fees

Oct 25 - Oct 26

A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

4. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Southampton

Justin

￥93,651 total

includes taxes & fees

Oct 25 - Oct 26

A backyard with a swimming pool, wicker lounge chairs, and potted plants.

5. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Sag Harbor

maria m.

￥181,870 total

includes taxes & fees

Oct 24 - Oct 25

A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

6. Spacious house in East Hampton with heated pool + WFH

East Hampton

ANGELA S.

￥167,786 total

includes taxes & fees

Oct 25 - Oct 26

A covered patio with outdoor furniture, a door, and a view of a residential area.

7. The SandPiper

Pipes Cove

Manuela C.

￥40,300 total

includes taxes & fees

Nov 10 - Nov 11

A metal compass sign with the words "AQUA VISTA GREENPORT" on a building's exterior wall.

8. Aqua Vista

Pipes Cove

Kerri L.

￥39,933 total

includes taxes & fees

Nov 9 - Nov 10

A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

9. Minutes from the beach, brand new 4 bedroom

Southampton

Okito H.

￥173,872 total

includes taxes & fees

Oct 25 - Oct 26

A modern building with large windows overlooking a beach.

10. Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

Donald J.

￥183,796 total

includes taxes & fees

Oct 28 - Oct 29

A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

11. Amazing Southampton Home with Private Heated Pool

Southampton

Serina R.

￥194,026 total

includes taxes & fees

Oct 25 - Oct 26

A modern living room with a sofa, armchairs, a coffee table, and a TV.

12. Minutes from the beach, brand new 3 bedroom

Southampton

Kathy B.

￥184,079 total

includes taxes & fees

Nov 10 - Nov 11

A small, single-story house with a gabled roof, a front door, and a number "401" on the door.

13. Beach Block Hideaway

Pipes Cove

Teresa C.

￥70,550 total

includes taxes & fees

Nov 3 - Nov 4

A porch with a white railing, a small blue house decoration, and a 'Gone' sign.

14. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Pipes Cove

"We had a wonderful stay in Greenport! The location was absolutely perfect, and one of the things we loved most was being able to walk to town and the beautiful harbor. Everything was so conveniently located, from the charming shops and wonderful restaurants to the lovely waterfront, making it easy to enjoy everything Greenport has to offer without needing to drive. We would happily stay here again and highly recommend this place to anyone looking for a wonderful Greenport getaway!"

Nino

￥55,598 total

includes taxes & fees

Nov 3 - Nov 4

A coastal hotel with multiple buildings, a swimming pool, and a beach view.

15. Unit 1311: Cottage | Garden View | Deuce

Napeague

Sherry L.

￥96,431 total

includes taxes & fees

Oct 25 - Oct 26

A patio area with wicker chairs and a table, surrounded by gravel and plants.

16. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

￥47,990 total

includes taxes & fees

Oct 25 - Oct 26

A wooden house with a front porch, white railings, and a double door.

17. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

Southampton

Melissa

￥452,901 total

includes taxes & fees

Oct 25 - Oct 26

A covered outdoor area with a hot tub, wooden deck, and snow-covered trees.

18. Jacuzzi year-round - Villa Luz Private Home

Hampon Bays

Annie B.

￥243,128 total

includes taxes & fees

Oct 28 - Oct 29

A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

19. Newly Renovated Pristine Southampton Colonial

Southampton

Brian M.

￥240,502 total

includes taxes & fees

Oct 25 - Oct 26

A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

20. Immaculate Waterfront 2 bedroom!

Hampton Bays

Michael L.

￥90,071 total

includes taxes & fees

Oct 25 - Oct 26

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Top Wainscott Hotel Reviews

Montauk Yacht Club

10/10 Excellent

"Excellent hotel, clean and spacious rooms, friendly and attentive staff."

Faraway Sag Harbor

8/10 Good

"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."

Zey Hotel

10/10 Excellent

"The hotel had a good vibe and energy! Lots of artwork and was very charming. It has a bed and breakfast feel to it. The parking is behind the hotel and free and convenient. It’s right on Main Street and walking distance to all restaurants and bars. The staff especially James was warm and friendly and accommodating. We had a great time checking out all the cool lounge areas in the hotel. The room was clean and charming as well. Would definitely stay here again the next time we visit Greenport"

Find out more about Wainscott

Wainscott Vacation Homes information

Number of reviews	259
Accommodation	1132 Vacation Homes
Lowest Price	￥39,933
Highest Price	￥452,901

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Wainscott vacation homes

1. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

2. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

3. Year round Jacuzzi - Blackberry East Hampton Home

4. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

5. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard