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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Wainscott vacation 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 AED 1,047
AED 2,157 total
includes taxes & fees
1 Nov - 2 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A dining area with a round table, six chairs, and a chandelier.

2. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton 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 AED 323
AED 4,741 total
includes taxes & fees
8 Oct - 9 Oct
Year round Jacuzzi - Blackberry East Hampton Home
A rectangular swimming pool with a pebble border and a fire feature in the center.

3. Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids

Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
East Hampton North
10.0 out of 10, Exceptional, (1 review)
The price is AED 881
AED 3,511 total
includes taxes & fees
8 Oct - 9 Oct
Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
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!

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 AED 628
AED 2,195 total
includes taxes & fees
11 Oct - 12 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

5. 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 AED 2,083
AED 4,092 total
includes taxes & fees
8 Oct - 9 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.

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, (2 reviews)
"Great clean beautiful property."
United States
ANGELA S.
The price is AED 1,653
AED 3,907 total
includes taxes & fees
19 Oct - 20 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, (54 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is AED 349
AED 906 total
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.

8. 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 AED 1,653
AED 4,075 total
includes taxes & fees
8 Oct - 9 Oct
Minutes from the beach, brand new 4 bedroom
A modern building with large windows overlooking a beach.

9. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (21 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 AED 518
AED 4,530 total
includes taxes & fees
12 Oct - 13 Oct
Beachfront Jacuzzi All Year - Black Swan Home
A bathroom with a white sink, vanity, and toilet.

10. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
The price is AED 5,620
AED 8,175 total
includes taxes & fees
8 Oct - 9 Oct
Lovely & Spacious Sag Harbor escape with heated pool
A wooden pathway leading to a beach with scattered rocks and greenery.

11. 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 AED 716
AED 1,653 total
includes taxes & fees
3 Nov - 4 Nov
Beach Block Hideaway
A wooden house with a front porch, white railings, and a double door.

12. 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 AED 7,852
AED 10,614 total
includes taxes & fees
11 Oct - 12 Oct
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

13. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AED 533
AED 1,175 total
includes taxes & fees
29 Oct - 30 Oct
Aqua Vista
A beach with people relaxing, a pier extending into the water, and a clear sky.

14. 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, (33 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AED 533
AED 1,414 total
includes taxes & fees
1 Nov - 2 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
An outdoor dining area with hanging lights, palm trees, and a bar.

15. 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 AED 731
AED 1,125 total
includes taxes & fees
8 Oct - 9 Oct
American Beech in Greenport - Petite King Room 7
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

16. 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 AED 2,527
AED 5,146 total
includes taxes & fees
28 Oct - 29 Oct
Amazing Southampton Home with Private Heated Pool
A coastal hotel with multiple buildings, a swimming pool, and a beach view.

17. 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 AED 1,109
AED 2,260 total
includes taxes & fees
12 Oct - 13 Oct
Unit 1311: Cottage | Garden View | Deuce
A modern living room with a sofa, armchairs, a coffee table, and a TV.

18. Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
10.0 out of 10, Exceptional, (5 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.
Minutes from the beach, brand new 3 bedroom
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

19. 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 AED 411
AED 6,119 total
includes taxes & fees
12 Oct - 13 Oct
Jacuzzi year-round - Villa Luz Private Home
A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

20. Newly Renovated Pristine Southampton Colonial

Newly Renovated Pristine Southampton Colonial
Southampton
9.8 out of 10, Exceptional, (12 reviews)
"Great property, worked perfectly for my crew that was in town for an event. Great communication with Brian the owner and very easy stay. Would stay again!"
United States
Brian M.
The price is AED 6,608
AED 9,967 total
includes taxes & fees
8 Oct - 9 Oct
Newly Renovated Pristine Southampton Colonial
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

Offshore Montauk

Offshore Montauk

10/10 Excellent
"Great"
Dillon 1-night trip
Posted 22 hours ago
Offshore Montauk