Shelter Island Country Houses

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Recommended hotels in Shelter Island

A large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony.

1. The Chequit

The Heights

Patrick

includes taxes & fees

19 Nov - 20 Nov

A serene landscape with a calm body of water reflecting trees with autumn foliage.

2. House on Chase Creek

The Heights

Tracey

includes taxes & fees

2 Nov - 3 Nov

3. Shelter Island House

Shelter Island Heights

Kate

A two-story house with a balcony, outdoor seating area, and a variety of plants.

4. Zey Hotel

Greenport

sacha

includes taxes & fees

29 Oct - 30 Oct

A beachside outdoor seating area with white Adirondack chairs and a fire pit.

5. Silver Sands Motel & Beach Bungalows

Greenport

Gaurav

includes taxes & fees

1 Nov - 2 Nov

The entrance to The Harbor Front Inn with a double door and the address number 209.

6. The Harbor Front Inn

Greenport

Antrii

includes taxes & fees

16 Nov - 17 Nov

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

7. The Shoals Suites and Slips

Southold

Masayo

includes taxes & fees

29 Oct - 30 Oct

A spacious room with wicker furniture, large windows, and a view of the sea.

8. Sound View Greenport

Greenport

Christine

includes taxes & fees

22 Nov - 23 Nov

A balcony with a view of the ocean, a lawn, and a house in the background.

9. Cliffside Resort Condominiums

Greenport

William

includes taxes & fees

12 Nov - 13 Nov

A cozy interior with a bar area, seating, and a fireplace.

10. Oyster Estate

Greenport

Allison

includes taxes & fees

29 Oct - 30 Oct

A modern interior with a central water feature, shelves with products, and a clothing rack.

11. American Beech Hotel

Greenport

Mary

includes taxes & fees

1 Nov - 2 Nov

A covered patio with outdoor furniture, a door, and a view of a residential area.

12. The SandPiper

Pipes Cove

Manuela C.

includes taxes & fees

10 Nov - 11 Nov

A metal compass sign with the words "AQUA VISTA GREENPORT" on a building's exterior wall.

13. Aqua Vista

Pipes Cove

Kerri L.

includes taxes & fees

9 Nov - 10 Nov

A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

14. The Menhaden

Greenport

Daniel

includes taxes & fees

8 Nov - 9 Nov

A two-story house with a white staircase, a covered patio with outdoor furniture, and a fenced yard.

15. Harbor Heights

Pipes Cove

Steven R.

includes taxes & fees

3 Nov - 4 Nov

A modern house with a deck, outdoor seating, and a fire pit.

16. North Fork Resort

Greenport

Altynai

includes taxes & fees

1 Nov - 2 Nov

A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

17. Sag Harbor Inn

Sag Harbor

Terri

includes taxes & fees

1 Nov - 2 Nov

A porch with a white railing, a small blue house decoration, and a 'Gone' sign.

18. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Pipes Cove

Callie E.

includes taxes & fees

2 Nov - 3 Nov

19. American Beech in Greenport NY - King Suite 1

Greenport

Dean J.

A greenhouse with a checkered floor, a table with a lamp, and a potted plant.

20. American Beech in Greenport - King Suite 3

Greenport

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Top Shelter Island Hotel Reviews

Sun N Sound

10/10 Excellent

"Location, very clean, comfortable"

Zey Hotel

10/10 Excellent

"The stay was perfect. I can't think of a single thing to criticize. As an example, when we were checking out, we called the manager on his cell to alert him that a fire truck was flushing the street hydrants, and that we noticed that the water in the room was brown. We knew that the maintenance of the hydrants was causing the dirty water. The manager promptly told us we could stay until 6:00 pm for free, so that we would be able to take clean showers. We told him that we had showered early, and that we had no problem. But his response showed how he cared for the guests."

Saybrook Point Resort & Marina

10/10 Excellent

"A wonderful getaway. It was lovely. The room was beautiful with a fireplace they came and started for us. We had a balcony over looking the marina, and river. The sunrises were amazing. Great places to walk or take a resort bike. We were there in October and it was great. I will take out of season any day. Old Saybrook is a treasure."

Faraway Sag Harbor

8/10 Good

"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."

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