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

Holiday Homes in Wainscott

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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 !

!! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !
Wainscott
10.0 out of 10, Exceptional, (33 reviews)
"Thoroughly enjoyed our stay, property manager was incredibly helpful and responsive, highly recommend! "
United States
Leigh E.
The price is AU$3,268
includes taxes & fees
14 Oct - 15 Oct
!! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !
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, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
The price is AU$842
includes taxes & fees
4 Nov - 5 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A dining area with a round table, six chairs, and a chandelier.

3. Year round Jacuzzi - Blackberry Home

Year round Jacuzzi - Blackberry Home
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is AU$1,817
includes taxes & fees
5 Oct - 6 Oct
Year round Jacuzzi - Blackberry Home
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

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

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is AU$1,546
includes taxes & fees
5 Oct - 6 Oct
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

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

Spacious house in East Hampton with heated pool + WFH
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Great clean beautiful property."
United States
ANGELA S.
The price is AU$1,509
includes taxes & fees
22 Oct - 23 Oct
Spacious house in East Hampton with heated pool + WFH
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

6. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is AU$367
includes taxes & fees
2 Nov - 3 Nov
The SandPiper
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

7. Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (6 reviews)
"perfect for families"
United States
Okito H.
The price is AU$1,539
includes taxes & fees
5 Oct - 6 Oct
Minutes from the beach, brand new 4 bedroom
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

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

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is AU$840
includes taxes & fees
5 Oct - 6 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

9. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (48 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AU$454
includes taxes & fees
7 Oct - 8 Oct
Aqua Vista
An outdoor dining area with hanging lights, palm trees, and a bar.

10. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is AU$434
includes taxes & fees
5 Oct - 6 Oct
American Beech in Greenport - Petite King Room 7
A modern building with large windows overlooking a beach.

11. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (20 reviews)
"Views are incredible. Lucky enough to have had great weather before Memorial Day weekend! Our family loved it! Hot tub was wonderful."
United States
Donald J.
The price is AU$1,639
includes taxes & fees
5 Oct - 6 Oct
Beachfront Jacuzzi All Year - Black Swan Home
A wooden pathway leading to a beach with scattered rocks and greenery.

12. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is AU$640
includes taxes & fees
3 Nov - 4 Nov
Beach Block Hideaway
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

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (32 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AU$547
includes taxes & fees
1 Nov - 2 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

14. Amazing Southampton Home with Private Heated Pool

Amazing Southampton Home with Private Heated Pool
Southampton
9.0 out of 10, Wonderful, (2 reviews)
"Very cozy house in a great location!"
United States
Serina R.
The price is AU$2,311
includes taxes & fees
15 Oct - 16 Oct
Amazing Southampton Home with Private Heated Pool
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

15. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is AU$2,340
includes taxes & fees
5 Oct - 6 Oct
Jacuzzi year-round - Villa Luz Private Home
A coastal hotel with multiple buildings, a swimming pool, and a beach view.

16. Unit 1311: Cottage | Garden View | Deuce

Unit 1311: Cottage | Garden View | Deuce
Napeague
8.0 out of 10, Very good, (2 reviews)
"Great location a few steps always from the ocean and a few minutes away from town"
United States
Jessica S.
The price is AU$1,109
includes taxes & fees
5 Oct - 6 Oct
Unit 1311: Cottage | Garden View | Deuce
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a black table set for four.

17. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
The price is AU$3,138
includes taxes & fees
5 Oct - 6 Oct
Lovely & Spacious Sag Harbor escape with heated pool
A wooden house with a front porch, white railings, and a double door.

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

COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
Southampton
9.2 out of 10, Wonderful, (29 reviews)
"I loved the area and the home was beautiful and very spacious."
United States
Melissa
The price is AU$4,118
includes taxes & fees
5 Oct - 6 Oct
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
A wooden gate partially covered by lush green ivy.

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

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Southampton
10.0 out of 10, Exceptional, (16 reviews)
"We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!"
United States
Deborah V.
The price is AU$3,956
includes taxes & fees
1 Nov - 2 Nov
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

20. Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is AU$819
includes taxes & fees
8 Oct - 9 Oct
Immaculate Waterfront 2 bedroom!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wainscott Hotel Reviews

Montauk Blue Hotel

Montauk Blue Hotel

10/10 Excellent
"The staff was professional and very accommodating. Especialy Lauren at the front desk. The indoor pole was delightful."
Mary Ann 2-night trip
Posted 6 hours ago
Montauk Blue Hotel

Find out more about Wainscott

Wainscott Holiday Homes information

Number of reviews
257
Accommodation
1091 Holiday Homes
Lowest Price
AU$367
Highest Price
AU$4,118