Southampton Vacation Rentals from $1,055: Search Short-Term Rentals

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Our top choices for Southampton vacation rentals

A modern living room with a sofa, armchairs, a coffee table, and a TV.

1. Minutes from the beach, brand new 3 bedroom

Southampton

Kathy B.

$932 nightly

Nov 5 - Nov 6

Total with taxes and fees

A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

2. Minutes from the beach, brand new 4 bedroom

Southampton

Okito H.

$923 nightly

Nov 5 - Nov 6

Total with taxes and fees

A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

3. Newly Renovated Pristine Southampton Colonial

Southampton

Brian M.

$1,280 nightly

Nov 5 - Nov 6

Total with taxes and fees

A wooden gate partially covered by lush green ivy.

4. Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Southampton

Sarah

$2,390 nightly

Nov 5 - Nov 6

Total with taxes and fees

A wooden house with a front porch, white railings, and a double door.

5. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

Southampton

Melissa

$2,329 nightly

Nov 8 - Nov 9

Total with taxes and fees

A beach with footprints leading to the water, a sunset in the background, and a clear sky.

6. Steps to the beach | Seabreeze Cottage #3

Hampton Bays

"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...

Lydia

$453 nightly

Nov 30 - Dec 1

Total with taxes and fees

A modern building with large windows overlooking a beach.

7. Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

John M.

$1,214 nightly

Nov 8 - Nov 9

Total with taxes and fees

A hot tub with a checkered roof structure and surrounding greenery.

8. Jacuzzi year-round - Villa Luz Private Home

Hampon Bays

Annie B.

$1,645 nightly

Nov 5 - Nov 6

Total with taxes and fees

9. Walk to Beach | Seabreeze Cottage #4

Hampton Bays

Weston B.

$453 nightly

Nov 30 - Dec 1

Total with taxes and fees

A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

10. Charming Accommodations in the Hamptons

Sag Harbor

$414 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

Katie B.

$466 nightly

Nov 8 - Nov 9

Total with taxes and fees

12. Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage

Hampton Bays

$354 nightly

Nov 12 - Nov 13

Total with taxes and fees

A balcony with a view of the ocean, a lawn, and a house in the background.

13. Cliffside Resort Condominiums

Greenport

William

$269 nightly

Nov 30 - Dec 1

Total with taxes and fees

A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

14. Immaculate Waterfront 2 bedroom!

Hampton Bays

Michael L.

$478 nightly

Nov 5 - Nov 6

Total with taxes and fees

A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

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

Flanders

Sherri K.

$282 nightly

Dec 1 - Dec 2

Total with taxes and fees

A modern house with a deck, outdoor seating, and a fire pit.

16. North Fork Resort

Greenport

Altynai

$296 nightly

Nov 8 - Nov 9

Total with taxes and fees

A small cabin with a porch, surrounded by trees and a fenced area.

17. Lovely studio with AC in charming Sag Harbor

Sag Harbor

"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...

Emily t.

$435 nightly

Nov 5 - Nov 6

Total with taxes and fees

18. Windward Shores Ocean Resort

Napeague

Banessa

$156 nightly

Nov 18 - Nov 19

Total with taxes and fees

A backyard with a swimming pool, wicker lounge chairs, and potted plants.

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

Sag Harbor

maria m.

$949 nightly

Nov 5 - Nov 6

Total with taxes and fees

A dining area with a round table, six chairs, and a chandelier.

20. Year round Jacuzzi - Blackberry East Hampton Home

East Hampton

Suzanne R.

$1,251 nightly

Nov 8 - Nov 9

Total with taxes and fees

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Top Southampton Hotel Reviews

Hamlet Inn

10/10 Excellent

"Very nice accommodations and friendly staff. Check-in is easy and drive up to the individual units is very convenient. The room was very clean and well appointed. The heat and water worked well."

Quintessential Hamptons 6 BR Home with Outdoor Thermasol Sauna, In-Ground...

10/10 Excellent

"I booked The Manor for a special long weekend with family and couldnt have asked for a better place to stay! The Manor has the perfect layout for hosting a large group, there is plenty of seating together, and plenty of seating separate if you want some space. The decor and amenities are wonderful as well. During my stay, we unfortunately didnt have the best weather, that being said we still had a great time at The Manor, and can only imagine how much more wonderful it is with nice weather. I couldnt recommend The Manor more and hope to return. Thanks for a great stay!"

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

10/10 Excellent

"My wife and I were in town for a wedding. Michael was very nice and professional. Met us in the driveway and gave us the lay of the land. The unit was clean and had everything to you would need. Great location within walking distance of town. Would go back and stay again."

Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts

10/10 Excellent

"Loved this home- it was a perfect place for our group of 7 adults! Plenty of comfortable space to sit and talk, both inside and out. Rooms were spacious and comfortable! Check in and check out had limited instructions, which was a bit unusual based on prior experiences, but everything was simple enough. Host was responsive to questions through the app. Overall would recommend and would stay again!"

Find out more about Southampton

Everything you need to know about Southampton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southampton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Southampton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southampton vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $1,055 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southampton rentals

At Expedia, we put the best Southampton vacation 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 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 Southampton vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around 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.

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Things to do in Southampton

Frequently asked questions

Can I find vacation rentals in Southampton?

Yes, you can find vacation rentals in Southampton close to Southampton Arts Center, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Southampton. Make sure you have time to check out the museums and festivals during your trip.

What are some of the best vacation rentals in Southampton?

Private 2.1 acre gated home with heated pool and tennis & pickleball court: Visitors like this Southampton vacation home rental. It is located near the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and an arcade game room so you can immerse yourself in your vacation. Some other top choices in Southampton are Spacious Southampton Home in Shinnecock Hills, Central Between Southampton,... and Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping.

How many vacation rentals are there in Southampton?

Expedia has 481 vacation rentals for your stay in Southampton.

What can I see and do in Southampton?

Enjoy the outdoors at Cooper's Beach and The Hamptons Beaches, or simply take in cultural attractions like Southampton Historical Museum and Halsey House. Other places in town to visit include Southampton Arts Center and Shinnecock Hills Golf Course.

What are vacation rentals like in Southampton?

Vacation rentals are private properties you can reserve for a short or long stay in Southampton. Vacation rentals feature amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.

Southampton Vacation Rentals

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Check prices for these dates

Our top choices for Southampton vacation rentals

1. Minutes from the beach, brand new 3 bedroom

2. Minutes from the beach, brand new 4 bedroom

3. Newly Renovated Pristine Southampton Colonial

4. Contemporary Southampton Village Home Walking Distance to Town, Pool,...

5. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

6. Steps to the beach | Seabreeze Cottage #3

7. Beachfront Jacuzzi All Year - Black Swan Home

8. Jacuzzi year-round - Villa Luz Private Home

9. Walk to Beach | Seabreeze Cottage #4

10. Charming Accommodations in the Hamptons

11. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

12. Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage

13. Cliffside Resort Condominiums

14. Immaculate Waterfront 2 bedroom!

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

16. North Fork Resort

17. Lovely studio with AC in charming Sag Harbor

18. Windward Shores Ocean Resort

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

20. Year round Jacuzzi - Blackberry East Hampton Home

Find vacation rentals that suit your style

Top Southampton Hotel Reviews

Hamlet Inn

Find out more about Southampton

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