Village of Southampton Vacation Rentals

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Vacation Rentals in Village of Southampton

Minutes from the beach, brand new 4 bedroom

The price is CA $1,109
CA $2,171 total
includes taxes & fees
May 1 - May 2
Minutes from the beach, brand new 4 bedroom

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (282)
"Condo was great, family of 5 , clean, no hassle"
The price is CA $198
CA $256 total
includes taxes & fees
Apr 29 - Apr 30
Windward Shores Ocean Resort

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (210)
"The apartment was beautifully decorated and clean. However, the stove did not work, the iron did not work and the TV in the Livingroom did not work."
The price is CA $222
CA $314 total
includes taxes & fees
Apr 30 - May 1
Cliffside Resort Condominiums

Location and views! Located directly on Shinnecock Bay!

9.2 out of 10, Wonderful, (23)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
Location and views! Located directly on Shinnecock Bay!

East End cottage on water!Pet Friendly! Wood FP Minutes from Hamptons & wineries

10.0 out of 10, Exceptional, (86)
"Great property, great views and the owner was terrific in his communication and hospitality.Thank you! "
The price is CA $416
CA $843 total
includes taxes & fees
May 6 - May 7
East End cottage on water!Pet Friendly! Wood FP Minutes from Hamptons & wineries

10 Bedroom Hampton House with a regulation size Pickleball

10.0 out of 10, Exceptional, (25)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball

Mid-Century Modern Beach House: Private Beach, Pool, and Chefs Kitchen

10.0 out of 10, Exceptional, (82)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach, Pool, and Chefs Kitchen

Cozy Hamptons Beach House 1 Block from the Beach!

10.0 out of 10, Exceptional, (1)
"Great location between Montauk and East Hampton, easy to go between both. Great access to the beach."
Cozy Hamptons Beach House 1 Block from the Beach!

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (19)
"Perfect spot for a girls weekend! Property/house as advertised, and the house was fully stocked with all amenities. Thanks for a wonderful stay!! "
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Heated pool fenced in private escape!

9.6 out of 10, Exceptional, (17)
"The house was so nice and private, my friends and I loved it and found it perfect. The pool and hot tub were great and the backyard was gorgeous "
Heated pool fenced in private escape!

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

10.0 out of 10, Exceptional, (6)
"Perfect getaway for a group of ladies spending a snowy night catching up away from our spouses and kids. Cozy fireplace, beautiful home, ample space and in a great location. Highly recommend!"
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!

9.8 out of 10, Exceptional, (17)
"The house was clean and the location was magnificent. Jake was great, offered us early check in and late check out. The neighborhood was lovely, walked my pup and admired all of the beautiful homes. Definitely will stay there again. "
Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!

Recently Renovated and Modernized Hampton Bays Beach Beach Bungalow Perfect...

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great place with great host."
Recently Renovated and Modernized Hampton Bays Beach Beach Bungalow Perfect...

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (67)
"Great home"
Stunning Hampton Holiday Family Fantasy for your Team

A Touch of Ocean Studio, 1 BTH & Balcony Apt!

10.0 out of 10, Exceptional, (5)
"Being literally on the beach with resident access to chairs towels umbrellas and snacks is really awesome."
The price is CA $234
CA $592 total
includes taxes & fees
Apr 29 - Apr 30
A Touch of Ocean Studio, 1 BTH & Balcony Apt!

Gorgeous private Hamptons house with pool and volleyball court

8.4 out of 10, Very good, (17)
"Enjoyed this house in a great location. It was perfect for attending a family wedding!"
Gorgeous private Hamptons house with pool and volleyball court

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!

10.0 out of 10, Exceptional, (41)
"This is the most magical property with a gorgeous pool, beautiful large trees, a pond and a badmitten court. My two children loved it. The property was a 3-4 minute drive from everything and yet felt totally isolated and removed from everything. I will say that the house was more cozy than we expected as the bedrooms upstairs were a steep walk and there was only one bathroom for the entire house. But we made do and had a lovely time."
The price is CA $1,109
CA $1,988 total
includes taxes & fees
Apr 30 - May 1
Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (33)
"We had a great time at the house – it was spacious, clean, and well-maintained. However, after our stay, we realized we had left a winter coat and a blazer. We immediately contacted the property manager, who confirmed they had found our belongings and promised to send them to us. Despite multiple emails and their initial confirmation, they stopped responding and never sent our items. This was very disappointing, especially given the cost of our stay. We’ve rented other properties before, and...
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Newly Renovated, Centrally Located East Hampton Home, Total Privacy,...

10.0 out of 10, Exceptional, (2)
Newly Renovated, Centrally Located East Hampton Home, Total Privacy,...

Magic Place

The price is CA $624
CA $1,259 total
includes taxes & fees
Apr 29 - Apr 30
Magic Place
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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Other types of properties in Village of Southampton you may be interested in

Southampton Inn

3.0 star property
8.6 out of 10, Excellent, (517)
"Perfectly situated in Southampton"
The price is CA $298
CA $363 total
includes taxes & fees
Apr 29 - Apr 30
Southampton Inn

The 1708 House

3.0 star property
10.0 out of 10, Exceptional, (2)
"We absolutely loved our stay here. The house is stunning, the service is fabulous. The best bed ever to sleep in! Great location and a fabulous breakfast. Thank you. "
The 1708 House

Harpoon House

3.0 star property
8.2 out of 10, Very good, (116)
"Place was great! Love the area and place was also very clean and quiet. Great stay and would definitely come back."
The price is CA $476
CA $544 total
includes taxes & fees
Apr 29 - Apr 30
Harpoon House
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.

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.

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

With 131 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.