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Check prices for these dates

Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov
In one month
20 Nov - 22 Nov
In two months
18 Dec - 20 Dec
No exact matches found, but these alternatives could be just right

Recommended hotels in Shelter Island

An outdoor patio area with string lights, tables, chairs, and a fire pit.

1. The Chequit

The Chequit
3.0 star property
The Heights
9.2 out of 10, Wonderful, (69 reviews)
"Friendly staff , Unique property."
United States
Patrick
The price is NZ$335
includes taxes & fees
1 Nov - 2 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 NZ$372
includes taxes & fees
2 Nov - 3 Nov
House on Chase Creek
Front of property – evening/night

3. Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (66 reviews)
"This boutique hotel is a true gem. Set among lush trees and beautiful landscaping, and with excellent indoor space, it provides a welcoming and relaxing atmosphere."
United States
Dorothy
The price is NZ$405
includes taxes & fees
25 Oct - 26 Oct
Shelter Island House
A lakeside patio with outdoor seating and a view of the water.

4. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (179 reviews)
"This is a great place that brings you back to a special time. Staff were exceptionally friendly and helpful. Made us feel like we were family - highly recommend."
United States
Keith
The price is NZ$486
includes taxes & fees
1 Nov - 2 Nov
Silver Sands Motel & Beach Bungalows
A two-story house with a balcony, outdoor seating area, and a variety of plants.

5. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (434 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
The price is NZ$330
includes taxes & fees
29 Oct - 30 Oct
Zey Hotel
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

6. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (668 reviews)
"Great hotel with friendly staff, clean and comfortable rooms, and excellent service — I really enjoyed my stay!"
United States
Antrii
The price is NZ$410
includes taxes & fees
4 Nov - 5 Nov
The Harbor Front Inn
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

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (347 reviews)
"Very clean property, beautiful view, and quiet."
United States
Masayo
The price is NZ$417
includes taxes & fees
1 Nov - 2 Nov
The Shoals Suites and Slips
A spacious room with wicker furniture, large windows, and a view of the sea.

8. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (759 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
The price is NZ$411
includes taxes & fees
16 Nov - 17 Nov
Sound View Greenport
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.

9. 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 NZ$499
includes taxes & fees
25 Oct - 26 Oct
Oyster Estate
Terrace/patio

10. 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 NZ$536
includes taxes & fees
12 Nov - 13 Nov
Cliffside Resort Condominiums
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

11. 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 NZ$575
includes taxes & fees
25 Oct - 26 Oct
American Beech Hotel
A waterfront property with a large house, multiple boats docked, and lush greenery.

12. 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 NZ$441
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

13. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (192 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 NZ$732
includes taxes & fees
8 Nov - 9 Nov
The Menhaden
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

14. 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 NZ$437
includes taxes & fees
9 Nov - 10 Nov
Aqua Vista
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

15. 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 NZ$437
includes taxes & fees
10 Nov - 11 Nov
The SandPiper
A beach with people relaxing on chairs and sunbathing.

16. 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 NZ$416
includes taxes & fees
4 Nov - 5 Nov
Harbor Heights
A beach with people relaxing, a pier extending into the water, and a clear sky.

17. 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 wonderful stay in Greenport! The location was absolutely perfect, and one of the things we loved most was being able to walk to town and the beautiful harbor. Everything was so conveniently located, from the charming shops and wonderful restaurants to the lovely waterfront, making it easy to enjoy everything Greenport has to offer without needing to drive. We would happily stay here again and highly recommend this place to anyone looking for a wonderful Greenport getaway!"
United States
Nino
The price is NZ$625
includes taxes & fees
2 Nov - 3 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A pool area with umbrellas, potted plants, and a pathway leading to a building.

18. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (315 reviews)
"Great location , wonderful lobby bar Cute rooms"
United States
Thomas
The price is NZ$817
includes taxes & fees
16 Nov - 17 Nov
Faraway Sag Harbor
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

19. American Beech in Greenport - King Suite 3

American Beech in Greenport - King Suite 3
Greenport
The price is NZ$555
includes taxes & fees
26 Oct - 27 Oct
American Beech in Greenport - King Suite 3
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

20. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (604 reviews)
"great spot to stay,"
United States
Armando
The price is NZ$272
includes taxes & fees
31 Oct - 1 Nov
The Bentley Hotel Southampton
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

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Great property and view."
Trevor 2-night trip
Posted 14 hours ago
Montauk Yacht Club

Find out more about Shelter Island

Shelter Island Country House information

Number of reviews
3,742
Accommodation
2 Country House
Lowest Price
NZ$272
Highest Price
NZ$817