A wooden church with a steeple, surrounded by trees and a clear blue sky.

Holiday Homes in Hamptons

  • 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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Hamptons 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, (2 reviews)
"The property was great for our Hamptons trip! Very clean and comfortable and communication was great"
United States
Katie B.
The price is AU$804
includes taxes & fees
8 Nov - 9 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

2. 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$851
includes taxes & fees
25 Oct - 26 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A dining area with a round table, six chairs, and a chandelier.

3. 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 AU$1,677
includes taxes & fees
22 Oct - 23 Oct
Year round Jacuzzi - Blackberry East Hampton Home
A covered outdoor area with a hot tub, wooden deck, and snow-covered trees.

4. 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$2,196
includes taxes & fees
28 Oct - 29 Oct
Jacuzzi year-round - Villa Luz Private Home
A modern living room with a sofa, armchairs, a coffee table, and a TV.

5. 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.
The price is AU$1,642
includes taxes & fees
3 Nov - 4 Nov
Minutes from the beach, brand new 3 bedroom
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

6. 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$795
includes taxes & fees
25 Oct - 26 Oct
Immaculate Waterfront 2 bedroom!
A modern building with large windows overlooking a beach.

7. 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 AU$1,674
includes taxes & fees
28 Oct - 29 Oct
Beachfront Jacuzzi All Year - Black Swan Home
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

8. 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$1,626
includes taxes & fees
22 Oct - 23 Oct
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

9. 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$1,518
includes taxes & fees
1 Nov - 2 Nov
Minutes from the beach, brand new 4 bedroom
A kitchen with a central island, white cabinetry, and a brick accent wall.

10. !! 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, (34 reviews)
"We loved this home and location! The home is so beautifully appointed and clean. It had everything you would ever need for a wonderful time with family and friends. The hosts were extremely responsive and easy to work with. We would go back in a heartbeat!"
United States
Suzanne B.
The price is AU$3,144
includes taxes & fees
19 Nov - 20 Nov
!! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !
A coastal hotel with multiple buildings, a swimming pool, and a beach view.

11. Unit 1311: Cottage | Garden View | Deuce

Unit 1311: Cottage | Garden View | Deuce
Napeague
8.8 out of 10, Excellent, (3 reviews)
"We only needed a one night stay but this place was clean and comfortable for what we needed! The beds are super comfortable."
United States
Sherry L.
The price is AU$850
includes taxes & fees
22 Oct - 23 Oct
Unit 1311: Cottage | Garden View | Deuce
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

12. 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$1,500
includes taxes & fees
22 Oct - 23 Oct
Spacious house in East Hampton with heated pool + WFH
A living room with a beige sofa, two woven ottomans, a framed car picture, and a door leading outside.

13. Prime location, walk to all, cozy cottage Westhampton Beach

Prime location, walk to all, cozy cottage Westhampton Beach
Westhampton Beach
10.0 out of 10, Exceptional, (4 reviews)
"Property was in easy walking distance from the village which made morning coffee runs a breeze. Very clean accommodations and large back yard."
United States
Matt S.
The price is AU$857
includes taxes & fees
26 Oct - 27 Oct
Prime location, walk to all, cozy cottage Westhampton Beach
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$1,689
includes taxes & fees
22 Oct - 23 Oct
Amazing Southampton Home with Private Heated Pool
A modern kitchen with grey cabinets, a stainless steel refrigerator, and a dining area with a black sofa and a small table.

15. Hamptons Retreat Enjoy the Fall Foilage and the Quiet Beaches

Hamptons Retreat Enjoy the Fall Foilage and the Quiet Beaches
east quogue
9.6 out of 10, Exceptional, (35 reviews)
"Great place, great host, easy process, definitely stay again."
United States
Andrew S.
The price is AU$961
includes taxes & fees
22 Oct - 23 Oct
Hamptons Retreat Enjoy the Fall Foilage and the Quiet Beaches
A wooden house with a front porch, white railings, and a double door.

16. 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$3,910
includes taxes & fees
22 Oct - 23 Oct
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

17. 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 AU$2,062
includes taxes & fees
22 Oct - 23 Oct
Newly Renovated Pristine Southampton Colonial
A dining area with a round table and chairs, surrounded by bookshelves filled with books and decorative items.

18. 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$3,930
includes taxes & fees
31 Oct - 1 Nov
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
A modern living room with a stone fireplace, two sofas, a coffee table, and a chandelier.

19. 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)
"The house was great. Pool was beautiful and everything was a 10 minute drive! Great place to relax"
United States
Judith M.
The price is AU$1,346
includes taxes & fees
26 Oct - 27 Oct
Elegant 5-Bedroom Hamptons Home with Private Pool
A modern kitchen with white cabinets, a dining area with a round table, and a living area with a sofa and decorative pillows.

20. Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (7 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is AU$2,098
includes taxes & fees
22 Oct - 23 Oct
Cozy Hamptons Escape 3BR Minutes From Beach!
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 Hamptons Hotel Reviews

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Gorgeous room! Felt like we were home"
Irene 4-night trip
Posted 20 hours ago
The Bentley Hotel Southampton

Find out more about Hamptons

Hamptons Holiday Homes information

Number of reviews
239
Accommodation
594 Holiday Homes
Lowest Price
AU$795
Highest Price
AU$3,930

Explore a world of travel with Expedia