Southampton Vacation Rentals from $587: Search Short-Term Rentals

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Our top choices for Southampton vacation rentals

A covered patio with a table and chairs, large windows, and a view of greenery.

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

Southampton

Angelo D.

$514 nightly

Oct 4 - Oct 5

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.

$971 nightly

Oct 4 - Oct 5

Total with taxes and fees

A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

3. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Southampton

Justin

$836 nightly

Oct 21 - Oct 22

Total with taxes and fees

A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

4. Amazing Southampton Home with Private Heated Pool

Southampton

Serina R.

$1,464 nightly

Oct 26 - Oct 27

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

$2,570 nightly

Oct 4 - Oct 5

Total with taxes and fees

A wooden gate partially covered by lush green ivy.

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

Southampton

Deborah V.

$2,584 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

7. Newly Renovated Pristine Southampton Colonial

Southampton

Brian M.

$2,621 nightly

Oct 2 - Oct 3

Total with taxes and fees

A spacious living room with a large sofa, a round coffee table, and a television. A kitchen with a refrigerator and cabinets is visible in the background.

8. 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

$436 nightly

Oct 4 - Oct 5

Total with taxes and fees

A modern building with large windows overlooking a beach.

9. Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

Donald J.

$1,171 nightly

Oct 12 - Oct 13

Total with taxes and fees

A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

10. Jacuzzi year-round - Villa Luz Private Home

Hampon Bays

Annie B.

$1,584 nightly

Oct 4 - Oct 5

Total with taxes and fees

A driveway with a parked car, surrounded by trees and illuminated pathway lights.

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

Bridgehampton

Robert R.

$532 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

12. Charming Accommodations in the Hamptons

Sag Harbor

$446 nightly

Oct 5 - Oct 6

Total with taxes and fees

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

13. Immaculate Waterfront 2 bedroom!

Hampton Bays

Michael L.

$503 nightly

Oct 8 - Oct 9

Total with taxes and fees

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

14. North Fork Resort

Greenport

Harold

$222 nightly

Oct 4 - Oct 5

Total with taxes and fees

15. Windward Shores Ocean Resort

Napeague

Gaurang J

$143 nightly

Oct 15 - Oct 16

Total with taxes and fees

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

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

Flanders

James W.

$279 nightly

Oct 6 - Oct 7

Total with taxes and fees

A tent with a wooden frame, two red chairs, and a table.

17. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

East Hampton

Christina V.

$260 nightly

Oct 2 - Oct 3

Total with taxes and fees

18. Cliffside Resort Condominiums

Greenport

Christine

$266 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

19. Elegant 5-Bedroom Hamptons Home with Private Pool

Hampton Bays

Sarah A.

$857 nightly

Oct 4 - Oct 5

Total with taxes and fees

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

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

Sag Harbor

maria m.

$975 nightly

Oct 2 - Oct 3

Total with taxes and fees

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Top Southampton Hotel Reviews

Southampton Inn

8/10 Good

"The check-in date of 4PM in the afternoon was a turn off given you are paying foe the full day. Bit of a money grab. Further the gentleman at the front desk who checked us in when we got there was arrogant. Otherwise a nice stay."

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."

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!"

Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa

10/10 Excellent

"We had a great stay at this house. This was our 3rd year doing this and by far the favorite house of my family. (3 adult kids plus sig others.) The deck and pool space were really comfortable and we used them a lot. The gym and sauna were huge bonuses that were also a big hit. I've actually rented in this area before and I really like the neighborhood. We would definitely consider renting this house next year, depending on our availability around this time of summer. Thanks to the owners for providing fun way to end the summer."

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

10/10 Excellent

"We did a large family trip to the Hamptons for Labor Day weekend 2026. It was a bucket list trip and the house well exceeded our expectations! It was plenty big and fit our group nicely. We also really enjoyed the location, the large yard and pool. It's a short walk to the water and a quick drive to get into Sag Harbor. The host was great and responded to all of our questions. The check-in, check-out process was also super easy. Highly recommend. We hope to book again in the coming years!"

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 $587 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. Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

2. Minutes from the beach, brand new 4 bedroom

3. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

4. Amazing Southampton Home with Private Heated Pool

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

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

7. Newly Renovated Pristine Southampton Colonial

8. Steps to the beach | Seabreeze Cottage #3

9. Beachfront Jacuzzi All Year - Black Swan Home

10. Jacuzzi year-round - Villa Luz Private Home

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

12. Charming Accommodations in the Hamptons

13. Immaculate Waterfront 2 bedroom!

14. North Fork Resort

15. Windward Shores Ocean Resort

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

17. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

18. Cliffside Resort Condominiums

19. Elegant 5-Bedroom Hamptons Home with Private Pool

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

Find vacation rentals that suit your style

Top Southampton Hotel Reviews

Southampton Inn

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