Four Star Hotels in Shelter Island

Most hotels are fully refundable. Because flexibility matters.

Save an average of 15% on thousands of hotels with Expedia Rewards

Search over 2.9 million properties and 550 airlines worldwide

Top Shelter Island 4 Stars Hotels

Seasonal outdoor pool, pool umbrellas, pool loungers
Canoe Place Inn and Cottages
4.0 star property
10.0 out of 10, Exceptional, (26)
"Absolutely the nicest hotel in the area. "
The price is RM 2,346
per night
12 May - 13 May
Canoe Place Inn and Cottages
Reception hall
434 on Main
4.0 star property
10.0 out of 10, Exceptional, (34)
"Great hosts"
434 on Main
Beach nearby, white sand, sun-loungers, beach umbrellas
The Roundtree, Amagansett
4.5 star property
9.8 out of 10, Exceptional, (75)
"The best hotel in the Hamptons! Luxury hospitality without pretension. Quiet, simple and the only one worth the price tag. You will pay the same if not more at any other local hotel and receive the worst service. It would be so easy for Roundtree to just rely on the high summer months to make money and rob you because they can, but they don't. The whole team works with an integrity uncommon to the area. Easy walk to everything in town and while they don't have a restaurant or bar they make up...
The price is RM 2,820
per night
12 May - 13 May
The Roundtree, Amagansett
Save an average of 15% on thousands of hotels when you're signed in
Reception
The 1770 House Restaurant & Inn
4.0 star property
9.8 out of 10, Exceptional, (135)
"beautiful inn with a scenic setting"
The price is RM 1,398
per night
22 May - 23 May
The 1770 House Restaurant & Inn
Aerial view
East Hampton Art House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (53)
"Beautiful property and Michael and Rosealind are some the nicest hosts we have ever encountered. "
The price is RM 1,972
per night
13 May - 14 May
East Hampton Art House Bed & Breakfast
Food and drink
Jedediah Hawkins Inn
4.0 star property
9.8 out of 10, Exceptional, (18)
"We had a wonderful stay. The accommodations and services was outstanding and the property was absolutely beautiful. I have already recommended the hotel to my coworkers and family and will definitely be visiting again! "
Jedediah Hawkins Inn
Front of property – evening/night
Madison Beach Hotel
4.0 star property
9.4 out of 10, Exceptional, (243)
"The staff was extremely courteous and professional. Location ideal."
The price is RM 1,337
per night
14 May - 15 May
Madison Beach Hotel
Outdoor pool
Topping Rose House
4.5 star property
9.4 out of 10, Exceptional, (105)
"Noise from other guests."
The price is RM 2,820
per night
12 May - 13 May
Topping Rose House
Indoor pool, seasonal outdoor pool, pool loungers
The Baker House 1650
4.5 star property
9.4 out of 10, Exceptional, (32)
"Absolutely best place to stay in East Hampton! Charming B&B with incredible staff. "
The price is RM 2,180
per night
20 May - 21 May
The Baker House 1650
Garden
James Pharmacy Bed & Breakfast
4.0 star property
9.4 out of 10, Exceptional, (7)
"quiet and safe, close to everything yet off the 'main' part of the road. bright and airy, loved the room and decor was gorgeous. we were already at the beach, didn't need to see more beach decor. pass to harveys beach was nice, but the beach was gross. breakfast voucher was great, restaurant was quick and delicious"
The price is RM 1,355
per night
12 May - 13 May
James Pharmacy Bed & Breakfast
View from room
Hero Beach Club
4.0 star property
9.0 out of 10, Wonderful, (139)
"Room was clean, comfortable, nicely done. The hotel is close to the beach, walking distance to town. Alex was very nice and helpful, we enjoyed our stay and would definitely come back."
The price is RM 972
per night
12 May - 13 May
Hero Beach Club
Exterior
Journey East Hampton
4.0 star property
8.8 out of 10, Excellent, (88)
"Loved the room, bed was comfortable, shower was lovely. Cindy gave great suggestions on where to go."
The price is RM 1,386
per night
27 May - 28 May
Journey East Hampton
Breakfast and dinner served
Copper Beech Inn
4.0 star property
8.6 out of 10, Excellent, (454)
"The room was large, very nice and clean. "
The price is RM 991
per night
12 May - 13 May
Copper Beech Inn
Lobby sitting area
Sound View Greenport
4.0 star property
8.4 out of 10, Very good, (426)
"Beautiful location. Staff was friendly and helpful. Dining was delicious. Rooms were renovated and spacious "
The price is RM 1,189
per night
16 May - 17 May
Sound View Greenport
Blackout curtains, iron/ironing board, free WiFi, bed sheets
Marram
4.0 star property
8.4 out of 10, Very good, (125)
"N/A"
The price is RM 1,540
per night
12 May - 13 May
Marram
Premium bedding, down duvets, minibar, in-room safe
Montauk Yacht Club
4.0 star property
8.4 out of 10, Very good, (946)
"Room and property were beautiful "
Montauk Yacht Club
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very good, (561)
"front desk staff irritating as can be "
The price is RM 2,112
per night
12 May - 13 May
Gurney's Montauk Resort & Seawater Spa
Front of property – evening/night
The Maidstone
4.0 star property
7.8 out of 10, Good, (112)
"Staff was very friendly and engaging. Handled all of our needs wonderfully."
The price is RM 3,768
per night
23 May - 24 May
The Maidstone
Living area
Villa Direen - Modern East Hampton Villa
4.0 star property
Villa Direen - Modern East Hampton Villa
Balcony
The Mainstay
4.0 star property
The Mainstay

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.
Still don't see what you're looking for?
See all properties in Shelter Island.
You can also use these popular filters to refine your search.
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.