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Search Country Houses in Shelter Island

Check prices for these dates

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov
In one month
27 Nov - 29 Nov
In two months
25 Dec - 27 Dec
No exact matches found, but these alternatives could be just right

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 Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (75 reviews)
"Friendly staff , Unique property."
United States
Patrick
The price is £144
includes taxes & fees
19 Nov - 20 Nov
The Chequit
A serene landscape with a calm body of water reflecting trees with autumn foliage.

2. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (87 reviews)
"Such a cute place to stay! Bill was super kind and helpful! I was only in for a quick night but I would definitely stay here again!!"
United States
Tracey
The price is £159
includes taxes & fees
2 Nov - 3 Nov
House on Chase Creek
A beachside outdoor seating area with white Adirondack chairs and a fire pit.

3. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (186 reviews)
"Nicely renovated and enjoyable."
United States
Becky
The price is £197
includes taxes & fees
1 Nov - 2 Nov
Silver Sands Motel & Beach Bungalows
Front of property – evening/night

4. Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (66 reviews)
"What a beautiful hotel , clean , quiet , charming . We had a dip in the pool and enjoyed the coffee before we took ferry to sag harbor . The staff was amazing and very helpful throughout our stay. Highly recommended!"
United States
Kate
The price is £222
includes taxes & fees
31 Oct - 1 Nov
Shelter Island House
The entrance to The Harbor Front Inn with a double door and the address number 209.

5. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (669 reviews)
"Such a lovely place for a getaway. Charming town and lovely water views!"
United States
Laura
The price is £134
includes taxes & fees
18 Nov - 19 Nov
The Harbor Front Inn
A two-story house with a balcony, outdoor seating area, and a variety of plants.

6. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (440 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
The price is £141
includes taxes & fees
5 Nov - 6 Nov
Zey Hotel
A cozy interior with a bar area, seating, and a fireplace.

7. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (300 reviews)
"incredible stay, pet friendly and very accommodating. Staff was so kind!"
United States
Allison
The price is £201
includes taxes & fees
15 Nov - 16 Nov
Oyster Estate
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

8. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (194 reviews)
"Very clean, excellent staff and excellent location. All of the shops and restaurants are within walking distance, and the wineries a very short cab ride. Really enjoyed staying here and we will absolutely be back."
United States
Daniel
The price is £312
includes taxes & fees
8 Nov - 9 Nov
The Menhaden
A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

9. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (349 reviews)
"Very clean property, beautiful view, and quiet."
United States
Masayo
The price is £160
includes taxes & fees
10 Nov - 11 Nov
The Shoals Suites and Slips
A modern interior with a central water feature, shelves with products, and a clothing rack.

10. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (208 reviews)
"Great location, very friendly and helpful "
United States
Mary
The price is £245
includes taxes & fees
2 Nov - 3 Nov
American Beech Hotel
A spacious room with wicker furniture, large windows, and a view of the sea.

11. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (762 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
The price is £152
includes taxes & fees
15 Nov - 16 Nov
Sound View Greenport
A modern house with a deck, outdoor seating, and a fire pit.

12. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (71 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is £266
includes taxes & fees
8 Nov - 9 Nov
North Fork Resort
A balcony with a view of the ocean, a lawn, and a house in the background.

13. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is £228
includes taxes & fees
12 Nov - 13 Nov
Cliffside Resort Condominiums
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

14. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (681 reviews)
"Free parking, clean, continental breakfast good quality."
United States
Terri
The price is £188
includes taxes & fees
2 Nov - 3 Nov
Sag Harbor Inn
A pool area with umbrellas, potted plants, and a pathway leading to a building.

15. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (319 reviews)
"Great location , wonderful lobby bar Cute rooms"
United States
Thomas
The price is £301
includes taxes & fees
18 Nov - 19 Nov
Faraway Sag Harbor
A metal compass sign with the words "AQUA VISTA GREENPORT" on a building's exterior wall.

16. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is £188
includes taxes & fees
18 Nov - 19 Nov
Aqua Vista
A two-story house with a white staircase, a covered patio with outdoor furniture, and a fenced yard.

17. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is £179
includes taxes & fees
8 Nov - 9 Nov
Harbor Heights
A covered patio with outdoor furniture, a door, and a view of a residential area.

18. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is £179
includes taxes & fees
10 Nov - 11 Nov
The SandPiper
A porch with a white railing, a small blue house decoration, and a 'Gone' sign.

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

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (35 reviews)
"We had a great stay!! "
United States
Callie E.
The price is £271
includes taxes & fees
2 Nov - 3 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A small, single-story house with a gabled roof, a front door, and a number "401" on the door.

20. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is £321
includes taxes & fees
3 Nov - 4 Nov
Beach Block Hideaway
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.
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Top Shelter Island Hotel Reviews

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Great location, great service."
Julian 1-night trip
Posted 15 hours ago
Hyatt Place Long Island East End

Find out more about Shelter Island

Shelter Island Country Houses information

Number of reviews
2,992
Accommodation
2 Country Houses
Lowest Price
£134
Highest Price
£321