Village of Southampton Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Holiday Rentals in Village of Southampton

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

10.0 out of 10, Exceptional, (98)
"Pam was very communicative prior to our stay and a welcoming host. The house was clean, centrally located, and spacious. "
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

Beautiful Southampton Village home, new reno, Heated pool!

10.0 out of 10, Exceptional, (33)
"an amazing experience and stay. i booked the house in proximity to the half marathon i was running in. It served well and also a safe haven for my family. looking forward to next year!"
Beautiful Southampton Village home, new reno, Heated pool!

Minutes from the beach, brand new 4 bedroom

The price is AU$2,357
includes taxes & fees
23 Feb - 24 Feb
Minutes from the beach, brand new 4 bedroom

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

9.6 out of 10, Exceptional, (8)
"The house is in a great location but was definitely showing some wear and tear. Things like the pool having damage around the sides, a lot of dishes/cutlery missing, broken glass from prior guests behind chairs, etc. The house could use a walk through with a handyman to fix the issues popping up with fixtures and finishes and a restock on household basics."
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (271)
"Beautiful location, clean property, and nice staff. Just hard to turn in to the parking lot but not much that the hotel can do for that. The private beach is stunning. "
The price is AU$271
includes taxes & fees
20 Mar - 21 Mar
Windward Shores Ocean Resort

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (66)
"Great home"
Stunning Hampton Holiday Family Fantasy for your Team

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

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

10.0 out of 10, Exceptional, (168)
"We had a wonderful stay. The house was great and check in and check out were both easy. We definition would love to stay again."
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (31)
"The mansion is beautiful, with large rooms in the upstairs bedrooms. The 2 bedrooms in the basement were a bit small and a bit Spartan. The fireplace room had 4 remotes, none of which worked the large screen tv, and half of the bedrooms had remotes that did not work the tv's. The kitchen silverware drawer was filthy, requiring my wife to clean the draw and was the silverware. The pocket door in the kitchen was off the track (not a big issue), however it requires repairing, The lower draw in the...
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

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

10.0 out of 10, Exceptional, (5)
"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!"
The price is AU$1,500
includes taxes & fees
24 Feb - 25 Feb
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Summer 2025 Now Available! Wolffer Vineyard Close!

10.0 out of 10, Exceptional, (83)
"Our stay was amazing! The house was fabulous, beautifully appointed, very clean, private and secluded. Lots to do in the area. Jay was very responsive and helpful when we had questions. Would definitely stay again. "
Summer 2025 Now Available! Wolffer Vineyard Close!

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

2.0 star property
7.4 out of 10, Good, (3)
"I had so much fun with my friends"
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

Classic East Hampton 5 BR in Private Beach Community.Pool, HotTub & Pirate Ship

10.0 out of 10, Exceptional, (80)
"The property was exactly as explained and all in our group loved the place. The house was clean and spacious with plenty of space to rekax."
Classic East Hampton 5 BR in Private Beach Community.Pool, HotTub & Pirate Ship

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (127)
"Wonderful throw back beach house..nothing fancy but very comfortable and the views are amazing! Loved spending our Christmas Holiday relaxing by the bay..and the year round hot tub was up and running when we got there! Perfect spot..will definitely go back next year! "
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

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

10.0 out of 10, Exceptional, (18)
"My friends and I stayed at this house for a few days around New Year's. The house is very spacious, and the grounds are lovely. We had a group of 5 and had lots of room to congregate and disappear if we needed alone time. The hot tub was exactly what some of us needed, while the kitchen provided others with much comfort. The one bummer was when we arrived; it looked like someone had just had a party outside so that first made for a bit of cleanup. That little bump shouldn't stop you from...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

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!

Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

10.0 out of 10, Exceptional, (81)
"Very relaxing place to stay 2 minutes from the beach and fabulous sunsets. Property was spotless with tons of room. "
Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

East Hampton Paradise – Cozy 5BR, Pool & Walkable to Beach & Shops

2.0 star property
East Hampton Paradise – Cozy 5BR, Pool & Walkable to Beach & Shops

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

9.4 out of 10, Exceptional, (64)
"We had an incredible time at this house!!! It literally felt like we were staying at a luxury resort and had everything we could have possibly needed for our getaway. Our group included young kids and adults all of whom had an amazing stay. The tennis and basketball court was in great condition and provided endless fun activities. The pool was a great size and the heater worked well when it was needed. There is a ton of space to play sports and games as well as a fire pit which was a great way...
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

STUNNING LUXURY HOME ~ PRIVATE POOL/HOT TUB ~ PERFECT HAMPTONS GETAWAY ~ MBH

9.6 out of 10, Exceptional, (34)
"Our family enjoyed our stay at this spacious, clean comfortable house. Fully equipped kitchen, outdoor pool & hot tub. Great area for walking the neighborhood and down to the beach. Short drive to town of East Hampton."
STUNNING LUXURY HOME ~ PRIVATE POOL/HOT TUB ~ PERFECT HAMPTONS GETAWAY ~ MBH
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.
Don't see what you're looking for?
See all available properties in Village of Southampton
Save an average of 15% on thousands of hotels when you're signed in

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, (513)
"Nice place"
The price is AU$385
includes taxes & fees
21 Feb - 22 Feb
Southampton Inn

Harpoon House

3.0 star property
8.2 out of 10, Very good, (110)
"Delightful stay in the middle of Southampton Village. Close to all, extremely comfortable bed and well appointed junior suite with fine amenities. "
The price is AU$198
includes taxes & fees
23 Feb - 24 Feb
Harpoon House

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

10.0 out of 10, Exceptional, (98)
"Pam was very communicative prior to our stay and a welcoming host. The house was clean, centrally located, and spacious. "
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
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 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.

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

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr: This holiday home rental outside Village of Southampton offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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

With 129 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.