Wainscott Vacation Homes

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

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Our top choices for Wainscott holiday homes

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

1. !! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !

Wainscott

Leigh E.

HK$19,021 total

includes taxes & fees

5 Oct - 6 Oct

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

Robert R.

HK$4,605 total

includes taxes & fees

22 Sept - 23 Sept

A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

3. East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton North

Carolyn C.

HK$10,365 total

includes taxes & fees

16 Sept - 17 Sept

A spacious room with a wooden dining table, white chairs, and a large window providing a view of the outdoors.

4. Designer East Hampton Farmhouse - Bike to Amagansett, EH & Ocean Beaches, Pool

East Hampton North

HK$9,077 total

includes taxes & fees

28 Sept - 29 Sept

A spacious living room with a stone fireplace, wooden beams, a white sofa, and a cowhide rug.

5. Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

Sag Harbor

Nadja B.

HK$11,262 total

includes taxes & fees

16 Sept - 17 Sept

A wooden pathway leading to a beach with scattered rocks and greenery.

6. Beach Block Hideaway

Pipes Cove

Teresa C.

HK$3,136 total

includes taxes & fees

15 Sept - 16 Sept

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

7. Unit 1311: Cottage | Garden View | Deuce

Napeague

Jessica S.

HK$5,995 total

includes taxes & fees

13 Sept - 14 Sept

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

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

East Hampton

ANGELA S.

HK$8,852 total

includes taxes & fees

4 Oct - 5 Oct

A beach with people relaxing, a pier extending into the water, and a clear sky.

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

Pipes Cove

Callie E.

HK$3,337 total

includes taxes & fees

16 Sept - 17 Sept

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

10. Aqua Vista

Pipes Cove

Kerri L.

HK$2,509 total

includes taxes & fees

7 Oct - 8 Oct

A modern building with large windows overlooking a beach.

11. Black Swan Beachfront Home with Jacuzzi year round

Hampton Bays

Donald J.

HK$9,493 total

includes taxes & fees

16 Sept - 17 Sept

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

12. The SandPiper

Pipes Cove

Timothy

HK$2,948 total

includes taxes & fees

28 Sept - 29 Sept

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

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

Southampton

Justin

HK$8,086 total

includes taxes & fees

13 Sept - 14 Sept

A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

14. Work and Play Special! Extended Stay Discount

Shelter Island

Kathleen Andrews K.

HK$10,438 total

includes taxes & fees

16 Sept - 17 Sept

A modern kitchen with a black and white color scheme, a central island, and built-in appliances.

15. Spacious & Modern 5-bedroom in Sag Harbor, walk to bay

Sag Harbor

HK$15,150 total

includes taxes & fees

16 Sept - 17 Sept

An outdoor dining area with hanging lights, palm trees, and a bar.

16. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

HK$2,804 total

includes taxes & fees

16 Sept - 17 Sept

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

17. Minutes from the beach, brand new 3 bedroom

Southampton

Kathy B.

HK$11,262 total

includes taxes & fees

15 Sept - 16 Sept

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

18. Minutes from the beach, brand new 4 bedroom

Southampton

Okito H.

HK$11,925 total

includes taxes & fees

15 Sept - 16 Sept

A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

19. Villa Luz Family Home w/ heated pool & jacuzzi

Hampon Bays

Carola C.

HK$12,795 total

includes taxes & fees

12 Sept - 13 Sept

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Top Wainscott Hotel Reviews

Montauk Blue Hotel

8/10 Good

"chairs forvthe beach"

Faraway Sag Harbor

8/10 Good

"Faraway has been renovated Beautifully. The food has improved since Baron's Cove. The pool would benefit improving service and perhaps combining the food / drinks servers and pool attendants. In addition since we have been guests of the older Hotel, Baron's Cove for 16 years it would have been meaningful to have the new staff welcome guests and perhaps give a priority rate or welcome massage etc."

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