Village of Southampton Vacation Rentals

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Check prices for these dates

Tonight
Dec 2 - Dec 3
Tomorrow
Dec 3 - Dec 4
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Vacation Rentals in Village of Southampton

Terrace/patio
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...

Vacation Home in Southampton

9.8 out of 10, Exceptional, (18)
"This place was the perfect home away from home during the holidays. My family enjoyed their stay and we’d all definitely recommend this place for larger parties."
United States
Casey And Maria
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Outdoor dining
Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

Vacation Home in Southampton

10.0 out of 10, Exceptional, (109)
"Beautiful property and an amazing host."
United States
Patrick B.
Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️
Fridge, microwave, oven, stovetop
Minutes from the beach, brand new 4 bedroom

Vacation Home in Southampton

10.0 out of 10, Exceptional, (3)
"perfect for families"
United States
Okito H.
The price is ￥70,002
￥172,574 total
includes taxes & fees
Dec 4 - Dec 5
Minutes from the beach, brand new 4 bedroom
Beach nearby
Cliffside Resort Condominiums

Aparthotel in Greenport

3.0 star property
9.0 out of 10, Wonderful, (249)
"Great stay - beautiful place"
United States
Rebecca
Cliffside Resort Condominiums
Fridge, microwave, oven, stovetop
STUNNING LUXURY HOME ~ PRIVATE POOL/HOT TUB ~ PERFECT HAMPTONS GETAWAY ~ MBH

Vacation Home in East Hampton

9.6 out of 10, Exceptional, (39)
"Beautiful house! Great area! Great host!"
United States
brooke v.
STUNNING LUXURY HOME ~ PRIVATE POOL/HOT TUB ~ PERFECT HAMPTONS GETAWAY ~ MBH
Outdoor pool, a heated pool
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Vacation Home in Westhampton Beach

10.0 out of 10, Exceptional, (195)
"My family and I thoroughly enjoyed our stay! The house is very spacious and the outdoor area/pool are beautiful. Check-in was a breeze and the host was very friendly and responsive to all our questions about the home as well as offering wonderful suggestions for restaurants and beaches in the area. Would definitely recommend for a family vacation!"
United States
livinann
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Smart TV, fireplace, stereo
Mid-Century Home with Pool, Private Beach Access, and Long-Stay Summer Savings

Vacation Home in East Hampton

10.0 out of 10, Exceptional, (95)
"Great stay and great communication! "
United States
Nicole S.
Mid-Century Home with Pool, Private Beach Access, and Long-Stay Summer Savings
Smart TV, fireplace, video games, stereo
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

Cottage in Center Moriches

10.0 out of 10, Exceptional, (110)
"Amazing stay! Everything was super clean and beautiful "
United States
Liannys P.
The price is ￥62,224
￥116,770 total
includes taxes & fees
Dec 29 - Dec 30
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
TV, fireplace, video library, stereo
Stunning Hampton Holiday Family Fantasy for your Team

Vacation Home in East Hampton

9.8 out of 10, Exceptional, (74)
"Outstanding house, beautifully maintained and well stocked, with great location."
United States
Jason C.
Stunning Hampton Holiday Family Fantasy for your Team
Outdoor pool, a heated pool
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Vacation Home in Sag Harbor

10.0 out of 10, Exceptional, (89)
"House that has everything you need for a wonderful getaway! Excellent communication with the property owner. Thank you Jay for everything and your hospitality! "
United States
Maria R.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Oven, stovetop, dishwasher
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Vacation Home in Calverton

2.0 star property
8.6 out of 10, Excellent, (8)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
The price is ￥48,029
￥103,393 total
includes taxes & fees
Dec 4 - Dec 5
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Pool
10 Bedroom Hampton House with a regulation size Pickleball court

Vacation Home in Hampton Bays

10.0 out of 10, Exceptional, (32)
"Location of this property is impeccable."
United States
Stephen M.
10 Bedroom Hampton House with a regulation size Pickleball court
Outdoor dining
Cozy Hamptons Beach House 1 Block from the Beach!

Vacation Home in Montauk

9.6 out of 10, Exceptional, (4)
"Great location between Montauk and East Hampton, easy to go between both. Great access to the beach."
United States
Andrew F.
Cozy Hamptons Beach House 1 Block from the Beach!
Terrace/patio
Charming 4-bedroom house with salt water pool, AC and WiFi in Hampton Bays

Vacation Home in Hampton Bays

10.0 out of 10, Exceptional, (1)
"Awesome house, very convenient to the beach and town. Beautiful yard and pool for grilling and hanging. Would love to come back again!"
United States
Brendan O.
Charming 4-bedroom house with salt water pool, AC and WiFi in Hampton Bays
Terrace/patio
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Vacation Home in Hampton Bays

9.6 out of 10, Exceptional, (13)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is ￥19,445
￥192,835 total
includes taxes & fees
Dec 8 - Dec 9
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Outdoor pool, a heated pool
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Vacation Home in Southampton

9.8 out of 10, Exceptional, (32)
"This place was so nice and so close to so many fun places! "
United States
Daniella L.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Fridge, microwave, oven, stovetop
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Vacation Home in Eastport

9.6 out of 10, Exceptional, (34)
"We had a amazing stay and plan to come back next July again"
United States
Gina G.
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
Outdoor pool, a heated pool
A Quiet Place in the Hamptons

Vacation Home in East Quogue

9.6 out of 10, Exceptional, (38)
"Fantastic house for the extended family ! We loved the pool , enjoyed bbq grilling and hanging out together! "
United States
Anonymous traveler
A Quiet Place in the Hamptons
Terrace/patio
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Camping in East Hampton

8.6 out of 10, Excellent, (4)
"Had a nice peaceful evening eating our pizza and relaxing while watching the sunset. Nice way to celebrate our 30th, back to the woods❤️"
United States
Ellen
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
A heated pool
Brand New in the Heart of East Hampton Village with Pool

Vacation Home in East Hampton

10.0 out of 10, Exceptional, (33)
"Excellent location, beautiful home and great communication "
United States
Robin S.
Brand New in the Heart of East Hampton Village with 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

Southampton Inn

Southampton Inn

10/10 Excellent
"Very clean and nice room"
Elie 2-night trip
Posted 8 days ago
Southampton Inn

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 near top sights in Village of Southampton, or you can select a more secluded option if you're looking for relaxation. 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?

9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub: This vacation home rental near Village of Southampton is located by the ocean and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 9 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 garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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

With 127 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.