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Find 4 Star Hotels in Shelter Island, NY from ￥33,512

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Check availability on Shelter Island 4 Star Hotels

Tonight
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
This weekend
Oct 3 - Oct 5
Next weekend
Oct 10 - Oct 12

Compare Shelter Island 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Montauk Yacht Club
Indoor pool, 2 outdoor pools

Montauk Yacht Club

4.0 star property
8.6 out of 10, Excellent, (1011)
"Wonderful hotel and location "
Montauk Yacht Club
Sound View Greenport
Seasonal outdoor pool, pool umbrellas, sun loungers

Sound View Greenport

4.0 star property
8.4 out of 10, Very Good, (574)
"Loved everything about my stay at the Sound view !! "
The price is ￥37,099
￥49,702 total
includes taxes & fees
Oct 27 - Oct 28
Sound View Greenport
Gurney's Montauk Resort & Seawater Spa
Outdoor wedding area

Gurney's Montauk Resort & Seawater Spa

4.0 star property
8.2 out of 10, Very Good, (669)
"Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay. "
The price is ￥60,745
￥82,908 total
includes taxes & fees
Sep 30 - Oct 1
Gurney's Montauk Resort & Seawater Spa
Marram
Seasonal outdoor pool, pool umbrellas, sun loungers

Marram

4.0 star property
8.8 out of 10, Excellent, (228)
"We loved everything about our stay here: the beds are comfortable, the fire pits with the smores are a nice touch, the beach is very nice, the view as well; and the food is amazing. The staff is very helpful and friendly!"
The price is ￥30,253
￥48,228 total
includes taxes & fees
Oct 13 - Oct 14
Marram
Baron's Cove
Front of property - evening/night

Baron's Cove

4.0 star property
9.0 out of 10, Wonderful, (289)
"staff seemed tired and fed up of people staying!"
Baron's Cove
The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, sun loungers

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (79)
"Shelter Island is definitely a gem"
The Pridwin Hotel
Journey East Hampton
Exterior

Journey East Hampton

4.0 star property
9.0 out of 10, Wonderful, (149)
"We had a good stay at The Journey. Can’t wait to come back! "
Journey East Hampton
Hero Beach Club
View from room

Hero Beach Club

4.0 star property
9.0 out of 10, Wonderful, (193)
"Great service and location. Definitely will be back."
The price is ￥22,604
￥33,512 total
includes taxes & fees
Oct 21 - Oct 22
Hero Beach Club
Silver Sands Motel & Beach Bungalows
Beach bar

Silver Sands Motel & Beach Bungalows

4.0 star property
9.8 out of 10, Exceptional, (129)
"We had a great time, it’s a beautiful property and there’s plenty to do downtown. It was our first time here and we’ll definitely be back. "
Silver Sands Motel & Beach Bungalows
Madison Beach Hotel
Exterior

Madison Beach Hotel

4.0 star property
9.4 out of 10, Exceptional, (319)
"the staff was exceptional and our dinner was very good"
The price is ￥50,700
￥58,305 total
includes taxes & fees
Oct 27 - Oct 28
Madison Beach Hotel
Canoe Place Inn and Cottages
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Canoe Place Inn and Cottages

4.0 star property
9.8 out of 10, Exceptional, (58)
"Amazing property. Really enjoyed our stay."
Canoe Place Inn and Cottages
Topping Rose House
Outdoor pool

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (135)
"Great rooms, staff and food"
The price is ￥65,933
￥75,851 total
includes taxes & fees
Oct 1 - Oct 2
Topping Rose House
Copper Beech Inn
Breakfast and dinner served

Copper Beech Inn

4.0 star property
8.6 out of 10, Excellent, (504)
"Had a fantastic room 324 in the newer building.. Breakfast was delicious and service terrific.."
The price is ￥41,708
￥47,964 total
includes taxes & fees
Oct 1 - Oct 2
Copper Beech Inn
The Roundtree, Amagansett
Beach nearby, white sand, sun loungers, beach umbrellas

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (88)
"The Roundtree was one of the most peaceful hotels we’ve ever stayed in. I highly recommend for a romantic getaway. "
The price is ￥88,947
￥106,703 total
includes taxes & fees
Oct 1 - Oct 2
The Roundtree, Amagansett
The 1770 House Restaurant & Inn
Garden

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (157)
"The staff was incredibly genuine and the property felt intimate and comfortable."
The price is ￥48,584
￥66,419 total
includes taxes & fees
Oct 2 - Oct 3
The 1770 House Restaurant & Inn
The Maidstone
Front of property - evening/night

The Maidstone

4.0 star property
8.0 out of 10, Very Good, (148)
"We had a wonderful stay "
The Maidstone
James Pharmacy Bed & Breakfast
Miss Anna James Room | Individually decorated, individually furnished, iron/ironing board

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (18)
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
The price is ￥40,640
￥45,111 total
includes taxes & fees
Oct 1 - Oct 2
James Pharmacy Bed & Breakfast
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (64)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
The price is ￥56,776
￥64,866 total
includes taxes & fees
Oct 27 - Oct 28
East Hampton Art House Bed & Breakfast
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
10.0 out of 10, Exceptional, (1)
Canoe Place Waterfront Residences
Offshore Residences
One Bedroom Condo King with Steam Shower | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

Offshore Residences

4.0 star property
The price is ￥79,080
￥107,428 total
includes taxes & fees
Oct 19 - Oct 20
Offshore Residences
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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 ￥41,110 per night from Oct 27 to Oct 28
￥41,110
￥51,664 total
Oct 27 - Oct 28
includes taxes & fees
9/10 Wonderful! (70 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
Great shot of Sunset Beach on Shelter Island from our boat, before heading closer to anchor and swim in. A beautiful little slice of Southern France right here on Long Island Sound! If you get a chance, definitely check this place out.
Photo by tom owens
Open Photo by tom owens

Top Shelter Island Hotel Reviews

Marram

Marram

10/10 Excellent
"Locations are d writhing, and the marran has this, right on the beach, watching whales, dolphins and spinning sharks from the comfort of the pool and/or beach…… lovely sitting area for drinks and dinner watching the sun go down. This is a hotel to savour on a nice night, we stayed the 18/19 sept, 2025! One thing that was a shock, no TV in room and little hanging space for clothes, so if you can manage around that (as we did) The other odd point and the reason for my low score on Eco friendly, is the hotels use of plastic fork, knives and spoons, and plastic cups which in this day goes against the grain, so that aside if you want a modern hotel in a great location thus is a must……. And one, that we would go back too."
Ian 1-night trip
Posted 9 days ago
Marram

Frequently asked questions

What are the best 4-star hotels in Shelter Island?
Make unforgettable memories in Shelter Island at Topping Rose House. A favorite 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 ￥51,664

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.

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