Southampton Vacation Rentals from ￥92,440: 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.

￥92,440 total

includes taxes & fees

Oct 4 - Oct 5

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

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

Southampton

Justin

￥150,311 total

includes taxes & fees

Oct 21 - Oct 22

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

3. Minutes from the beach, brand new 3 bedroom

Southampton

Kathy B.

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

4. Minutes from the beach, brand new 4 bedroom

Southampton

Okito H.

￥170,627 total

includes taxes & fees

Oct 14 - Oct 15

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

5. Amazing Southampton Home with Private Heated Pool

Southampton

Serina R.

￥259,048 total

includes taxes & fees

Oct 26 - Oct 27

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

6. Newly Renovated Pristine Southampton Colonial

Southampton

Brian M.

￥460,113 total

includes taxes & fees

Oct 14 - Oct 15

A wooden gate partially covered by lush green ivy.

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

Southampton

Deborah V.

￥574,241 total

includes taxes & fees

Oct 14 - Oct 15

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

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

Southampton

Melissa

￥448,637 total

includes taxes & fees

Oct 14 - Oct 15

A tented accommodation with two beds, a small table, a chair, and a cabinet.

9. Safari Tent Glamping,D27-CedarPt, East Hampton, NY

East Hampton

Brian

￥48,816 total

includes taxes & fees

Oct 1 - Oct 2

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.

10. 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

￥73,160 total

includes taxes & fees

Oct 14 - Oct 15

11. Windward Shores Ocean Resort

Napeague

Gaurang J

￥25,665 total

includes taxes & fees

Oct 18 - Oct 19

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

￥94,574 total

includes taxes & fees

Oct 13 - Oct 14

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

Hampon Bays

Annie B.

￥263,242 total

includes taxes & fees

Oct 14 - Oct 15

A modern building with large windows overlooking a beach.

14. Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

Donald J.

￥194,645 total

includes taxes & fees

Oct 13 - Oct 14

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

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

East Hampton

Christina V.

￥46,825 total

includes taxes & fees

Oct 2 - Oct 3

16. Cliffside Resort Condominiums

Greenport

Christine

￥59,874 total

includes taxes & fees

Oct 25 - Oct 26

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

17. North Fork Resort

Greenport

Harold

￥45,770 total

includes taxes & fees

Oct 13 - Oct 14

18. Driftwood Resort

Montauk

William

￥26,221 total

includes taxes & fees

Oct 7 - Oct 8

A spacious living area with a large bed, a dining table, and a kitchen in the background.

19. Unit 1021: Studio | 2nd Floor-Pool View | Starfish

Napeague

Liana T.

￥77,705 total

includes taxes & fees

Oct 6 - Oct 7

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

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

Flanders

James W.

￥50,843 total

includes taxes & fees

Oct 6 - Oct 7

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Top Southampton Hotel Reviews

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."

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!"

Minutes from the beach, brand new 4 bedroom

10/10 Excellent

"Great rental property close to Southampton town. Easy access to Route 27. Walking distance to Tate’s (10 minutes) and downtown (15-20 minutes). 10-12 minute drive to Coopers Beach. House was clean, updated, and well supplied. Having two en-suite king rooms is a real plus as well. Fenced in backyard great for traveling with pets. Would not hesitate to stay again."

Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

8/10 Good

"Ken was a good host: readily available and communicated well.The property was as advertised. We were a group of college buddies getting together nearly 40 years after graduation. This secluded retreat was ideal for us. The rustic property was clean. There were more than enough beds for our small group of six."

Find out more about Southampton

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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.

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

3. Minutes from the beach, brand new 3 bedroom

4. Minutes from the beach, brand new 4 bedroom

5. Amazing Southampton Home with Private Heated Pool

6. Newly Renovated Pristine Southampton Colonial

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

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

9. Safari Tent Glamping,D27-CedarPt, East Hampton, NY

10. Steps to the beach | Seabreeze Cottage #3

11. Windward Shores Ocean Resort

12. Charming Accommodations in the Hamptons

13. Jacuzzi year-round - Villa Luz Private Home

14. Beachfront Jacuzzi All Year - Black Swan Home

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

16. Cliffside Resort Condominiums

17. North Fork Resort

18. Driftwood Resort

19. Unit 1021: Studio | 2nd Floor-Pool View | Starfish

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

Find vacation rentals that suit your style

Top Southampton Hotel Reviews

Hamlet Inn

5BR, Luxury Home, Pool, Large Yard , Close to Beach & Town

Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!⛱️

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

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

Capri

Sea Haven Resort Motel

Minutes from the beach, brand new 4 bedroom

Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

Find out more about Southampton

Frequently asked questions

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