Shelter Island Cottages

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Our top choices for Shelter Island cottages

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton

Philip L.

includes taxes & fees

11 Jun - 12 Jun

North Fork Resort

Greenport

James

includes taxes & fees

15 Jun - 16 Jun

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Waterford

Dianne B.

includes taxes & fees

10 Jun - 11 Jun

Beach Cottage, private beach and pass

East Lyme

Kerri G.

includes taxes & fees

23 Jun - 24 Jun

NEW Coastal Cottage 2 Miles to Beach + Lake Access

Clinton

"We had a wonderful stay at this cottage. It was comfortable, beautifully decorated, and exceptionally clean. Even though the weather during our trip was terrible, we still thoroughly enjoyed our time there.The hosts were very helpful and provided all the information we needed about the cottage as well as local attractions and activities. Overall, it was an excellent experience, and I would absolutely give it 5 stars."

Erin M.

includes taxes & fees

10 Jun - 11 Jun

Seabreeze 4 Charming Cottage walk to US Open

Hampton Bays

Weston B.

includes taxes & fees

10 Jun - 11 Jun

Private One-Bedroom Cottage

Waterford

includes taxes & fees

12 Jun - 13 Jun

Town walking distance-Bridgehampton Cottage

Bridgehampton

Jim M.

includes taxes & fees

19 Jun - 20 Jun

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Top Shelter Island Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

6/10 Okay

"Great location, excellent facilities. Staff very mixed - some incredible and some terrible. Cumulative number of issues but dealt with by a member of the management team after getting fed up of a number of things, Including: Dog mess left for > 24 hours after reporting it. Staff member laughed and clearly did nothing after reporting it. Not our dog. Had to call 4 times to get our daughters bed made up in the room. Despite being on the booking months in advance. Asked for an ice cream for our daughter and told i was lying when i said they’d done it for her the two proceeding days and they couldnt get her one. Not the kind of treatment or experience from a resort of this quality."

The Bentley Hotel Southampton

10/10 Excellent

"The room was clean and nice. Having 4 kids with us it was upsetting that the ac in the living room didn’t work and the shower head was not functioning properly and had very low water pressure. There’s 2 tvs but only 1 remote was provided. Other than the few things we enjoyed our stay."

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