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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 227 Cottages in Shelter Island with updated reviews, rates, and availability.

Fairy Tale Guest Cottage in Magic Garden by Pool
Outdoor pool

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (66)
"Enjoyed our stay very much. Place is beautiful, clean, hosts cannot b nicer. Definitely hope to return "
Fairy Tale Guest Cottage in Magic Garden by Pool
Charming Westbrook Cottage, Steps to Private Beach
Microwave, coffee/tea maker, toaster, cookware/dishes/utensils

Charming Westbrook Cottage, Steps to Private Beach

9.6 out of 10, Exceptional, (4)
"Had a great stay!"
Charming Westbrook Cottage, Steps to Private Beach
Sweet Cottage in Beach Community
Beach nearby, sun loungers, beach towels

Sweet Cottage in Beach Community

10.0 out of 10, Exceptional, (6)
"Cute cottage, newly refurbished, quiet, nice neighborhood, well stocked."
Sweet Cottage in Beach Community
Charming 2-bedroom cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Outdoor dining

Charming 2-bedroom cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

2.0 star property
10.0 out of 10, Exceptional, (1)
"My friends and I had a great weekend here. The property is accurately described as listed. It was just enough space for a weekend. There were 3 of us. We used the fold down couch as the 3rd bed which was a good bed. Communication with the host was excellent. The property inside and out was great. We sat outside in the backyard for a while. The walk over the bridge to the Niantic boardwalk wasn’t too long when the weather is good. And we sat outside at Fat Tuna which was within walking distance...
The price is AED 613
AED 1,267 total
includes taxes & fees
2 Jun - 3 Jun
Charming 2-bedroom cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Location and views! Located directly on Shinnecock Bay!
Smart TV

Location and views! Located directly on Shinnecock Bay!

9.0 out of 10, Wonderful, (24)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
Location and views! Located directly on Shinnecock Bay!
Beach Cottage
Fridge, microwave, oven, stovetop

Beach Cottage

10.0 out of 10, Exceptional, (4)
"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 AED 735
AED 1,612 total
includes taxes & fees
4 Jun - 5 Jun
Beach Cottage
Enchanted Waterfront Cottage
Smart TV, fireplace, books

Enchanted Waterfront Cottage

9.0 out of 10, Wonderful, (19)
"The location was perfect. Very comfortable."
Enchanted Waterfront Cottage
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
On the beach, sun loungers, beach towels

4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

9.8 out of 10, Exceptional, (70)
"Very enjoyable- we've booked already for next summer!"
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
The gardners Cottage 1 mile from long Island Sound - pet friendly
Property grounds

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
Direct waterfront renovated cottage.
TV, books

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.
Cozy cottage on Fort Pond Lake.
Miscellaneous

Cozy cottage on Fort Pond Lake.

10.0 out of 10, Exceptional, (12)
"Great location! We loved our stay at the cottage and can’t wait to return. Danny was so easy to communicate with and he really went the extra mile to make sure we enjoyed our stay. "
Cozy cottage on Fort Pond Lake.
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Exterior

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (71)
"Perfect and cozy home base for visiting with family!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more
Miscellaneous

Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more

10.0 out of 10, Exceptional, (2)
"Wonderful stay in a remodeled stone house. Host was great and the house is very comfortable. We really enjoyed the beautifully restored building and all the touches throughout. "
The price is AED 1,157
AED 1,959 total
includes taxes & fees
2 Jun - 3 Jun
Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more
Charming Old Lyme Cottage, Steps to Private Beach!
Coffee/tea maker

Charming Old Lyme Cottage, Steps to Private Beach!

7.8 out of 10, Good, (8)
"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!
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, (26)
"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
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
Inviting 3BR Beachfront Cottage in Hawk's Nest – Summer Escape Awaits!
Beach

Inviting 3BR Beachfront Cottage in Hawk's Nest – Summer Escape Awaits!

Inviting 3BR Beachfront Cottage in Hawk's Nest – Summer Escape Awaits!
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Fridge, microwave, oven, stovetop

A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

10.0 out of 10, Exceptional, (2)
"This was an amazing place to stay. Beautiful property and EXCELLENT hosts! Thank you!"
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
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, (173)
"Beautiful and cozy lakeside retreat. Super serene and peaceful place to stay."
Fabulous Waterfront Property in the Heart of Wine Country
Direct LI sound waterfront cottage, one level living in Hawks Nest Beach
Sun loungers

Direct LI sound waterfront cottage, one level living in Hawks Nest Beach

Direct LI sound waterfront cottage, one level living in Hawks Nest 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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