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Compare 135 Cottages in Village of Southampton with updated reviews, rates, and availability.

Orient Village — Historic Bayfront Cottage — 2025 Season

10.0 out of 10, Exceptional, (20)
"We had an amazing time enjoying the house and exploring the area. Fishing wasn’t fantastic, but that’s nobody’s fault. Would definitely go back!"
Orient Village — Historic Bayfront Cottage — 2025 Season

Hampton Cottage.

10.0 out of 10, Exceptional, (4)
"charming small cottage, very fresh, crisp, and comfortable! 100% redone, everything is brand new! we might have been the first guest. good location for Hamptons travel & shopping & beaches fun restaurants & music nearby, Cowfish, Roomba, Canal Cafe, Francesco Pizza-Gelato. Mrs and I had a wonderful time, cheers!"
Hampton Cottage.

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (91)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

Location and views! Located directly on Shinnecock Bay!

9.2 out of 10, Wonderful, (23)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
Location and views! Located directly on Shinnecock Bay!

Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

9.4 out of 10, Exceptional, (36)
"Lovely cottage beautifully decorated, close to restaurants, farm stands, and food stores. A least a 15 to 20 minute walk to the beach."
The price is SAR 521
SAR 1,410 total
includes taxes & fees
6 May - 7 May
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

10.0 out of 10, Exceptional, (25)
"The property was clean, exactly as advertised and extremely cozy and convenient. The host was super helpful and quick to respond!"
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Hamptons Vacation Rental w/ Seasonal Pool!

10.0 out of 10, Exceptional, (5)
"We really enjoyed the place. Very nice, very clean. Had a million things that people never think of while staying away at a random place for a vacation house."
Hamptons Vacation Rental w/ Seasonal Pool!

Charming 3-bedroom cottage in fabulous Greenport

Charming 3-bedroom cottage in fabulous Greenport

Southold Cottage w/ Patio & Grill - Walk to Beach!

Southold Cottage w/ Patio & Grill - Walk to Beach!

Cozy Cottage Ponquogue Hampton Bays

2.0 star property
Cozy Cottage Ponquogue Hampton Bays

Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays

2.0 star property
10.0 out of 10, Exceptional, (2)
"Excellent Host, great stay, beautiful property and set up and very modern."
Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays

Ritz - East Hampton Cottage On The Water

10.0 out of 10, Exceptional, (6)
"We enjoyed our time in the Ritz. It’s a great cottage surrounded by waterfront activities. The host was accommodating and welcoming."
Ritz - East Hampton Cottage On The Water

East End cottage on water!Pet Friendly! Wood FP Minutes from Hamptons & wineries

10.0 out of 10, Exceptional, (86)
"Property was a great home base for a weekend getaway. Location and accommodations were great."
The price is SAR 1,125
SAR 2,267 total
includes taxes & fees
6 May - 7 May
East End cottage on water!Pet Friendly! Wood FP Minutes from Hamptons & wineries

Walk to Love Lane! Immaculately renovated private cottage.

10.0 out of 10, Exceptional, (16)
"My wife and I stayed for the weekend for our Anniversary and this was the perfect location. Quaint and quite hideout with tons to do nearby."
Walk to Love Lane! Immaculately renovated private cottage.

Walk to Breakwater Beach in Heart of Wine Country

9.8 out of 10, Exceptional, (11)
"My wife and I traveled with our son and dog to Mattituck and had a great stay at this home. It was very comfortable and clean, and the host was easy to communicate with. I highly recommend staying here."
Walk to Breakwater Beach in Heart of Wine Country

Lovely Cottage in the Heart of Long Island Wine country

9.8 out of 10, Exceptional, (24)
"We love coming here-Eileen makes it so easy and we can’t get enough of the overall coziness and warmth of the place. Perfect for a quiet getaway!"
Lovely Cottage in the Heart of Long Island Wine country

East Hampton/Springs Cottage- minutes walk to sea

10.0 out of 10, Exceptional, (4)
"We really enjoyed this quaint cottage that really felt lovely me home. Very clean and well equipped Had a great time"
East Hampton/Springs Cottage- minutes walk to sea

Luxurious 3 BR Cottage w/ Ocean View Balcony

The price is SAR 2,246
SAR 4,034 total
includes taxes & fees
8 May - 9 May
Luxurious 3 BR Cottage w/ Ocean View Balcony

Fabulous Waterfront Property in the Heart of Wine Country

10.0 out of 10, Exceptional, (172)
"Beautiful and cozy lakeside retreat. Super serene and peaceful place to stay."
Fabulous Waterfront Property in the Heart of Wine Country

Lovely North Fork Beach Cottage (2 BR/2 bath)!

10.0 out of 10, Exceptional, (114)
"This cottage was so cute and cozy but very spacious! Can’t wait to come back here!"
Lovely North Fork Beach Cottage (2 BR/2 bath)!
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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Other property types in Village of Southampton

Minutes from the beach, brand new 4 bedroom

The price is SAR 3,000
SAR 5,874 total
includes taxes & fees
6 May - 7 May
Minutes from the beach, brand new 4 bedroom

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (283)
"Love the ocean view from the balcony"
The price is SAR 576
SAR 740 total
includes taxes & fees
6 May - 7 May
Windward Shores Ocean Resort

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (211)
"Very beautiful location and the room unforgettable ocean view will definitely come back"
The price is SAR 652
SAR 907 total
includes taxes & fees
7 May - 8 May
Cliffside Resort Condominiums
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.