Wainscott Vacation Home Rentals from CA $87: Search Top Private Vacation Homes for Rent

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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.

CA $2,899 total

includes taxes & fees

Nov 18 - Nov 19

A modern living room with a wooden accent wall, a flat-screen TV, a fireplace, and a dining area with a chair and table.

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

Bridgehampton

Katie B.

CA $797 total

includes taxes & fees

Nov 15 - Nov 16

A house with a sliding glass door, a white door, and a small porch with potted plants.

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

Sag Harbor

maria m.

CA $867 total

includes taxes & fees

Nov 14 - Nov 15

A modern living room with a flat-screen TV, a dining table with chairs, a sofa, a coffee table, and a chandelier.

4. Luxury Village Rental in the Heart of Sag Harbor

Sag Harbor

CA $1,327 total

includes taxes & fees

Nov 14 - Nov 15

A modern building with large windows overlooking a beach.

5. Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

John M.

CA $1,771 total

includes taxes & fees

Nov 15 - Nov 16

A modern wooden building with large windows, a balcony, and a view of autumn trees.

6. Serene Chic Hamptons oasis jus 1 block to waterfront + 8 minutes to Main Street

East Hampton

CA $1,673 total

includes taxes & fees

Nov 16 - Nov 17

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

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

East Hampton

ANGELA S.

CA $1,944 total

includes taxes & fees

Dec 1 - Dec 2

A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a black table set for four.

8. Lovely & Spacious Sag Harbor escape with heated pool

Sag Harbor

CA $3,014 total

includes taxes & fees

Nov 16 - Nov 17

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

9. The SandPiper

Pipes Cove

Manuela C.

CA $345 total

includes taxes & fees

Nov 30 - Dec 1

A residential property with a covered patio, outdoor seating, and a hot tub.

10. Jacuzzi year-round - Villa Luz Private Home

Hampon Bays

Annie B.

CA $1,615 total

includes taxes & fees

Nov 14 - Nov 15

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

11. Minutes from the beach, brand new 4 bedroom

Southampton

Okito H.

CA $1,490 total

includes taxes & fees

Nov 15 - Nov 16

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

12. Aqua Vista

Pipes Cove

Carey D.

CA $344 total

includes taxes & fees

Nov 18 - Nov 19

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

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

Pipes Cove

Callie E.

CA $496 total

includes taxes & fees

Nov 16 - Nov 17

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

14. Minutes from the beach, brand new 3 bedroom

Southampton

Kathy B.

CA $1,578 total

includes taxes & fees

Nov 16 - Nov 17

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

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

Southampton

Melissa

CA $4,183 total

includes taxes & fees

Nov 15 - Nov 16

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

16. Beach Block Hideaway

Pipes Cove

Teresa C.

CA $611 total

includes taxes & fees

Nov 16 - Nov 17

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

17. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

CA $414 total

includes taxes & fees

Nov 16 - Nov 17

A wooden gate partially covered by lush green ivy.

18. Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Southampton

Sarah

CA $4,129 total

includes taxes & fees

Nov 14 - Nov 15

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

19. Newly Renovated Pristine Southampton Colonial

Southampton

Brian M.

CA $2,084 total

includes taxes & fees

Nov 15 - Nov 16

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.

CA $778 total

includes taxes & fees

Nov 14 - Nov 15

View all properties

Learn more about Wainscott

Tucked between East Hampton and Bridgehampton, this Hamptons hamlet offers pristine beaches with gentle waves perfect for families. Rent bikes to explore Wainscott's farm stands selling local produce, then visit nearby Sag Harbour for boutique shopping and waterfront dining.

See all hotels in Wainscott

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

Top reviews in Wainscott

East Hampton House Resort

East Hampton North

10/10 Excellent

franca

An outdoor dining area with trees and tables under string lights.

The 1770 House Restaurant & Inn

East Hampton

10/10 Excellent

Anonymous traveller

A dining area with a fireplace, bookshelves, and a view of the bar area.

Bridgehampton Inn

Bridgehampton

10/10 Excellent

We had a wonderful stay at the Bridgehampton Inn from the moment we were welcomed at the entrance. Charming rooms, beautiful property and gardens, walkable to the shops and restaurants in town. Their store Loaves and Fishes is filled with great kitchen treasures. Breakfast which was included daily was amazing as was the dinner we enjoyed one evening. Great location to explore all of the Hamptons which we did! Can’t say enough about the staff. Every one of them went out of their way to...

Liliana