A man carrying a woman in front of a pool with two American flags, surrounded by greenery and a monument.

Holiday Homes in Town of Southampton

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Top Cities in Town of Southampton

A coastal landscape with a sandy beach, a forested area, and a golf course.
Holiday HomesHoliday Homes

Riverhead

Riverhead
A sandy beach path with wooden fences on either side leading to the ocean.
Holiday HomesHoliday Homes

Hampton Bays

Hampton Bays

Our top choices for Town of Southampton holiday homes

A terrace with stone flooring, wooden chairs, and tables overlooking a vineyard.

1. WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly
Westhampton Beach
10.0 out of 10, Exceptional, (220 reviews)
"Mark was a great Host. Very easy to communicate with and house was as advertised. We had a great stay with our family of 6."
United States
Sarah A.
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly
A large, two-story house with a wrap-around porch and a steeply pitched roof.

2. 11-Bedroom Mansion with a Seasonal Outdoor Pool open now plus 10.5 bathrooms

11-Bedroom Mansion with a Seasonal Outdoor Pool open now plus 10.5 bathrooms
Eastport
9.4 out of 10, Exceptional, (40 reviews)
"What a perfect venue to celebrate a special occasion! We chose this house for my husband’s birthday and it exceeded our expectations. The rooms are generously sized with bathrooms in nearly every room, a huge plus for a large group. Jhoanna was fantastic, always quick to respond and so accommodating. We would absolutely come back and highly recommend this stay!"
United States
Stacey S.
11-Bedroom Mansion with a Seasonal Outdoor Pool open now plus 10.5 bathrooms
A wooden boardwalk leading to a beach with dunes and a clear sky.

3. Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.

Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
Westhampton Beach
9.8 out of 10, Exceptional, (81 reviews)
"The view is spectacular and would love to go back and visit again."
United States
Al C.
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.

4. Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms

Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
Sagaponack
10.0 out of 10, Exceptional, (30 reviews)
"This outstanding property provided the perfect balance of space for family fun and quiet retreats for personal time. I highly recommend it for anyone looking to plan an extended family getaway!"
United States
Anne Marie
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
A modern kitchen with white cabinetry, a wooden island, and a dining area with a bench and chairs.

5. Completely Renovated Modern Hampton Bays Retreat with Brand New Pool,...

Completely Renovated Modern Hampton Bays Retreat with Brand New Pool,...
Hampton Bays
10.0 out of 10, Exceptional, (4 reviews)
"Great property in a great spot. Lots room for extended family."
United States
Kimberly W.
Completely Renovated Modern Hampton Bays Retreat with Brand New Pool,...

6. Spacious Southampton Home in Shinnecock Hills, Central Between Southampton,...

Spacious Southampton Home in Shinnecock Hills, Central Between Southampton,...
Southampton
9.8 out of 10, Exceptional, (8 reviews)
"We had a wonderful weekend here. The house was beautiful and spacious and great for a group of friends. The deck and pool area were also amazing. Owner was responsive and easily reachable if needed. We really enjoyed ourselves and would totally recommend!"
United States
Ally G.
Spacious Southampton Home in Shinnecock Hills, Central Between Southampton,...
A wooden deck with outdoor furniture, a pool, and a view of the sea.

7. Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms
Hampton Bays
10.0 out of 10, Exceptional, (47 reviews)
"Beautiful house with great views and great host. "
United States
Anonymous traveller
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms
A deck with a table and chairs, a picnic table, and a covered area with an umbrella.

8. 10 Bedroom Hampton House with a regulation size Pickleball court

10 Bedroom Hampton House with a regulation size Pickleball court
Hampton Bays
10.0 out of 10, Exceptional, (35 reviews)
"Location of this property is impeccable."
United States
Stephen M.
10 Bedroom Hampton House with a regulation size Pickleball court
A spacious dining area with a large table, white chairs, and a chandelier.

9. Private Bayfront Living, Water Views

Private Bayfront Living, Water Views
Southampton
9.4 out of 10, Exceptional, (8 reviews)
"Perfect stay, thank you."
United States
Robert H.
Private Bayfront Living, Water Views
A sandy beach path leading to a body of water, surrounded by dense green foliage and a clear sky.

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

Hamptons Retreat Enjoy the Fall Foilage and the Quiet Beaches
east quogue
9.8 out of 10, Exceptional, (34 reviews)
"Great place, great host, easy process, definitely stay again."
United States
Andrew S.
Hamptons Retreat Enjoy the Fall Foilage and the Quiet Beaches
A two-story house with a swimming pool, outdoor furniture, and a covered patio area.

11. Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Hampton Bays
9.6 out of 10, Exceptional, (82 reviews)
"The house was perfect for our large family from Mississippi and Tennessee to use while attending a wedding in the area. Lots of bedrooms and bathroom to accommodate everyone. The location was near all the places we needed to be. Megan communicated frequently with me about any and all questions and inquiries I had."
United States
Angela W.
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
A curved swimming pool with a stone deck, surrounded by a brick wall and a white railing.

12. Beautiful Hamptons home close to beaches, shopping, & restaurants!

Beautiful Hamptons home close to beaches, shopping, & restaurants!
Hampton Bays
10.0 out of 10, Exceptional, (25 reviews)
"Great neighborhood, lots of open space, pool was very clean, amenities were pristine. I would definitely go back and highly recommend to others. "
United States
Christine P.
Beautiful Hamptons home close to beaches, shopping, & restaurants!
A house with grey siding, white trim, and a stone patio.

13. Cozy Cottage by Shinnecock Canal and by Meschutt Beach! 🏖️

Cozy Cottage by Shinnecock Canal and by Meschutt Beach! 🏖️
Hampton Bays
9.4 out of 10, Exceptional, (30 reviews)
"We were up from Maryland for a wedding. Since it was just three of us, the size was just right. Anymore people I think it would have been hard with just one shower. The location was FABULOUS for the various venues for the wedding events. We were close to everything! Although a small cottage, it was nicely done with everything you'd need. Even though we did not have to cook all weekend the kitchen was well supplied with what you would need. I loved the lovely patio and outdoor living space (my...
United States
Thea
Cozy Cottage by Shinnecock Canal and by Meschutt Beach! 🏖️
A modern kitchen with a dining area, large sliding glass doors to a deck, and a chandelier.

14. Timeless Shingled Hampton Bays Retreat with Private Heated Pool, An...

Timeless Shingled Hampton Bays Retreat with Private Heated Pool, An...
Hampton Bays
10.0 out of 10, Exceptional, (2 reviews)
"Great relaxing place for our family with adultish kids and friends. "
United States
Gaby S.
Timeless Shingled Hampton Bays Retreat with Private Heated Pool, An...
A swimming pool with lounge chairs, a house with a porch, and a white picket fence.

15. Tranquil Remsenburg Home, Private Heated Pool, An Inviting Escape for...

Tranquil Remsenburg Home, Private Heated Pool, An Inviting Escape for...
Remsenburg
9.0 out of 10, Wonderful, (2 reviews)
"Comfortable clean house."
United States
Meg T.
Tranquil Remsenburg Home, Private Heated Pool, An Inviting Escape for...
A two-story house with a swimming pool, patio furniture, and a well-maintained lawn.

16. Cove View Manor of Sag Harbor

Cove View Manor of Sag Harbor
Sag Harbor
10.0 out of 10, Exceptional, (78 reviews)
"Both the property and the host Michael are exceptional! I'm a repeat guest and look forward to staying here every year. It's meticulously clean and has everything you could need!"
United States
Christine F.
Cove View Manor of Sag Harbor
A narrow staircase with wooden walls and a small window at the top.

17. Exclusive Bayfront Oasis Awaits You In East Quogue

Exclusive Bayfront Oasis Awaits You In East Quogue
East Quogue
10.0 out of 10, Exceptional, (13 reviews)
"Great views, clean home, communicative host."
United States
Ellen L.
Exclusive Bayfront Oasis Awaits You In East Quogue
A room with a large bay window overlooking a beach, a ceiling fan, and a view of outdoor furniture.

18. Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets

Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets
west hampton beach
10.0 out of 10, Exceptional, (86 reviews)
"Beautiful ocean front location right on the beach. So relaxing. "
United States
James M.
Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

19. 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$1,982
includes taxes & fees
7 Oct - 8 Oct
Minutes from the beach, brand new 4 bedroom
A large house with a swimming pool, deck chairs, and string lights.

20. Fun for All Ages! In the Heart of the Hamptons!

Fun for All Ages! In the Heart of the Hamptons!
Sag Harbor
10.0 out of 10, Exceptional, (99 reviews)
"Awesome property for a big family/friends getaway! 5min ride right into sag harbor! Our host, Jay, was great! Communication was clear and prompt. Highly recommend!"
United States
Brice D.
Fun for All Ages! In the Heart of the Hamptons!
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 Town of Southampton Hotel Reviews

Sag Harbor Inn

Sag Harbor Inn

10/10 Excellent
"Great place to stay in Sag Harbor. Walking distance to everything and also quiet and peaceful. Helpful staff and nice that there was 24/7 coffee and tea in lobby."
Stephen 2-night trip
Posted 1 day ago
Sag Harbor Inn

Find out more about Town of Southampton

Town of Southampton Holiday Homes information

Number of reviews
812
Accommodation
589 Holiday Homes
Lowest Price
AU$1,982
Highest Price
AU$1,982

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