A wooden boardwalk leading through tall grass towards a body of water.

Village of Southampton Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Village of Southampton vacation rentals

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

1. 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 ￥71,033
￥175,115 total
includes taxes & fees
Oct 6 - Oct 7
Minutes from the beach, brand new 4 bedroom
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!

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 ￥24,861
￥92,246 total
includes taxes & fees
Oct 5 - Oct 6
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A wooden gate partially covered by lush green ivy.

3. 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 ￥336,757
￥443,205 total
includes taxes & fees
Nov 1 - Nov 2
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
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.

4. Steps to the beach | Seabreeze Cottage #3

Steps to the beach | Seabreeze Cottage #3
Hampton Bays
6.0 out of 10, (3 reviews)
"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...
United States
Lydia
The price is ￥9,482
￥68,228 total
includes taxes & fees
Oct 5 - Oct 6
Steps to the beach | Seabreeze Cottage #3
Room

5. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (324 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is ￥18,776
￥25,744 total
includes taxes & fees
Oct 12 - Oct 13
Windward Shores Ocean Resort
A modern building with large windows overlooking a beach.

6. 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 ￥17,837
￥189,120 total
includes taxes & fees
Oct 5 - Oct 6
Beachfront Jacuzzi All Year - Black Swan Home
A covered patio with a table and chairs, large windows, and a view of greenery.

7. 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 ￥55,311
￥92,804 total
includes taxes & fees
Oct 4 - Oct 5
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

8. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is ￥35,516
￥80,432 total
includes taxes & fees
Oct 6 - Oct 7
Charming Accommodations in the Hamptons
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

9. 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 ￥17,679
￥264,960 total
includes taxes & fees
Oct 5 - Oct 6
Jacuzzi year-round - Villa Luz Private Home
A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

10. 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 ￥22,730
￥50,137 total
includes taxes & fees
Oct 14 - Oct 15
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
A modern house with a deck, outdoor seating, and a fire pit.

11. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (62 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is ￥39,249
￥44,843 total
includes taxes & fees
Oct 12 - Oct 13
North Fork Resort
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

12. 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 ￥44,987
￥92,697 total
includes taxes & fees
Nov 1 - Nov 2
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

13. 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 ￥42,620
￥90,715 total
includes taxes & fees
Oct 8 - Oct 9
Immaculate Waterfront 2 bedroom!
Terrace/patio

14. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (295 reviews)
"Great place!"
United States
Christine
The price is ￥26,681
￥47,996 total
includes taxes & fees
Nov 1 - Nov 2
Cliffside Resort Condominiums
A tent with a wooden frame, two red chairs, and a table.

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
The price is ￥30,533
￥46,968 total
includes taxes & fees
Oct 4 - Oct 5
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

16. Amazing Southampton Home with Private Heated Pool

Amazing Southampton Home with Private Heated Pool
Southampton
9.0 out of 10, Wonderful, (2 reviews)
"Very cozy house in a great location!"
United States
Serina R.
The price is ￥106,864
￥215,402 total
includes taxes & fees
Oct 20 - Oct 21
Amazing Southampton Home with Private Heated Pool
A wooden house with a front porch, white railings, and a double door.

17. 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 ￥337,452
￥461,006 total
includes taxes & fees
Oct 4 - Oct 5
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
A beach with people relaxing on chairs and sunbathing.

18. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (26 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is ￥14,996
￥40,037 total
includes taxes & fees
Nov 1 - Nov 2
Harbor Heights
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

19. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is ￥14,996
￥39,676 total
includes taxes & fees
Nov 2 - Nov 3
The SandPiper
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

20. 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 ￥71,033
￥154,555 total
includes taxes & fees
Oct 6 - Oct 7
Elegant 5-Bedroom Hamptons Home with Private 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 Village of Southampton Hotel Reviews

Zey Hotel

Zey Hotel

10/10 Excellent
"Our stay was impressive. We hadn't expected how comfortable and roomy the suite was. The whirlpool bath was like a small swimming pool and the room was large enough to have a party."
Neil 1-night trip
Posted 2 hours ago
Zey Hotel

Find out more about Village of Southampton

Search for holiday rentals in Village of Southampton on Expedia! You can easily find your home rentals, villas, holiday apartments in Village of Southampton using one of the methods below:

  • View our selection of featured holiday rentals in Village of Southampton
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Look no further and take a look at our great range of rental properties in Village of Southampton!

Frequently asked questions

Are there vacation rentals in Village of Southampton?

Yes, we offer vacation rentals in Village of Southampton near Southampton Arts Center, or you can select a more secluded option if you'd like a relaxing place to stay. Village of Southampton is known for its churches and monuments. Make sure you have time to check out the theaters and entertainment choices during your trip.

What are some of the best vacation rentals that Village of Southampton has to offer?

Minutes from the beach, brand new 4 bedroom: Visitors like this Village of Southampton vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Village of Southampton?

With 123 Expedia vacation rentals, you're sure to find just the right place for your Village of Southampton stay.

What can I see and do in Village of 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 Southampton Cultural Center.

What’s a vacation rental in Village of Southampton like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Village of Southampton. Vacation rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a family getaway.