Shelter Island Cottages

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Our top choices for Shelter Island cottages

A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

1. North Fork Resort

Greenport

Altynai

includes taxes & fees

1 Nov - 2 Nov

A deck with a gray sofa, a wooden chair, and a metal fire pit.

2. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Greenport

Jeannette M.

includes taxes & fees

10 Nov - 11 Nov

A residential area with houses, a driveway, and a body of water in the background.

3. Steps to the beach | Seabreeze Cottage #3

Hampton Bays

"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

includes taxes & fees

1 Nov - 2 Nov

A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

4. 1-bedroom cottage with Grove Beach 🏖️ access.

Clinton

JM B.

includes taxes & fees

1 Nov - 2 Nov

A two-story house with a porch, a mailbox, and a lawn.

5. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Madison

Samantha D.

includes taxes & fees

4 Nov - 5 Nov

A white cottage with a front door, a garage, and a small porch with a potted plant.

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

Clinton

Wink V.

includes taxes & fees

2 Nov - 3 Nov

A single-story house with a gabled roof, a front porch, and a well-maintained garden.

7. Walk to Beach | Seabreeze Cottage #4

Hampton Bays

Weston B.

includes taxes & fees

8 Nov - 9 Nov

A small, single-story house with a white porch and a wooden front door.

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

Waterford

Jenna K.

includes taxes & fees

29 Nov - 30 Nov

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Top Shelter Island Hotel Reviews

Montauk Blue Hotel

8/10 Good

"Hard to get to beach but understandable"

Sun N Sound

10/10 Excellent

"I loved it here. The suite I stayed in was clean and the was no issue with parking. The back sitting area was right on the water which was amazing to watch the sunset. I really enjoyed my time at this property. You need a car or uber because nothing was really walkable from here but it was nice to stay on the other side of town. Ill def be back there again!"

Montauk Yacht Club

10/10 Excellent

"The room we stayed in definitely needed maintenance. Frayed carpet edges, unaligned tiles, excessive caulking, calcium buildup, etc. but it was spacious and aesthetically pleasing. However the stay was so relaxing and beautiful even in October. The view was just gorgeous and all the staff was extremely helpful and pleasant. As a nontraditional couple I was extremely pleased with the positive treatment we received. The grounds were well maintained and the spa was amazing. I just got glowing reviews from the people who received the massages and the masseuse really cares for her craft. The food was really fresh and filling. The smoothies were amazing and the vodka pasta met the hype from the reviews. It was an extremely relaxing stay with beautiful views. Will come again."

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