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Check availability on Shelter Island 4 Star Hotels

Next weekend
Aug 7 - Aug 9
In two weeks
Aug 14 - Aug 16

Our top choices for Shelter Island 4-star hotels

2 restaurants; breakfast, lunch, and dinner served

1. Montauk Yacht Club

Montauk Yacht Club
4.5 star property
Montauk
8.6 out of 10, Excellent, (1,001 reviews)
"Truly amazing stay! Can’t wait to come back"
United States
Alexandra
The price is ￥92,079
￥123,165 total
includes taxes & fees
Aug 31 - Sep 1
Montauk Yacht Club
Resort view

2. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (673 reviews)
"Beautiful location, adequate facility and room to enjoy location"
United States
Dan
The price is ￥63,605
￥86,158 total
includes taxes & fees
Aug 13 - Aug 14
Sound View Greenport
Exterior

3. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.4 out of 10, Very Good, (839 reviews)
"Great property and great staff!"
United States
John
The price is ￥158,108
￥216,768 total
includes taxes & fees
Sep 1 - Sep 2
Gurney's Montauk Resort & Seawater Spa
Courtyard Balcony King | Courtyard view

4. Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (263 reviews)
"Highly recommend"
Australia
Jasmin
The price is ￥96,312
￥141,506 total
includes taxes & fees
Aug 31 - Sep 1
Marram
Terrace/patio

5. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (95 reviews)
"Stunning hotel! Will def stay again!"
United States
Anna
The price is ￥98,968
￥124,378 total
includes taxes & fees
Aug 31 - Sep 1
The Pridwin Hotel
Ocean View 2 Queens | Premium bedding, down comforters, pillowtop beds, blackout drapes

6. Offshore Montauk

Offshore Montauk
4.0 star property
Montauk
9.4 out of 10, Exceptional, (168 reviews)
"Beautiful hotel, location and amenities. We loved it here and will definitely be back."
United States
Jaime
The price is ￥76,157
￥104,993 total
includes taxes & fees
Aug 19 - Aug 20
Offshore Montauk
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas

7. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (300 reviews)
"Great location in the heart of town Walk to everything Amazing breakfast too "
United States
Michael
The price is ￥153,465
￥192,866 total
includes taxes & fees
Aug 3 - Aug 4
Faraway Sag Harbor
View from room

8. Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (229 reviews)
The price is ￥78,597
￥105,802 total
includes taxes & fees
Aug 4 - Aug 5
Hero Beach Club
Exterior

9. Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (379 reviews)
"Wonderful in every way."
United States
Meg
The price is ￥73,485
￥84,508 total
includes taxes & fees
Aug 23 - Aug 24
Madison Beach Hotel
Property entrance

10. The Maidstone

The Maidstone
4.0 star property
East Hampton
8.2 out of 10, Very Good, (167 reviews)
"It was very fantastic and the staff was very helpful. Late last night, my companion had need of feminine products and the staff was able to assist by giving her own. She was a lifesaver."
United States
Min
The price is ￥101,287
￥121,506 total
includes taxes & fees
Aug 31 - Sep 1
The Maidstone
Beach bar

11. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (161 reviews)
"This was my first time in the North fork and this hotel was a total surprise It was absolutely wonderful The accommodations the service the food everything was a delight and we cannot wait to come back"
United States
Sol
Silver Sands Motel & Beach Bungalows
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

12. Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
4.0 star property
Hampton Bays
9.8 out of 10, Exceptional, (68 reviews)
"Very beautiful hotel .no complains"
United States
Jason
Canoe Place Inn and Cottages
Breakfast and dinner served

13. Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (523 reviews)
"Stay was pricey, building on outside could use a little maintenance, bar and Restaurant was fantastic!"
United States
Gregg
The price is ￥43,915
￥50,502 total
includes taxes & fees
Aug 10 - Aug 11
Copper Beech Inn
Outdoor pool

14. Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (155 reviews)
"Incredible stay. Going back in the fall"
United States
Adam
The price is ￥152,016
￥174,230 total
includes taxes & fees
Aug 3 - Aug 4
Topping Rose House
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

15. Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (3 reviews)
"What a memorable way to celebrate America’s 250th Anniversary and the Fourth of July at Offshore Montauk. The festive atmosphere, beautiful weather, beach days, and fireworks made for an unforgettable getaway. The property is beautifully designed with thoughtful room layouts, high-end appliances, and quality finishes that create a luxurious yet comfortable experience. The attention to detail throughout the property is impressive, and it's exciting to see the continued improvements being...
United States
Frank
The price is ￥139,677
￥177,563 total
includes taxes & fees
Aug 3 - Aug 4
Offshore Spa & Residences
Beach nearby, white sand, sun loungers, beach umbrellas

16. The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
9.8 out of 10, Exceptional, (98 reviews)
"Fantastic hotel, great location."
United States
Tunca
The price is ￥187,895
￥225,406 total
includes taxes & fees
Sep 1 - Sep 2
The Roundtree, Amagansett
Villa, 3 Bedrooms, Pets Allowed, Pool View | Exterior

17. Serenity at Shorewood

Serenity at Shorewood
4.0 star property
East Hampton
Serenity at Shorewood
Miss Anna James Room | Iron/ironing board, WiFi (free), individually decorated

18. James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.2 out of 10, Wonderful, (26 reviews)
"Great location for an overnight stay"
United States
Diane
James Pharmacy Bed & Breakfast
Reception hall

19. 434 on Main

434 on Main
4.0 star property
Amagansett North
10.0 out of 10, Exceptional, (38 reviews)
"Great hosts"
United States
David
434 on Main
Outdoor dining

20. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (171 reviews)
"Beautiful property, we had a wonderful stay. Staff were very friendly and helpful, and the location is an easy walk to shops and restaurants."
United States
Lisa
The 1770 House Restaurant & Inn
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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 ￥156,613 per night from Aug 5 to Aug 6
￥156,613
￥260,470 total
Aug 5 - Aug 6
includes taxes & fees
9/10 Wonderful! (88 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
A wooden gazebo by a pond with a large tree trunk nearby.

Top Shelter Island Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

8/10 Good
"It’s Montauk, you go here for the beach, but if you also like to dip in a pool, it’s inconvenient, plan on walking an entire trail through a parking lot to get to it. I had a prime spot for a room, choose wisely, if it’s not beachfront, you’ll also walk. It’s Gurney’s, known for its spa, it’s truly the best part of the resort, beautiful and services are fine. The staff is very nice here but SLOW. I wouldn’t say in this case you get what you pay for, if you’re looking for a Montauk vacation you’re paying for the name if you’re going for the spa you’re also paying for the spa and personally, it’s not a family vacation spot, no activities. It’s definitely a tourist spot. Dog friendly, plan to hear dogs barking."
Jamie 2-night trip
Posted 1 day ago
Gurney's Montauk Resort & Seawater Spa

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 ￥260,470

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.