Holiday rentals in Southampton

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Top-rated holiday rentals in Southampton

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Guest favourite

Guest suite in Hampton Bays

4.98 out of 5 average rating, 315 reviews

CHARMING OCEAN BUNGALOW

My ocean Bungalow is super well located in Hampton Bays. You will be 10 minutes away from the center of town where the Hampton Bays train station is. You also have Starbucks, Ride Aid, king Kullen, and great eateries at your fingertips. You will also have another two great supermarkets; Stop&Shop and Wild by Nature natural food store. You will be staying in a room with a feeling of a Junior Suite with approximately 400sq feet, a much larger area than a standard room. It has an attached small full bathroom, a living space that I call “home theater” with a 75” smart TV, a wet Bar with Coffee, Expresso and Tea, your own refrigerator. No heavy cooking is allowed indoors but I will offer a grill outside, for the most gastronomically inclined guests ... there’s no dining area but you are more welcome to use the dining table at the outdoor stone patio. One of the nicest thing about our location is that we are 5 minutes from Ponquogue Beach with excellent near by restaurants such as Oklands, Sundays on the Bay, on Beach Road and Dockers waterside on Dune Road. Meschutt beach is also a great location with live music throughout the summer, not a beach for surfers or adventure swimmers, since it’s on Peconic Bay, but on a plus side, there’s a full outdoor bar for adults, I love their Rum punch, and a full service snack bar, and a gift shop that sells beach gear... etc.

27 Oct – 3 Nov

$390 SGD per night

Guest favourite

Flat in Sag Harbor

4.96 out of 5 average rating, 132 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

28 Aug – 4 Sep

$518 SGD per night

Guest favourite

Guest house in Hampton Bays

4.96 out of 5 average rating, 146 reviews

WELCOME TO THE LOVE SHACK BY THE SEA

Escape the city, work in nature! Totally private cottage with garden views , central air and heated floors. 1 mile from pristine beaches and center of town, LIRR, Hampton Jitney, 3 large grocery stores, Starbucks, organic market, shopping & restaurants. King bed, cable TV, refrigerator w/ice, microwave, outdoor grill, private yard, Perfect for couples, solo, 1-2 small kids. We welcome small dogs for a $100 fee. Please message us with the size and type. Working couple/owners in main house.

4–11 May

$483 SGD per night

Guest favourite

Guest house in Southampton

4.95 out of 5 average rating, 411 reviews

Tiny Home in Prime Spot in Southampton Village

Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in an easily accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station and a 5 min. walk to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet!

23–30 Sep

$491 SGD per night

Guest favourite

Cottage in Southampton

4.96 out of 5 average rating, 100 reviews

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

6–13 Jan

$1,375 SGD per night

Guest favourite

Home in Southampton

5.0 out of 5 average rating, 34 reviews

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Chic, 5-bedroom, 3.5 half-bath home is close to the water and the village of Southampton. The sparkling pool has a beautiful backdrop of a lushly landscaped garden. Southern exposure in the backyard brings an abundance of sunshine inside and out. The home includes an outdoor sauna, fire pit and rock garden perched above the pool for your very own spa retreat. The inside of the home is thoughtfully designed with a relaxed, chic & luxury feel making it the perfect Hamptons getaway.

13–20 Feb

$999 SGD per night

Guest favourite

Home in Southampton

4.91 out of 5 average rating, 179 reviews

Peaceful Hamptons Cottage

Looking for a getaway? Nestled into one of the largest preserves in the Hamptons, this sunny newly renovated beachy cottage is the perfect retreat. The legendary Hamptons beaches, wineries, Southampton Village, and the world famous golf courses are less than a 10 minute drive away. There are many nearby essential shops, farm stands & restaurants. Set up for WFH with hi-speed wifi and a desk. Abuts a large nature preserve with hiking paths. Lots of deer will roam by your window!

14–21 Jul

$867 SGD per night

Guest favourite

Home in Southampton

4.9 out of 5 average rating, 215 reviews

PICTURE PERFECT SOUTHAMPTON HOME-

Picture Perfect 3 bedroom 1.5 Bath Cottage located in the heart of Southampton. The home is conveniently located close to Southampton, Bridgehampton and Sag Harbor towns. Additionally, there is close access to both Bay and Ocean Beaches. The Newly renovated home gives you a peaceful and serene feeling everyday. Dogs are accepted on a case by case basis. Cats are not permitted. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

14–21 Sep

$784 SGD per night

Guest favourite

Flat in Sag Harbor

4.98 out of 5 average rating, 117 reviews

Sag Harbor Retreat

Experience the many wonderful things the Hamptons has to offer in the Summer in centrally-located Sag Harbor. Our place is a professionally-decorated luxury apartment with its own entrance, yard and two parking spaces. This home-away-from-home is an immaculate and well-appointed retreat located in Sag Harbor. Great for couples and solo adventurers. Close to Sag Harbor's Main Street with abundant recreational activities, shopping and restaurants.

16–23 May

$1,083 SGD per night

Guest favourite

Home in Southampton

4.87 out of 5 average rating, 237 reviews

Secluded Southampton Luxury Estate with tennis 288

We are only listed on Airbnb no other sites Hot water is included . The estate is a short ride to all art and culture museums,parks, coopers beach, ocean beaches, fishing, downtown, village, night life, restaurants and shopping. One of the best locations to access north fork wineries and still be just minutes from the town of Southampton. Shampoo, soap and conditioner are not supplied so make sure to bring your own. Small

27 Oct – 3 Nov

$1,306 SGD per night

Guest favourite

Flat in Southampton

4.96 out of 5 average rating, 165 reviews

Sunny Southampton Studio

Newly renovated sun drenched, spacious studio in Southampton. Five minute drive to Main Street, while still in close proximity to some of the most beautiful beaches. Queen size bed and queen size pull out couch. Full kitchen with new appliances and full bathroom. BEACH PASS for Coopers beach is available upon advanced request—please let me know the day before you arrive

30 Jun – 7 Jul

$689 SGD per night

Guest favourite

Loft in Southampton

4.89 out of 5 average rating, 145 reviews

Getaway cottage privet and quiet

Cottage is on the property with the owner but it is completely separate from our own home. We are in a lovely quiet neighborhood. We are friendly with animals we have our own dog as well. 5 Minute drive to the bay and 10-minute drive to the ocean. Baby crib can be additionally installed. Pool is shared with my family on property

21–28 Nov

$538 SGD per night