Southampton Holiday Rentals: Short-Term Accommodations for Rent

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Holiday Rentals in Southampton

Juliana H.

HK$4,536 total

includes taxes & fees

3 Nov - 4 Nov

Okito H.

HK$8,620 total

includes taxes & fees

4 Nov - 5 Nov

Richard A. F.

HK$13,950 total

includes taxes & fees

1 Dec - 2 Dec

HK$1,731 total

includes taxes & fees

3 Nov - 4 Nov

HK$3,533 total

includes taxes & fees

9 Nov - 10 Nov

John W.

HK$2,937 total

includes taxes & fees

4 Nov - 5 Nov

STEPHANIE C.

HK$6,845 total

includes taxes & fees

6 Nov - 7 Nov

Elaine P.

HK$10,387 total

includes taxes & fees

3 Nov - 4 Nov

dean

HK$2,325 total

includes taxes & fees

3 Nov - 4 Nov

Lisa w.

HK$9,881 total

includes taxes & fees

9 Nov - 10 Nov

"Our family / extended family was in town for over a week for the Hampton Classic horse show. We all enjoyed or stay at this wonderful home: beautiful newly renovated open space, outstanding kitchens (indoors and outdoors), numerous areas to have separate down time, excellent in suite bedroom / bathrooms including three bedrooms suites with king beds, fabulous backyard with a private pool, and exceptionally clean with all amenities needed. The owners were also incredible; extremely responsive,...

Kristin C.

HK$42,585 total

includes taxes & fees

3 Nov - 4 Nov

HK$7,793 total

includes taxes & fees

4 Nov - 5 Nov

HK$18,773 total

includes taxes & fees

23 Nov - 24 Nov

Smart TV, fireplace, video games, stereo

Ruth E.

HK$6,090 total

includes taxes & fees

1 Dec - 2 Dec

Jeannette M.

HK$4,314 total

includes taxes & fees

5 Nov - 6 Nov

Parent From The Heart, Inc. E.

HK$2,175 total

includes taxes & fees

10 Nov - 11 Nov

HK$50,087 total

includes taxes & fees

7 Nov - 8 Nov

"Step away from your busy schedule, step back in time, and step down to the beach. Bayside Cottage is an idyllic, charming, and rare place -- one increasingly harder to find as grandiose properties populate many parts of the Island. Thankfully the North Fork has retained much of its character since we began visiting some 20 years ago, and Orient is beautifully preserved with a lot of tender loving care, especially towards nature. It was turtle season in June! At Bayside, circa 1887, one doesn't...

Jennifer G.

HK$5,513 total

includes taxes & fees

30 Nov - 1 Dec

Anonymous traveller

HK$9,126 total

includes taxes & fees

3 Nov - 4 Nov

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Top Southampton Hotel Reviews

The Bentley Hotel Southampton

10/10 Excellent

"The staff was beyond helpful and nice, the rooms are huge and clean. Would definitely recommend "

Harpoon House

10/10 Excellent

"We were looking for a quick overnight in the East End, and the Harpoon House exceeded our expectations in every way. The room was spacious (a suite!) and well-appointed, blending the charm of the original 1648 (!) building with modern amenities and furnishings. We didn't take advantage of the on-property restaurant (formerly Blu Mar), but the menu - by acclaimed chef Rocco DiSpirito - looked excellent, if a bit pricey. Location was ideal, within easy walking distance of all Main Street shops and restaurants, and less than a mile to the beach. And, although things were a bit quieter than in the height of summer - not a bad thing! - we loved being out there for the fall harvest season, with wineries and farms in full swing. All-in-all, our stay at the Harpoon House made for a perfect fall weekend in the Hamptons - highly recommended. "

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

10/10 Excellent

"The host company was very responsive and the house was in a good location - close to down town and not far from the beach. The bedrooms and bathrooms were very nice. The kitchen was nice, as well, but a bit small for the property. Everything inside the house was clean and tidy."

Hamlet Inn

10/10 Excellent

"This was the perfect place to stay right down the street from Stony Brook University. We like that this hotel was small and we parked right outside of our room. Everything was clean and neatly organized. Plenty of towels and toiletries. It was the perfect hotel for one night so that I didn't have to drive to my conference at SBU in the morning. It would be a nice place for a weekend as well. The staff was very pleasant and welcoming. "

Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

10/10 Excellent

"We are from out of town and had a wedding to attend in Bridgehampton. We decided to rent this cute home because of it's location (which was excellent) and we liked the fact that each of the three bedrooms had it's own bathroom. Two of the bedrooms are quite large and comfortable. The third bedroom is considerably smaller but had a queen bed and still fit our needs.A short 8 minute walk puts you right into the town of Southhampton with great shopping and restaurants. Both days we walked to the beach to get exercise. It's a little over 1.5 miles each way. Our host, Pam was very accommodating and responsive. We loved how there were many thoughtful details throughout the house to make her guests feel comfortable. She had a stocked coffee bar area, extra toiletries, hair dryers, multiple irons, equipment for games and activities etc. I would definitely recommend staying here."

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

10/10 Excellent

"The perfect house for a family-and-friends getaway! The host was extremely accommodating and quick to respond to any questions. The home is very comfortable and well-suited for larger groups, especially families with small children. We loved our daily walks to the beach and exploring the nearby towns. Highly recommend this property and we look forward to returning! "

Find out more about Southampton

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Frequently asked questions

Can I find holiday rentals in Southampton?

Yes, there are holiday rentals close to the most popular sights in Southampton, 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?

Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...: 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. It has 6 bedrooms, as well as a kitchen with a stovetop, a microwave and a coffee maker, so that you can cook with friends or family. Some other top choices in Southampton are Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping and Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families.

How many holiday rentals are there in Southampton?

Expedia has 482 holiday rentals for your stay in Southampton.

What can I see and do in Southampton?

Enjoy the outdoors at Cooper's Beach and The Hamptons Beaches, 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 Arts Center and Southampton Cultural Center.

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.

Southampton Holiday Rentals

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Check prices for these dates

Holiday Rentals in Southampton

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Minutes from the beach, brand new 4 bedroom

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

North Fork Cottages & RV Resort

Hidden gem! Southampton beach cottage

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Cozy quiet gem, private & fenced in backyard

Private beach on a fenced in property sunset views

Cliffside Resort Condominiums

Year-Round Private Jacuzzi / Peaceful Fenced Yard

BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town

Stylish Woody Interior 1BR+Loft w/ Beach Access

Canoe Place Waterfront Residences

East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

American Beech in Greenport - Petite King Room 7

Spacious 5-bedroom house with water views and 2 houses from the bay.

Orient Village — Historic Bayfront Cottage — 2025 Season

Beautifully farmhouse

Top Southampton Hotel Reviews

The Bentley Hotel Southampton

The Atlantic Hotel

Harpoon House

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

Hamlet Inn

Minutes from the beach, brand new 4 bedroom

Southampton Inn

Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

Find out more about Southampton

Explore a world of travel with Expedia

Frequently asked questions

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