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

Compare and save

  • 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
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

Our top choices for Town of Southampton holiday homes

A large house with a swimming pool, hot tub, and outdoor seating area surrounded by trees.

1. Casa Newmark Holiday home 7 BestStayz.1

Casa Newmark Holiday home 7 BestStayz.1
5.0 star property
Sagaponack
Casa Newmark Holiday home 7 BestStayz.1
Two wooden Adirondack chairs facing a calm body of water with a dock and buildings in the background.

2. Bungalow 8 - 1br, Waterfront

Bungalow 8 - 1br, Waterfront
3.0 star property
Westhampton Beach
Bungalow 8 - 1br, Waterfront
A modern kitchen with a central island, bar stools, stainless steel appliances, and wooden flooring.

3. The Mainstay - Entire Bed & Breakfast

The Mainstay - Entire Bed & Breakfast
2.0 star property
Southampton
The Mainstay - Entire Bed & Breakfast

4. Sage and Madison House - Hatfield Suite - 3rd Floor

Sage and Madison House - Hatfield Suite - 3rd Floor
3.5 star property
Sag Harbor
Sage and Madison House - Hatfield Suite - 3rd Floor
Two wooden Adirondack chairs facing a sunset over a body of water, with a wooden deck and a building in the background.

5. Bungalow 3 - 1br, Waterfront

Bungalow 3 - 1br, Waterfront
3.0 star property
Westhampton Beach
Bungalow 3 - 1br, Waterfront

6. Sweet Retreat Luxury Southampton 4BR Pool & Jacuzzi

Sweet Retreat Luxury Southampton 4BR Pool & Jacuzzi
4.0 star property
Southampton
Sweet Retreat Luxury Southampton 4BR Pool & Jacuzzi
A modern living room with a sofa, a coffee table, and a dining area with chairs. There is a kitchen visible in the background.

7. SH001 5 Bedroom Holiday home By Senstay

SH001 5 Bedroom Holiday home By Senstay
3.5 star property
Sagaponack
SH001 5 Bedroom Holiday home By Senstay

8. Classic 6BR Amazing Luxury Southampton Home-6br Pool Jacuzzi

Classic 6BR Amazing Luxury Southampton Home-6br Pool Jacuzzi
3.5 star property
Southampton
Classic 6BR Amazing Luxury Southampton Home-6br Pool Jacuzzi
Two wooden Adirondack chairs facing a calm body of water with a dock and buildings in the background.

9. Bungalow 4 - 1br, Waterfront

Bungalow 4 - 1br, Waterfront
3.0 star property
Westhampton Beach
Bungalow 4 - 1br, Waterfront
A modern kitchen with a central island, stainless steel appliances, and ample natural light from large windows.

10. Shinnecock Sanctuary

Shinnecock Sanctuary
4.0 star property
Southampton
Shinnecock Sanctuary
A wooden pathway flanked by stone walls and dense greenery, leading towards a building with a visible window.

11. Bungalow 1 - 1br, Water View

Bungalow 1 - 1br, Water View
3.0 star property
Westhampton Beach
Bungalow 1 - 1br, Water View
A wooden pathway flanked by stone walls and dense greenery, leading towards a building with a visible window.

12. Bungalow 2 - 1br, Water View

Bungalow 2 - 1br, Water View
3.0 star property
Westhampton Beach
Bungalow 2 - 1br, Water View
Two wooden Adirondack chairs facing a sunset over a body of water, with a wooden deck and a building in the background.

13. Bungalow 7 - 2br, Waterfront

Bungalow 7 - 2br, Waterfront
3.0 star property
Westhampton Beach
Bungalow 7 - 2br, Waterfront
A wooden pathway flanked by stone walls and dense greenery, leading towards a building with a visible window.

14. Bungalow 5 - 1br, Water View

Bungalow 5 - 1br, Water View
3.0 star property
Westhampton Beach
Bungalow 5 - 1br, Water View

15. Pristine on Bishops Pond

Pristine on Bishops Pond
3.5 star property
Southampton
Pristine on Bishops Pond

16. Hampton Bay Village Beauty

Hampton Bay Village Beauty
3.5 star property
Hampton Bays
Hampton Bay Village Beauty
A spacious room with a high ceiling, a large window, and a cozy seating area with a sofa and chairs.

17. Sugar Loaf Serenity

Sugar Loaf Serenity
4.0 star property
Southampton
Sugar Loaf Serenity

18. Coves Bay Beauty

Coves Bay Beauty
4.0 star property
Sag Harbor
Coves Bay Beauty

19. Sandpiper Seclusion

Sandpiper Seclusion
3.5 star property
Bridgehampton
Sandpiper Seclusion

20. Sagaponack Seclusion

Sagaponack Seclusion
2.0 star property
Sagaponack
Sagaponack Seclusion
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 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
Accommodation
70 Holiday Homes
Lowest Price
Highest Price