Photo by tom owens

Compare and book 4 Star hotels in Shelter Island, New York

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Check availability on Shelter Island 4 Star Hotels

Tonight
26 Jun - 27 Jun
Tomorrow
27 Jun - 28 Jun
This weekend
27 Jun - 29 Jun
Next weekend
4 Jul - 6 Jul

Top Shelter Island 4 Star Hotels

Montauk Yacht Club
Indoor pool, 2 outdoor pools

Montauk Yacht Club

4.0 star property
8.6 out of 10, Excellent, (1005)
"Loved the cleanliness, views, and amenities "
Montauk Yacht Club
Gurney's Montauk Resort & Seawater Spa
Ocean View One Bedroom Suite | Premium bedding, in-room safe, iron/ironing board, free rollaway beds

Gurney's Montauk Resort & Seawater Spa

4.0 star property
8.2 out of 10, Very good, (639)
"Gurneys Inn was a beautiful place to stay. The staff extremely attentive and friendly!"
The price is 24.187.825 ₫
33.012.392 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Gurney's Montauk Resort & Seawater Spa
Baron's Cove
Front of property – evening/night

Baron's Cove

4.0 star property
9.0 out of 10, Wonderful, (255)
"Great location in the heart of town Walk to everything Amazing breakfast too "
The price is 8.426.478 ₫
10.590.090 ₫ total
includes taxes & fees
13 Jul - 14 Jul
Baron's Cove
Marram
Seasonal outdoor pool, pool umbrellas, pool loungers

Marram

4.0 star property
8.6 out of 10, Excellent, (167)
"Beautiful property, with direct access to"
The price is 9.510.685 ₫
15.796.814 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Marram
Silver Sands Motel & Beach Bungalows
Waterfront Beach Shack Studio | 1 bedroom, premium bedding, down duvets, pillow-top beds

Silver Sands Motel & Beach Bungalows

4.0 star property
9.8 out of 10, Exceptional, (98)
"The rooms were remodeled and well decorated. The restaurant was amazing."
Silver Sands Motel & Beach Bungalows
Sound View Greenport
Seasonal outdoor pool, pool umbrellas, pool loungers

Sound View Greenport

4.0 star property
8.4 out of 10, Very good, (531)
"We had an overall great stay and will be back. Especially loved nights out on the beach!"
The price is 11.091.098 ₫
14.015.901 ₫ total
includes taxes & fees
27 Jul - 28 Jul
Sound View Greenport
Canoe Place Inn and Cottages
Garden

Canoe Place Inn and Cottages

4.0 star property
10.0 out of 10, Exceptional, (43)
"The staff were super nice and accommodating. This place beautiful & clean. Really enjoyed our stay. "
Canoe Place Inn and Cottages
Journey East Hampton
Exterior

Journey East Hampton

4.0 star property
9.0 out of 10, Wonderful, (138)
"Great property! Staff is great and personable. I’ve stayed multiple times and will definitely be back again. "
The price is 11.652.943 ₫
14.644.879 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Journey East Hampton
The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, pool loungers

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (61)
"Lovely hotel/ resort. Look forward to going again!"
The price is 10.244.263 ₫
12.874.501 ₫ total
includes taxes & fees
14 Jul - 15 Jul
The Pridwin Hotel
Hero Beach Club
View from room

Hero Beach Club

4.0 star property
9.0 out of 10, Wonderful, (170)
"Excellent Motel. My only recommendation is they need to put towel racks in the bathroom."
The price is 10.475.878 ₫
14.508.796 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Hero Beach Club
Madison Beach Hotel
Front of property – evening/night

Madison Beach Hotel

4.0 star property
9.4 out of 10, Exceptional, (296)
"I loved everything about the property "
The price is 11.761.495 ₫
13.525.720 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Madison Beach Hotel
Offshore Montauk
1 bedroom, pillow-top beds, laptop workspace, blackout curtains

Offshore Montauk

2.0 star property
8.6 out of 10, Excellent, (4)
"We were the first guests on opening day and had a wonderful stay. Staff was very attentive, the location is perfect—steps from the beach with chairs and towels provided, and walking distance to shops. We’ll definitely be back!"
The price is 9.837.648 ₫
14.227.949 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Offshore Montauk
The Maidstone
Front of property – evening/night

The Maidstone

4.0 star property
8.0 out of 10, Very good, (136)
"I loved the look of the grounds! "
The price is 18.715.334 ₫
21.382.040 ₫ total
includes taxes & fees
6 Jul - 7 Jul
The Maidstone
The Roundtree, Amagansett
Free daily continental breakfast

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (86)
"Fantastic hotel, great location."
The price is 33.862.955 ₫
40.622.928 ₫ total
includes taxes & fees
6 Jul - 7 Jul
The Roundtree, Amagansett
Copper Beech Inn
Breakfast and dinner served

Copper Beech Inn

4.0 star property
8.6 out of 10, Excellent, (497)
"Tired, expensive needs update"
The price is 7.295.571 ₫
8.389.907 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Copper Beech Inn
The 1770 House Restaurant & Inn
Reception

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (153)
"We had a fantastic stay!!! Thank you "
The price is 13.532.108 ₫
18.499.372 ₫ total
includes taxes & fees
29 Jun - 30 Jun
The 1770 House Restaurant & Inn
Topping Rose House
Outdoor pool

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (133)
"Had an excellent stay at Topping Rose House! Can’t wait to be back soon!"
The price is 28.641.915 ₫
32.814.938 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Topping Rose House
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
The price is 52.167.255 ₫
63.177.225 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Canoe Place Waterfront Residences
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (61)
"The hosts were really nice and the breakfast is excellent!"
The price is 26.619.682 ₫
30.413.117 ₫ total
includes taxes & fees
1 Jul - 2 Jul
East Hampton Art House Bed & Breakfast
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Shelter Island.
Mill House Inn

Mill House Inn

31 North Main Street, East Hampton, NY
The price is 26.018.255 ₫ per night from 7 Jul to 8 Jul
26.018.255 ₫
32.698.279 ₫ total
7 Jul - 8 Jul
includes taxes & fees
9/10 Wonderful! (69 reviews)
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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.

Learn more about Shelter Island

Nestled between Long Island's forks, this serene island offers pristine beaches and kayaking through Mashomack Preserve's coastal wetlands. Rent bikes to explore historic mansions and stop at Sunset Beach for seafood with spectacular evening views across Shelter Bay.

See all hotels in Shelter Island
Photo by tom owens
Open Photo by tom owens

Frequently asked questions

What are the best 4-star hotels in Shelter Island?
Make unforgettable memories in Shelter Island at Topping Rose House. A favourite with Expedia customers, this 4-star hotel offers loads of conveniences for a relaxing and comfortable stay.
How much does it cost to stay in a 4-star hotel in Shelter Island?
To lock in a 4-star hotel in Shelter Island that fits your budget, make use of Expedia's filters. Check out what's available during your preferred dates and use our pricing filter to set your maximum rate. You can also sort your results by the most economical option first.
  • Search for the lowest price from 26.018.255 ₫

What's the difference between 5-star and 4-star hotels in Shelter Island?
Treat yourself to luxury living during your Shelter Island getaway by choosing a 4-star hotel. As well as featuring upscale surroundings, these properties are typically packed with amenities such as large beds, complimentary bathrobes and plenty more. A 5-star hotel will go the extra mile to make your trip an even more lavish and memorable one. 24-hour concierge assistance, elegant décor and world-class dining are only the start of the exclusive conveniences and services you'll likely get access to.