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Compare 225 Cottages in Shelter Island with updated reviews, rates, and availability.

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

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

Charming 3-bedroom cottage short walk to Chalker Beach

Charming 3-bedroom cottage short walk to Chalker Beach

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (25)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is SAR 450
SAR 722 total
includes taxes & fees
11 May - 12 May
1-bedroom cottage with Grove Beach 🏖️ access.

The gardners Cottage 1 mile from long Island Sound - pet friendly

10.0 out of 10, Exceptional, (13)
"Property is charming, beautifully decorated, clean. Host was very responsiveand even shared produce from her lovely garden! We hope to return."
The gardners Cottage 1 mile from long Island Sound - pet friendly

Enchanted Waterfront Cottage

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

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!

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

Charming Old Lyme Cottage, Steps to Private Beach!

8.6 out of 10, Excellent, (7)
"The location and property were perfect for our stay. Homeowner was very accommodating. Can’t wait to go back!!!!"
Charming Old Lyme Cottage, Steps to Private Beach!

Charming Westbrook Cottage, Steps to Private Beach

10.0 out of 10, Exceptional, (3)
"Cozy cottage, good location, nice access to the Sound."
Charming Westbrook Cottage, Steps to Private Beach

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (70)
"Perfect and cozy home base for visiting with family!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park

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

10.0 out of 10, Exceptional, (14)
" Very clean, plenty of room for multi generational family and the beach was very relaxing. Will stay again."
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

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

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (71)
"Perfect stay in Madison. Beautiful location. Clean and comfy house. Will be back!"
Direct waterfront renovated cottage.

'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

Beach Cottage

10.0 out of 10, Exceptional, (3)
"The cottage was very comfortable and had everything that I needed. The hosts were very attentive. The location was perfect; a quiet area just one block from a private beach. I would definitely stay again."
The price is SAR 679
SAR 1,545 total
includes taxes & fees
5 May - 6 May
Beach Cottage

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
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, (1171)
"excellent overall stay"
The price is SAR 567
SAR 721 total
includes taxes & fees
19 May - 20 May
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (374)
"Good for a short stay "
The price is SAR 595
SAR 721 total
includes taxes & fees
5 May - 6 May
Montauk Oceanside Suites

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (251)
"On the beach Heated pool Great facilities"
The price is SAR 759
SAR 1,072 total
includes taxes & fees
19 May - 20 May
The Surf Club
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.