Village of Southampton Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Village of Southampton

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

Holiday 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!!!🏖️

Holiday 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

Holiday Home in Southampton

10.0 out of 10, Exceptional, (3)
"perfect for families"
United States
Okito H.
The price is HK$3,503
HK$8,637 total
includes taxes & fees
3 Dec - 4 Dec
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

Holiday 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

Holiday 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

Holiday 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 HK$3,114
HK$5,844 total
includes taxes & fees
29 Dec - 30 Dec
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

Holiday 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

Holiday 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

Holiday 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 HK$2,404
HK$5,174 total
includes taxes & fees
3 Dec - 4 Dec
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Pool
10 Bedroom Hampton House with a regulation size Pickleball court

Holiday 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!

Holiday 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

Holiday 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

Holiday Home in Hampton Bays

10.0 out of 10, Exceptional, (12)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is HK$973
HK$9,651 total
includes taxes & fees
17 Dec - 18 Dec
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Outdoor pool, a heated pool
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Holiday 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

Holiday 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

Holiday 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 traveller
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

Holiday 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

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Clean and quiet."
Christopher 2-night trip
Posted 2 days ago
The Bentley Hotel Southampton

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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  • Enter your travel dates to view the best deals on holiday rentals in Village of Southampton while they last

Look no further and take a look at our great range of rental properties in Village of Southampton!

Frequently asked questions

Are there holiday rentals in Village of Southampton?

Yes, there are holiday rentals close to the most popular sights in Village of Southampton, or you can select a more secluded option if you're looking for a relaxing stay. Village of Southampton is known for its churches and monuments. Make sure you have time to check out the theatres and entertainment choices during your trip.

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

With 127 Expedia holiday rentals, you're guaranteed 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 holiday rental in Village of Southampton like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Village of Southampton. Holiday rentals provide amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.