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

Town of Southampton Holiday Rentals

  • 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

Top Cities in Town of Southampton

A wooden dock with bicycles parked on it.
Holiday RentalsHoliday Rentals

Westhampton Beach

Westhampton Beach

Our top choices for Town of Southampton holiday rentals

A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

1. 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 AU$1,355
includes taxes & fees
27 Sept - 28 Sept
Elegant 5-Bedroom Hamptons Home with Private Pool
A modern building with large windows overlooking a beach.

2. 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 AU$1,699
includes taxes & fees
27 Sept - 28 Sept
Beachfront Jacuzzi All Year - Black Swan Home
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

3. 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$1,301
includes taxes & fees
26 Sept - 27 Sept
Immaculate Waterfront 2 bedroom!
A modern kitchen with white cabinets, a dining area with a round table, and a living area with a sofa and decorative pillows.

4. 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$1,801
includes taxes & fees
26 Sept - 27 Sept
Cozy Hamptons Escape 3BR Minutes From Beach!
A covered patio with a table and chairs, large windows, and a view of greenery.

5. Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Southampton
9.6 out of 10, Exceptional, (10 reviews)
"Very nice place and super responsive host. "
United States
Angelo D.
The price is AU$827
includes taxes & fees
27 Sept - 28 Sept
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
A modern living room with a sofa, armchairs, a coffee table, and a TV.

6. Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
10.0 out of 10, Exceptional, (4 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$1,981
includes taxes & fees
27 Sept - 28 Sept
Minutes from the beach, brand new 3 bedroom
A modern living room with a grey sofa, round coffee table, and a white fireplace.

7. 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 AU$3,763
includes taxes & fees
26 Sept - 27 Sept
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

8. 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 AU$903
includes taxes & fees
11 Oct - 12 Oct
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A small cabin with a porch, surrounded by trees and a fenced area.

9. Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
6.0 out of 10, (1 review)
"For a last minute trip, we couldn't beat the location. Less than 10 minutes from Sag Harbor and Bridgehampton main streets as well as from Sagaponack beaches. The space is quaint and offers everything you need, a small kitchenette, a work desk, outdoor space. There was several communications sent regarding privacy and not interacting with other guests on property which I can appreciate but felt excessive.My two biggest complaints and likely why I would not rebook was first the cleanliness of the...
United States
Emily t.
The price is AU$773
includes taxes & fees
27 Sept - 28 Sept
Lovely studio with AC in charming Sag Harbor
A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

10. 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$3,780
includes taxes & fees
28 Sept - 29 Sept
Newly Renovated Pristine Southampton Colonial
A compact laundry room with a washing machine, a dryer, and a small sink area.

11. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
The price is AU$1,904
includes taxes & fees
18 Oct - 19 Oct
Lovely & Spacious Sag Harbor escape with heated pool
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

12. 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$1,323
includes taxes & fees
21 Oct - 22 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

13. 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$2,312
includes taxes & fees
27 Sept - 28 Sept
Jacuzzi year-round - Villa Luz Private Home
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

14. 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$2,037
includes taxes & fees
1 Oct - 2 Oct
Minutes from the beach, brand new 4 bedroom
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

15. Walk to Beach | Seabreeze Cottage #4

Walk to Beach | Seabreeze Cottage #4
Hampton Bays
8.6 out of 10, Excellent, (8 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is AU$602
includes taxes & fees
27 Sept - 28 Sept
Walk to Beach | Seabreeze Cottage #4
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 AU$5,028
includes taxes & fees
4 Oct - 5 Oct
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

17. 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.
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

18. 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, (2 reviews)
"Adorable cottage in a perfect location to walk into West Hampton town and the beaches. Easy check-in with great communication. Plenty of amenities, including bikes, beach chairs, towels, and all you need to have a BBQ. Peaceful backyard - perfect to relax and read or enjoy an outside BBQ with family. I was with 2 girls friends and it was great for our needs."
United States
Cindy M.
The price is AU$902
includes taxes & fees
2 Oct - 3 Oct
Prime location, walk to all, cozy cottage Westhampton Beach
A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

19. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (6 reviews)
"The host was very welcoming and the house was very clean"
United States
James W.
The price is AU$465
includes taxes & fees
5 Oct - 6 Oct
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
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

Hamlet Inn

Hamlet Inn

10/10 Excellent
"The hotel location is ideal. About a 2 mile radius from the town center, shopping, attractions and beaches. The room is very comfortable where all necessary amenity items are available. We had a nice closet in the room, a refrigerator and microwave. It would have been nice to have a couple of drawers if we had stayed more than 2 nights. The shower was particularly nice! Coffe, tea, soft drinks along with a wide variety of snacks, cakes and candy bars are available the entire day."
Niel 2-night trip
Posted 3 days ago
Hamlet Inn

Find out more about Town of Southampton

Everything you need to know about Town of Southampton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Town of Southampton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Town of Southampton holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Town of Southampton holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Town of Southampton. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Town of Southampton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Town of Southampton holiday rentals we have chosen for you start as low as AU$2,037 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Town of Southampton rentals

At Expedia, we put the best Town of Southampton holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Town of Southampton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Town of Southampton holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Town of Southampton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.