Holiday rentals in Southampton
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Top-rated holiday rentals in Southampton
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Guest suite in Hampton Bays
4.98 out of 5 average rating, 311 reviewsCHARMING 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.
20–27 Aug
Guest house in Hampton Bays
4.96 out of 5 average rating, 145 reviewsWELCOME 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.
17–24 Sep
Cottage in Southampton
4.93 out of 5 average rating, 60 reviewsModern Southampton Cottage | Heated Pool & Peloton
Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air. Newly renovated kitchen with high end appliances, large outdoor deck that is perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 mins to Coopers Beach.
14–21 Nov
Holiday rentals for every style
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Popular amenities for Southampton holiday rentals
Other great holiday rentals in Southampton
Home in Southampton
5.0 out of 5 average rating, 37 reviewsBay View Stunner, Modern 6 Bedroom w Heated Pool
16–23 May
Home in Southampton
5.0 out of 5 average rating, 17 reviewsPerfect Lake Cottage weekend Hamptons special
31 Oct – 7 Nov
Home in Southampton
5.0 out of 5 average rating, 20 reviewsTranquility at the Water’s Edge
29 Oct – 5 Nov
Flat in Southampton
4.85 out of 5 average rating, 27 reviewsSpacious One Bedroom Apartment, Close to Beaches
12–19 Nov
Guest house in Southampton
4.98 out of 5 average rating, 45 reviewsSouthampton Modern Barn, Private Hot Tub and Pool
19–26 Aug
Home in Sag Harbor
4.84 out of 5 average rating, 45 reviewsModern Home in Sag Harbor, NY
16–23 May
Cottage in Bridgehampton
5.0 out of 5 average rating, 49 reviewsBridgehampton Cottage Close to Town, South of HWY
15–22 Apr
Home in Southampton
4.97 out of 5 average rating, 35 reviewsBeautiful Southampton Village Home with Pool
12–19 May
Home in Southampton
4.95 out of 5 average rating, 44 reviewsSouthampton Village Newly Built Gem
23–30 Nov
Home in Southampton
5.0 out of 5 average rating, 55 reviewsDream home in SH with heated private Pool
27 Sep – 4 Oct
Cottage in Sag Harbor
5.0 out of 5 average rating, 27 reviewsLuxury Gem At The Heart of Sag Harbor Village
23–30 May
Holiday home in Southampton
5.0 out of 5 average rating, 39 reviews5BR, Luxury Home, Pool, Yard Close to Beach & Town
28 Oct – 4 Nov
Quick stats about holiday rentals in Southampton
Total rentals | 640 properties |
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Rentals with a pool | 340 properties have a pool |
Pet-friendly rentals | 260 properties allow pets |
Family-friendly rentals | 390 properties are a good fit for families |
Total number of reviews | 7.3T reviews |
Nightly prices starting at | ₹833 before taxes and fees |
Destinations to explore
- New City Holiday rentals
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