Shelter Island Cottages

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Our top choices for Shelter Island cottages

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton

Rob C.

includes taxes & fees

31 May - 1 June

North Fork Resort

Greenport

James

includes taxes & fees

1 June - 2 June

Beach Cottage, private beach and pass

East Lyme

Kerri G.

includes taxes & fees

3 June - 4 June

Seabreeze #3 Cozy Cottage steps to the beach

Hampton Bays

includes taxes & fees

31 May - 1 June

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

Waterford

Dianne B.

includes taxes & fees

9 June - 10 June

Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

Westbrook Center

Kate G.

includes taxes & fees

30 May - 31 May

Boutique 3-bedroom cottage, 2 separate units located in Waterford close to beach

Waterford

includes taxes & fees

4 June - 5 June

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Old Saybrook Center

Joyce S.

includes taxes & fees

2 June - 3 June

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Top Shelter Island Hotel Reviews

The Bentley Hotel Southampton

10/10 Excellent

"Really nice place to stay - recommend it every much"

Ocean Surf Resort

2/10 Terrible

"Sketchy. The room was clean & beautiful view. BUT, no one was on-staff to check me in when I arrived around 7pm. Keys were left in mailbox, ok. Not the worst part. Only 1 car there other than me when I arrived. Door only had a chain lock, no peephole to hallway, sliding door to ocean balcony didn’t lock & was only “secured” by a thin 1”w x .25” d piece of wood. 1 guy pulled up & sat in his vehicle for hours at night & best part, I found a CAMERA IN THE AC UNIT!!!! Definitely unsafe for females!!! Non-refundable of course so they can keep my $440 but I did not stay there. Went back the next night just to check & that same guy was in his car again! I paid for another hotel! BEWARE! Just a heads up."

Montauk Manor

6/10 Okay

"The grounds are beautiful and in the lobby are beautiful reminds you of old Spanish building. The rooms need major updating. The beds are uncomfortable and the pillows too. We found a few ants in bathroom. The did supply free car service to anyplace you were going which we liked. The bartender John at Monte’s was true gentleman. Made great drinks and gave us a history lesson about the place and montauk"

Gurney's Montauk Resort & Seawater Spa

4/10 Poor

"major construction would be ongoing for three of our four days at the hotel. Had we been informed beforehand, we would have made different arrangements entirely. The first room we were assigned had multiple issues: The AC was not functioning, and the room was 80 degrees upon arrival. The “ocean view” room primarily overlooked the parking lot, where delivery and work trucks created noise throughout the day. The door hinge was broken, leaving visible openings to the outside where bugs could enter. We attempted to contact the front desk to request a room change but were unable to get through initially and received no callback. After calling again two hours later, we were told someone would bring new room keys. Thirty minutes passed with no follow-up, and when I called again, the front desk member appeared unaware of the situation entirely but was able to send someone. While we appreciated being moved, the second room also felt poorly maintained, with visible grime on the side table and floor. At that point, we did not want to continue complaining so did not raise the issue. Additionally, despite my emailed request ahead of arrival (below), there were no extra pillows in either room to support my pregnancy. Unfortunately, the issues extended throughout the property: The gym was incredibly warm, construction noise was so loud it could be heard through noise-canceling headphones, and three of the five treadmills were out of service. The fire pit and shared outdoor areas were d"

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