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Compare 118 Cottages in Wainscott with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (25)
"Before my trip even began, communication with Bill was exceptional. Bill was very responsive throughout my entire 3 day stay. The entire house was recently renovated, and I can tell not only did they invest a lot of money in the renovation, but they were very thoughtful in all the upgrades they made. The neighborhood is also very peaceful. Whether you make a left or right, you’re only a couple blocks from the beach. My wife and I really enjoyed staying at this house. It was perfect for us as a...
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

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

9.8 out of 10, Exceptional, (91)
"We stayed for the weekend and couldn't have had a better time! The home is clean and lovely with a well stocked kitchen, comfortable beds and an unbeatable views! Very close to wineries, downtown Greenport and the Shelter Island ferry. Patrick, the owner, had great tips on local activities and was an all around great guy. Thank you! We'll be back! Patrick"
'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!

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!"
The price is SAR 4
SAR 1,125 total
includes taxes & fees
10 Apr - 11 Apr
Orient Village — Historic Bayfront Cottage — 2025 Season

Lovely Cottage in the Heart of Long Island Wine country

9.8 out of 10, Exceptional, (24)
"we had such a fun weekend out in southold! Cottage was perfect for us for a cold rainy weekend. Everything was so close to the house. Will definitely be back in the summer!"
Lovely Cottage in the Heart of Long Island Wine country

Hamptons Vacation Rental w/ Seasonal Pool!

10.0 out of 10, Exceptional, (5)
"My family enjoyed staying at this lovely property. The backyard was especially great! My kids splashed in the heated pool and jumped on the trampoline every day! The location was ideal and very close to the beach. We would definitely return. "
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!

Town walking distance-Bridgehampton Cottage

9.4 out of 10, Exceptional, (10)
"Great last minute stay with our pup. House offered ability to have our dog and a back yard for him to play."
Town walking distance-Bridgehampton Cottage

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)
"this lovely cottage was very comfortable and accommodating to our group (4 adults) Clean,quiet,and equipped!! Backyard view was perfect to your serenity and 10 minute walk to the beautiful beach! Area is friendly, easy walking neighborhood, litter free, away from highways. The owner is very amicable and helpful with anything! We had other friends staying in other accommodations~ because we were all here for a wedding~ they all paid more and did not have all the benefits that we did! This place...
Ritz - East Hampton Cottage On The Water

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

8.6 out of 10, Excellent, (25)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

Walk to Love Lane! Immaculately renovated private cottage.

10.0 out of 10, Exceptional, (16)
"Prefect size for us, 2 adults, 2 small kids and the dog. House was clean and fully stocked with anything we could have needed. "
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

Hampton Cottage.

10.0 out of 10, Exceptional, (3)
"we had a great stay at this property. the house was perfect. great value for the price. it is new and modern and extremely clean. the area itself was also nice. on a dead end street so nice and secluded. the host also included many amenities for guests to use which was a plus. would definitely stay here again. "
The price is SAR 784
SAR 1,107 total
includes taxes & fees
25 Mar - 26 Mar
Hampton Cottage.

Cozy cottage on Fort Pond Lake.

10.0 out of 10, Exceptional, (12)
"Cottage met and exceeded our needs! Loved being right on the water. Danny was an excellent host!"
Cozy cottage on Fort Pond Lake.

East Hampton/Springs Cottage- minutes walk to sea

10.0 out of 10, Exceptional, (4)
"The home is very quaint and well appointed. There were many things that we could avail ourselves with. A kayak, a bike, beach chairs, greens in the garden, BBQ grill, a very nice pair of binoculars, a boogie board etc. Lots of interesting wall decorations of drawings and paintings. Close to the very nice towns of Montauk and Sag Harbor. The beach is nearby. For the ocean side we really enjoyed Hither Hills State Park."
East Hampton/Springs Cottage- minutes walk to sea

Luxurious 3 BR Cottage w/ Ocean View Balcony

The price is SAR 1,872
SAR 3,421 total
includes taxes & fees
1 Apr - 2 Apr
Luxurious 3 BR Cottage w/ Ocean View Balcony

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

10.0 out of 10, Exceptional, (113)
"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)!

HAMPTONS 32nd ANNUAL FILM FESTIVAL, OCTOBER 4TH-14TH PERFECT COTTAGE FOR HIFF

2.0 star property
HAMPTONS 32nd ANNUAL FILM FESTIVAL, OCTOBER 4TH-14TH PERFECT COTTAGE FOR HIFF
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 Wainscott

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1140)
"Great place. Love it in the off season for the quietness."
The price is SAR 491
SAR 634 total
includes taxes & fees
24 Mar - 25 Mar
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (366)
"Had a great stay here . Staff was friendly and check in and out was a breeze . Was very clean and comfortable. Only complaint was I couldn’t get a hot shower . Otherwise place is excellent. Shops , restaurants and bars are all a short walk . "
The price is SAR 510
SAR 624 total
includes taxes & fees
24 Mar - 25 Mar
Montauk Oceanside Suites

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (275)
"Beautiful location, clean property, and nice staff. Just hard to turn in to the parking lot but not much that the hotel can do for that. The private beach is stunning. "
The price is SAR 494
SAR 646 total
includes taxes & fees
26 Mar - 27 Mar
Windward Shores Ocean Resort
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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