Town of Southampton Holiday Rentals

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Top cities in Town of Southampton

A pebbled beach at sunset with the sun setting over the horizon.
Vacation Rentals

Riverhead

Riverhead

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Town of Southampton holiday rentals

A single-story house with a gabled roof, a front porch, and a well-maintained garden.

1. Walk to Beach | Seabreeze Cottage #4

Walk to Beach | Seabreeze Cottage #4
Hampton Bays
8.8 out of 10, Excellent, (9 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is AU$689
includes taxes & fees
30 Nov - 1 Dec
Walk to Beach | Seabreeze Cottage #4
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, (21 reviews)
"What an amazing view!!!!! Great place to stay!!! Highly recommend the Black Swan home."
United States
John M.
The price is AU$1,735
includes taxes & fees
10 Nov - 11 Nov
Beachfront Jacuzzi All Year - Black Swan Home
A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

3. 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, (7 reviews)
"This was a great property. Very convenient to where we like to visit. It really had everything we needed for a great weeks stay."
United States
Sherri K.
The price is AU$463
includes taxes & fees
9 Dec - 10 Dec
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
A hot tub with a checkered roof structure and surrounding greenery.

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$1,643
includes taxes & fees
10 Nov - 11 Nov
Jacuzzi year-round - Villa Luz Private Home
A brick patio with outdoor seating, a wooden staircase, and a house with a window and door.

5. Cozy Cottage by the beach - Seabreeze #1

Cozy Cottage by the beach - Seabreeze #1
Hampton Bays
The price is AU$635
includes taxes & fees
16 Nov - 17 Nov
Cozy Cottage by the beach - Seabreeze #1
A small cabin with a porch, surrounded by trees and a fenced area.

6. 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$709
includes taxes & fees
10 Nov - 11 Nov
Lovely studio with AC in charming Sag Harbor
Terrace/patio

7. Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage

Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is AU$577
includes taxes & fees
18 Nov - 19 Nov
Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage
A cozy room with a white sofa, a small table, and a window with blinds.

8. 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$833
includes taxes & fees
10 Nov - 11 Nov
Prime location, walk to all, cozy cottage Westhampton Beach
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

9. 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$779
includes taxes & fees
10 Nov - 11 Nov
Immaculate Waterfront 2 bedroom!
A house with a sliding glass door, a white door, and a small porch with potted plants.

10. 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$1,611
includes taxes & fees
10 Nov - 11 Nov
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A modern living room with a wooden accent wall, a flat-screen TV, a fireplace, and a dining area with a chair and table.

11. 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$803
includes taxes & fees
15 Nov - 16 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

12. 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$1,528
includes taxes & fees
10 Nov - 11 Nov
Minutes from the beach, brand new 4 bedroom
A modern living room with a sofa, armchairs, a coffee table, and a TV.

13. 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$1,608
includes taxes & fees
10 Nov - 11 Nov
Minutes from the beach, brand new 3 bedroom
A living room with a dining area, a sofa, a bench, and a TV.

14. Luxury Village Rental in the Heart of Sag Harbor

Luxury Village Rental in the Heart of Sag Harbor
Sag Harbor
The price is AU$1,187
includes taxes & fees
10 Nov - 11 Nov
Luxury Village Rental in the Heart of Sag Harbor
A modern living room with a grey sofa, round coffee table, and a white fireplace.

15. 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$3,683
includes taxes & fees
10 Nov - 11 Nov
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
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$4,136
includes taxes & fees
10 Nov - 11 Nov
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
A modern kitchen with white cabinets, a dining area with a round table, and a living area with a sofa and decorative pillows.

17. 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$2,083
includes taxes & fees
10 Nov - 11 Nov
Cozy Hamptons Escape 3BR Minutes From Beach!
A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

18. 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$2,061
includes taxes & fees
10 Nov - 11 Nov
Newly Renovated Pristine Southampton Colonial
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$2,397
includes taxes & fees
10 Nov - 11 Nov
Elegant 5-Bedroom Hamptons Home with Private Pool
A dining area with a round table and chairs, surrounded by bookshelves filled with books and decorative items.

20. 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)
"A great place to stay in Southampton!"
United States
Sarah
The price is AU$4,049
includes taxes & fees
10 Nov - 11 Nov
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
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

A reception area with a marble counter, wooden walls, and a large vertical sign for The Preston House & Hotel.
The Preston House & Hotel

The Preston House & Hotel

The Preston House & Hotel
Riverhead

10/10 Excellent

Fantastic stay at the Preston House and Hotel. From the moment we checked in until the morning we checked out we could not fault this hotel. Great stay with friendly and helpful staff.
Australia
Peter
Reviewed March 31, 2024
The Preston House & Hotel

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$463 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.