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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Wainscott holiday homes

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

1. 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 £429
includes taxes & fees
22 Sept - 23 Sept
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

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

East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
10.0 out of 10, Exceptional, (2 reviews)
"We have just returned from an amazing summer experience in East Hampton! From the minute I secured the booking to checkout, everything was perfectly smooth! The house was so wonderful, every design detail and amenity…. It was truly like the best of all possible creature comforts…. Fully stocked kitchen, incredible fire pit for late evening s’mores, extraordinary huge pool, patio with outdoor speakers, and enough indoor space meticulously designed and decorated that proved our dream vacation...
United States
GINA W.
The price is £944
includes taxes & fees
13 Sept - 14 Sept
East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

3. 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 £825
includes taxes & fees
8 Sept - 9 Sept
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A dining area with a round table, six chairs, and a chandelier.

4. BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
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 £1,267
includes taxes & fees
8 Sept - 9 Sept
BlackBerry Private home with jacuzzi yearlong
A wooden pathway leading to a beach with scattered rocks and greenery.

5. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is £303
includes taxes & fees
7 Sept - 8 Sept
Beach Block Hideaway
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

Spacious house in East Hampton with heated pool + WFH
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Great clean beautiful property."
United States
ANGELA S.
The price is £843
includes taxes & fees
4 Oct - 5 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.

7. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (51 reviews)
"access"
United States
Timothy
The price is £264
includes taxes & fees
10 Sept - 11 Sept
The SandPiper
A beach with people relaxing, a pier extending into the water, and a clear sky.

8. 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, (30 reviews)
"We had a great stay!! "
United States
Callie E.
The price is £308
includes taxes & fees
8 Sept - 9 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A modern kitchen with a black and white color scheme, a central island, and built-in appliances.

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

Spacious & Modern 5-bedroom in Sag Harbor, walk to bay
Sag Harbor
The price is £1,402
includes taxes & fees
18 Sept - 19 Sept
Spacious & Modern 5-bedroom in Sag Harbor, walk to bay
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

10. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (45 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is £282
includes taxes & fees
8 Sept - 9 Sept
Aqua Vista
A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

11. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (57 reviews)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is £990
includes taxes & fees
15 Sept - 16 Sept
Work and Play Special! Extended Stay Discount
A coastal hotel with multiple buildings, a swimming pool, and a beach view.

12. 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 £555
includes taxes & fees
8 Sept - 9 Sept
Unit 1311: Cottage | Garden View | Deuce
An outdoor dining area with hanging lights, palm trees, and a bar.

13. 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 £259
includes taxes & fees
16 Sept - 17 Sept
American Beech in Greenport - Petite King Room 7
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

14. 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 £973
includes taxes & fees
7 Sept - 8 Sept
Minutes from the beach, brand new 4 bedroom
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

15. 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 £867
includes taxes & fees
5 Oct - 6 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A modern living room with a sofa, armchairs, a coffee table, and a TV.

16. Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
10.0 out of 10, Exceptional, (4 reviews)
"Great location. Loved the yard but for small pets the fence has some areas they could get under but overall it worked out. Just kept an eye on them.House very clean, comfortable. Host communication was excellent and would highly recommend for a visit to Southampton. Easy walk into town."
United States
Kathy B.
The price is £1,045
includes taxes & fees
8 Sept - 9 Sept
Minutes from the beach, brand new 3 bedroom
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

17. Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, Exceptional, (43 reviews)
"My family and I really enjoyed this home. Everything you can think of is provided for you. We would definitely stay here again!"
United States
Sarah A.
The price is £715
includes taxes & fees
15 Sept - 16 Sept
Elegant 5-Bedroom Hamptons Home with Private Pool
A modern building with large windows overlooking a beach.

18. Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.4 out of 10, Exceptional, (19 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 £1,166
includes taxes & fees
9 Sept - 10 Sept
Black Swan Beachfront Home with Jacuzzi year round
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 £1,260
includes taxes & fees
1 Oct - 2 Oct
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

20. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (14 reviews)
"We had a wonderful girls weekend in Greenport. The house was perfect for the three of us. Loved the location. We didn’t get to use the back area due to the weather, but it looked so inviting. Next time!"
United States
Melissa A.
The price is £523
includes taxes & fees
17 Sept - 18 Sept
Renovated Townhouse walk to all
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.
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Top Wainscott Hotel Reviews

The Hampton Maid

The Hampton Maid

10/10 Excellent
"Restaurant was exceptional"
Ruby 2-night trip
Posted 7 hours ago
The Hampton Maid

Find out more about Wainscott

Wainscott Holiday Homes information

Number of reviews
324
Accommodation
1139 Holiday Homes
Lowest Price
£259
Highest Price
£1,267