Southampton Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Southampton holiday rentals

Outdoor dining

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
9.2 out of 10, Wonderful, (5 reviews)
"Very nice place and super responsive host. "
United States
Angelo D.
The price is HK$2,743
HK$4,602 total
includes taxes & fees
22 Jun - 23 Jun
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Beach nearby, sun-loungers, beach towels

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
Southampton
10.0 out of 10, Exceptional, (2 reviews)
"Had a great stay for a long weekend in the Hamptons. House was cozy and comfortable and in a good location."
United States
Beverly J.
The price is HK$5,149
HK$9,787 total
includes taxes & fees
23 Jun - 24 Jun
Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
Living area

Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
10.0 out of 10, Exceptional, (1 review)
"Great location. Loved the yard but for small pets the fence has some areas they could get under but overall it worked out. Just kept an eye on them.House very clean, comfortable. Host communication was excellent and would highly recommend for a visit to Southampton. Easy walk into town."
United States
Kathy B.
The price is HK$4,937
HK$10,539 total
includes taxes & fees
22 Jun - 23 Jun
Minutes from the beach, brand new 3 bedroom
Interior

Newly Renovated Pristine Southampton Colonial

Newly Renovated Pristine Southampton Colonial
Southampton
9.8 out of 10, Exceptional, (12 reviews)
"Great property, worked perfectly for my crew that was in town for an event. Great communication with Brian the owner and very easy stay. Would stay again!"
United States
Brian M.
The price is HK$15,160
HK$22,093 total
includes taxes & fees
28 Jun - 29 Jun
Newly Renovated Pristine Southampton Colonial
Property grounds

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, (15 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 HK$17,753
HK$24,333 total
includes taxes & fees
23 Jun - 24 Jun
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
1 bedroom, bed sheets

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY
East Hampton
8.6 out of 10, Excellent, (4 reviews)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
United States
Jennifer
The price is HK$1,516
HK$2,323 total
includes taxes & fees
22 Jun - 23 Jun
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
1 bedroom, bed sheets

Safari Tent Glamping,S6-CedarPt, East Hampton, NY

Safari Tent Glamping,S6-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We loved the surroundings, the pizza restaurant with live music and ping pong, and the friendly, warm atmosphere and kind staff. We do wish the bathrooms and especially the showers were cleaner."
United States
Lorraine
The price is HK$1,516
HK$2,323 total
includes taxes & fees
22 Jun - 23 Jun
Safari Tent Glamping,S6-CedarPt, East Hampton, NY
1 bedroom, bed sheets

Safari Tent Glamping,S11-CedarPt, East Hampton, NY

Safari Tent Glamping,S11-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Our tent was spacious and the bed was very comfortable with an incredible view of the harbor. Dave and Lee were very gracious and helpful. We especially enjoyed the Camp Store and the delicious omelets. Plus - how quiet and peaceful it was!"
United States
Lee
The price is HK$1,684
HK$2,542 total
includes taxes & fees
24 Jun - 25 Jun
Safari Tent Glamping,S11-CedarPt, East Hampton, NY
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (24 reviews)
"Great stay & great staff!"
United States
James
The price is HK$2,991
HK$3,417 total
includes taxes & fees
28 Jun - 29 Jun
North Fork Resort
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (258 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is HK$2,593
HK$3,303 total
includes taxes & fees
28 Jun - 29 Jun
Cliffside Resort Condominiums
Beach nearby

Seabreeze 4 Charming Cottage footsteps to beach

Seabreeze 4 Charming Cottage footsteps to beach
Hampton Bays
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is HK$870
HK$3,876 total
includes taxes & fees
28 Jun - 29 Jun
Seabreeze 4 Charming Cottage footsteps to beach
1 bedroom, bed sheets

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is HK$1,684
HK$2,542 total
includes taxes & fees
23 Jun - 24 Jun
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Shower, hair dryer, towels, shampoo

Villa Luz Family Home w/ heated pool & jacuzzi

Villa Luz Family Home w/ heated pool & jacuzzi
Hampon Bays
9.6 out of 10, Exceptional, (24 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is HK$878
HK$13,056 total
includes taxes & fees
22 Jun - 23 Jun
Villa Luz Family Home w/ heated pool & jacuzzi
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (316 reviews)
"Nice homey room"
United States
Andrew
The price is HK$3,356
HK$4,047 total
includes taxes & fees
8 Jul - 9 Jul
Windward Shores Ocean Resort
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is HK$1,795
HK$2,695 total
includes taxes & fees
23 Jun - 24 Jun
American Beech in Greenport - Petite King Room 7
Individually decorated, individually furnished, free WiFi, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (241 reviews)
"Very close to beach"
United States
Rabia
The price is HK$2,362
HK$2,954 total
includes taxes & fees
22 Jun - 23 Jun
Driftwood Resort
Dining

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is HK$1,708
HK$8,682 total
includes taxes & fees
29 Jun - 30 Jun
BlackBerry Private home with jacuzzi yearlong
Terrace/patio

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (17 reviews)
"Amazing views, beautiful property and pet friendly! Clean, well equipped."
United States
Ana B.
The price is HK$3,354
HK$12,299 total
includes taxes & fees
29 Jun - 30 Jun
Black Swan Beachfront Home with Jacuzzi year round
Exterior

Unit 1411: 1-Bedroom | 1st Floor-Garden View | Swordfish

Unit 1411: 1-Bedroom | 1st Floor-Garden View | Swordfish
Napeague
9.0 out of 10, Wonderful, (2 reviews)
"Fantastic as always!!"
United States
robert R.
Unit 1411: 1-Bedroom | 1st Floor-Garden View | Swordfish
Exterior

Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
The price is HK$2,312
HK$4,808 total
includes taxes & fees
22 Jun - 23 Jun
Lovely studio with AC in charming Sag Harbor
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 Southampton Hotel Reviews

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Ok stay, thank you."
Kevin 1-night trip
Posted 6 hours ago
The Bentley Hotel Southampton

Find out more about Southampton

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

  • View our selection of featured holiday rentals in Southampton
  • Use the map to find apartments and other holiday homes in the Southampton neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southampton while they last

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

Frequently asked questions

Can I find holiday rentals in Southampton?

Yes, there are holiday rentals in Southampton close to Southampton Cultural Center, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Southampton. Make sure you have time to check out the museums and festivals during your trip.

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

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.: This highly rated holiday home rental in Southampton offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a dishwasher and a stovetop can make your holiday run smoothly. Some other top choices in Southampton are Private 2.1 acre gated home with heated pool and tennis & pickleball court and Southampton 4BR Home | Pool, Game Room, 1.4 mi to Shinnecock.

How many holiday rentals are there in Southampton?

Expedia has 547 holiday rentals for your stay in Southampton.

What can I see and do in Southampton?

Enjoy the outdoors at The Hamptons Beaches and Cooper's Beach, or simply take in cultural attractions like Shinnecock Nation Cultural Center and Museum and Southampton Historical Museum. Other places in town to visit include Southampton Cultural Center and North Main Street Historic District.

What are holiday rentals like in Southampton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Southampton. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a family trip.