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Compare 224 Cottages in Shelter Island with updated reviews, rates, and availability.

Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

10.0 out of 10, Exceptional, (14)
"This rental is so unique with the 2 sides, and was absolutely perfect for our wedding weekend. We had the groom’s friends staying on one side, and my friends staying on the other side. The two sides are connected through the sunroom and the backyard space is great which made bringing the whole group together so easy. The setup was also perfect for me to get ready on my own separate side the day of the wedding so that my now husband wouldn’t see me. The decor and cleanliness of the house were...
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

9.2 out of 10, Wonderful, (23)
"Spent a weekend in this cottage while attending an event for my daughter. Very cozy and comfortable. Host was great, with excellent communication. Renovations are taking place in adjacent units, however it did not impact my stay. Highly recommend. "
The price is AED 327
AED 639 total
includes taxes & fees
31 Mar - 1 Apr
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

Charming Westbrook Cottage, Steps to Private Beach

10.0 out of 10, Exceptional, (2)
"Cozy cottage, good location, nice access to the Sound."
Charming Westbrook Cottage, Steps to Private Beach

Charming Old Lyme Cottage, Steps to Private Beach!

8.6 out of 10, Excellent, (7)
"We booked last minute as we decided to join family staying in Old Lyme. This cottage was just perfect for our needs. My husband and I along with our 19 year old stayed here. Clean, newly remodeled and amenities to meet our needs for a 3 day beach retreat. Simple, but practical. Close to beach and a/c was a treat during the heat wave! ⭐️⭐️⭐️⭐️⭐️"
Charming Old Lyme Cottage, Steps to Private Beach!

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!

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (107)
"Cute place, very clean"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

Enchanted Waterfront Cottage

9.0 out of 10, Wonderful, (19)
"The location was perfect. Very comfortable."
Enchanted Waterfront Cottage

Classic Cottage in Best Private Community in Old Lyme CT.

10.0 out of 10, Exceptional, (27)
"Great little house very close to the sound. Met our needs perfectly!"
Classic Cottage in Best Private Community in Old Lyme CT.

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 AED 4
AED 1,101 total
includes taxes & fees
10 Apr - 11 Apr
Orient Village — Historic Bayfront Cottage — 2025 Season

'Grandma's Cottage' w/ Sunroom: Walk to Beach

8.0 out of 10, Very Good, (3)
"Terrific location. 1 block from the beach."
'Grandma's Cottage' w/ Sunroom: Walk to Beach

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

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC

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!

Beach Cottage

10.0 out of 10, Exceptional, (3)
"Excellent experience. Great host. Clean, inviting property near beach. Cozy home. Good value. Will stay again. Thank you. "
The price is AED 1,098
AED 2,052 total
includes taxes & fees
25 Mar - 26 Mar
Beach Cottage

Charming 3-bedroom cottage short walk to Chalker Beach

Charming 3-bedroom cottage short walk to Chalker Beach

Direct waterfront 3-bedroom cottage in Old Lyme, Hawks Nest Beach

Direct waterfront 3-bedroom cottage in Old Lyme, Hawks Nest Beach

Charming 3-bedroom cottage in fabulous Greenport

Charming 3-bedroom cottage in fabulous Greenport

Charming Old Saybrook Cottage < 1 Mi to Beach

10.0 out of 10, Exceptional, (27)
"Was close to the beach and town. "
Charming Old Saybrook Cottage < 1 Mi 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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Other property types in Shelter Island

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1144)
"Great place! "
The price is AED 481
AED 621 total
includes taxes & fees
25 Mar - 26 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 AED 500
AED 611 total
includes taxes & fees
27 Mar - 28 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 AED 484
AED 633 total
includes taxes & fees
25 Mar - 26 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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