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Our top choices for Shelter Island cottages
1. North Fork Resort
North Fork ResortGreenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
Altynai
The price is £264
includes taxes & fees
12 Nov - 13 Nov
2. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to TownGreenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
Jeannette M.
The price is £568
includes taxes & fees
10 Nov - 11 Nov
3. Steps to the beach | Seabreeze Cottage #3
Steps to the beach | Seabreeze Cottage #3Hampton Bays
6.0 out of 10, (3 reviews)
"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils.
The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off.
The last straw was the huge spider that jumped down from the closet onto me.
We ended up leaving after less than 24 hours and...
Lydia
The price is £348
includes taxes & fees
30 Nov - 1 Dec
4. 1-bedroom cottage with Grove Beach 🏖️ access.
1-bedroom cottage with Grove Beach 🏖️ access.Clinton
9.8 out of 10, Exceptional, (66 reviews)
"We enjoyed our stay"
JM B.
The price is £170
includes taxes & fees
10 Nov - 11 Nov
5. The gardners Cottage 1 mile from long Island Sound - pet friendly
The gardners Cottage 1 mile from long Island Sound - pet friendlyClinton
9.8 out of 10, Exceptional, (31 reviews)
"Very nice cozy cottage, the host was very friendly"
Wink V.
The price is £257
includes taxes & fees
5 Nov - 6 Nov
6. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!Madison
9.4 out of 10, Exceptional, (3 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
Samantha D.
The price is £261
includes taxes & fees
6 Nov - 7 Nov
7. Adorable Cottage with Cottage porch, walk to water & town
Adorable Cottage with Cottage porch, walk to water & townWestbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and comfortable"
Francine F.
The price is £423
includes taxes & fees
5 Nov - 6 Nov
8. Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & BoardwalkWaterford
10.0 out of 10, Exceptional, (36 reviews)
"The stay was great and the host was more than kind and very helpful! "
Jenna K.
The price is £238
includes taxes & fees
10 Nov - 11 Nov
9. Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Getaway-Near Beaches, Train & ShorelineWestbrook Center
The price is £273
includes taxes & fees
17 Nov - 18 Nov
10. Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage
Hamptons Oceanfront Oasis - Cozy 1-bedroom cottageHampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is £299
includes taxes & fees
12 Nov - 13 Nov
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.
Learn more about Shelter Island
Nestled between Long Island's forks, this serene island offers pristine beaches and kayaking through Mashomack Preserve's coastal wetlands. Rent bikes to explore historic mansions and stop at Sunset Beach for seafood with spectacular evening views across Shelter Bay.
