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

Holiday Homes in Hamptons

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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 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, (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 €521
includes taxes & fees
2 Nov - 3 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 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 €1,167
includes taxes & fees
4 Oct - 5 Oct
Year round Jacuzzi - Blackberry Home
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

3. 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 €1,496
includes taxes & fees
2 Nov - 3 Nov
Jacuzzi year-round - Villa Luz Private Home
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

4. 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 €506
includes taxes & fees
8 Oct - 9 Oct
Immaculate Waterfront 2 bedroom!
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

5. 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 €982
includes taxes & fees
4 Oct - 5 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.

6. 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 €845
includes taxes & fees
28 Oct - 29 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
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, (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 €1,089
includes taxes & fees
4 Oct - 5 Oct
Beachfront Jacuzzi All Year - Black Swan Home
A kitchen with a central island, white cabinetry, and a brick accent wall.

8. !! 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 €2,023
includes taxes & fees
14 Oct - 15 Oct
!! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

9. 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 €964
includes taxes & fees
1 Nov - 2 Nov
Spacious house in East Hampton with heated pool + WFH
Roger’s Beach

10. 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, (3 reviews)
"Erica was very communicative and helpful. Very cozy with a great location."
United States
Chris J.
The price is €652
includes taxes & fees
19 Oct - 20 Oct
Prime location, walk to all, cozy cottage Westhampton Beach
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

11. 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 €995
includes taxes & fees
4 Oct - 5 Oct
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
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 €678
includes taxes & fees
5 Oct - 6 Oct
Unit 1311: Cottage | Garden View | Deuce
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

13. 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 €865
includes taxes & fees
4 Oct - 5 Oct
Elegant 5-Bedroom Hamptons Home with Private Pool
A wooden house with a front porch, white railings, and a double door.

14. 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 €2,568
includes taxes & fees
3 Nov - 4 Nov
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

15. 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 €1,242
includes taxes & fees
20 Oct - 21 Oct
Amazing Southampton Home with Private Heated Pool
A wooden gate partially covered by lush green ivy.

16. 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 €2,517
includes taxes & fees
1 Nov - 2 Nov
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
A modern living room with a grey sofa, round coffee table, and a white fireplace.

17. 5 Bedrooms! 4 Min to the Beach! HEATED POOL!

5 Bedrooms! 4 Min to the Beach! HEATED POOL!
Westhampton Beach
10.0 out of 10, Exceptional, (6 reviews)
"awesome house and awesome host"
United States
Matthew M.
The price is €2,404
includes taxes & fees
4 Oct - 5 Oct
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
A sandy beach path with wooden fencing leading to the ocean.

18. Montauk Beach Retreat — 3BR, Steps to Beach, BBQ, Patio & Outdoor Shower

Montauk Beach Retreat — 3BR, Steps to Beach, BBQ, Patio & Outdoor Shower
Culloden Shores
8.6 out of 10, Excellent, (4 reviews)
"Definitely more space than expected, and super close to everything in Montauk. Planning on coming back next year!"
United States
Nick M.
The price is €1,035
includes taxes & fees
16 Oct - 17 Oct
Montauk Beach Retreat — 3BR, Steps to Beach, BBQ, Patio & Outdoor Shower
A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

19. 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 €2,632
includes taxes & fees
16 Oct - 17 Oct
Newly Renovated Pristine Southampton Colonial
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 €1,393
includes taxes & fees
4 Oct - 5 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.
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Top Hamptons Hotel Reviews

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Kind of expected to be disappointed. However, really delighted. Room was lovely, clean and thoughtful appointments. Location was OK, but doable."
Randi 2-night trip
Posted 16 hours ago
The Bentley Hotel Southampton

Find out more about Hamptons

Hamptons Holiday Homes information

Number of reviews
230
Accommodation
594 Holiday Homes
Lowest Price
€506
Highest Price
€2,632

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