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Check prices for these dates

Next weekend
11 July - 13 July
In two weeks
18 July - 20 July
In one month
1 Aug - 3 Aug
In two months
29 Aug - 31 Aug

Featured Cottages in Amagansett

Fairy Tale Guest Cottage in Magic Garden by Pool
Property grounds

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (67)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool
Lovely Cottage in the Heart of Long Island Wine country
Beach

Lovely Cottage in the Heart of Long Island Wine country

9.8 out of 10, Exceptional, (25)
"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
Cozy cottage on Fort Pond Lake.
Exterior

Cozy cottage on Fort Pond Lake.

10.0 out of 10, Exceptional, (14)
"The lake house was a perfect retreat, perfectly located to town, train, trails and beach. We can’t wait to visit again !"
Cozy cottage on Fort Pond Lake.
Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday
Beach nearby, sun-loungers

Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday

9.6 out of 10, Exceptional, (44)
"A lovely beach cottage with bay views and easy walking access to the Atlantic beaches.The place was cozy and clean with expansive open views across reserve land to the bay.A bit tricky to find off the highway at night but we eventually got our bearings!"
Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday
Location and views! Located directly on Shinnecock Bay!
Smart TV

Location and views! Located directly on Shinnecock Bay!

9.0 out of 10, Wonderful, (26)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
The price is AU$1,114
includes taxes & fees
2 July - 3 July
Location and views! Located directly on Shinnecock Bay!
Luxurious 3 BR Cottage w/ Ocean View Balcony
A heated pool

Luxurious 3 BR Cottage w/ Ocean View Balcony

Luxurious 3 BR Cottage w/ Ocean View Balcony
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
On the beach

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

9.8 out of 10, Exceptional, (92)
"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 .
Sabbatical a Private guest cottage in Sag Harbor
Exterior

Sabbatical a Private guest cottage in Sag Harbor

9.6 out of 10, Exceptional, (9)
"I can’t thank enough our hostess Susan for her amazing hospitality and kindness! I strongly recommend her place to stay for vacation!"
Sabbatical a Private guest cottage in Sag Harbor
Ritz - East Hampton Cottage On The Water
Smart TV

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
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
TV, fireplace, video games, DVD player

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
Southampton cozy cottage by the beach
Beach

Southampton cozy cottage by the beach

The price is AU$1,462
includes taxes & fees
27 July - 28 July
Southampton cozy cottage by the beach
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Beach nearby, sun-loungers, beach towels

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

10.0 out of 10, Exceptional, (27)
"This is great property - perfectly renovated and close to everything including a nice North Fork beach in walking distance. Our host Bill communicates well and has thought of everything - house is well appointed and tastefully renovated with AirCon and washer/dryer. Sheets and Towels are clean and high quality! A beautiful, lush and grassy yard awaits your kids and the fire pit is perfect. Bill, our host was very nice in providing suggestions on where to go and what to do - some very nice...
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Hidden gem! Southampton beach cottage
Smart TV

Hidden gem! Southampton beach cottage

The price is AU$1,100
includes taxes & fees
14 July - 15 July
Hidden gem! Southampton beach cottage
Orient Village — Historic Bayfront Cottage — 2025 Season
Exterior

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
East Hampton/Springs Cottage- minutes walk to sea
Property grounds

East Hampton/Springs Cottage- minutes walk to sea

10.0 out of 10, Exceptional, (4)
"The cottage was exactly as described. Clean, well equipped and right by the beach. This place has everything you need. AC, cable tv, wifi and a fabulous location. While this is someone's well loved and maintained home, it is ready for guests with clean linens, comfy beds and a stocked kitchen. The outdoor space is great too. Great communication with the hosts. Close to beach, market and restaurants."
East Hampton/Springs Cottage- minutes walk to sea
Fabulous Waterfront Property in the Heart of Wine Country
Sun-loungers, beach towels

Fabulous Waterfront Property in the Heart of Wine Country

10.0 out of 10, Exceptional, (175)
"Beautiful and cozy lakeside retreat. Super serene and peaceful place to stay."
Fabulous Waterfront Property in the Heart of Wine Country
Kayak, Swim, Nature, Water. Privacy. One of best sites in Hamptons.
Exterior

Kayak, Swim, Nature, Water. Privacy. One of best sites in Hamptons.

10.0 out of 10, Exceptional, (29)
"We had a beautiful, quiet stay in this little cottage on the water. Gorgeous views, nice hikes nearby, and comfortable accommodations. Richard was a helpful and responsive host. "
Kayak, Swim, Nature, Water. Privacy. One of best sites in Hamptons.
Town walking distance-Bridgehampton Cottage
Beach nearby

Town walking distance-Bridgehampton Cottage

9.4 out of 10, Exceptional, (10)
"Walking distance to Bridgehampton and a short drive to sag harbor. Great for 2 couples."
Town walking distance-Bridgehampton Cottage
Walk to Beach: Long Island Wine Country Home!
Interior

Walk to Beach: Long Island Wine Country Home!

3.0 star property
Walk to Beach: Long Island Wine Country Home!
Southold Cottage w/ Patio & Grill - Walk to Beach!
Beach nearby

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

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