Find 4 Star Hotels in Shelter Island, NY from $195

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

Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very Good, (565)
"Amazing beds "
The price is $515
$703 total
includes taxes & fees
May 21 - May 22
Gurney's Montauk Resort & Seawater Spa
Lobby sitting area
Sound View Greenport
4.0 star property
8.4 out of 10, Very Good, (427)
"Beautiful location. Staff was friendly and helpful. Dining was delicious. Rooms were renovated and spacious "
The price is $251
$320 total
includes taxes & fees
May 19 - May 20
Sound View Greenport
Front of property - evening/night
Madison Beach Hotel
4.0 star property
9.4 out of 10, Exceptional, (244)
"Very special: comfortable and relaxing. Gorgeous views. Caring staff."
The price is $302
$347 total
includes taxes & fees
May 29 - May 30
Madison Beach Hotel
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Beachfront King | Blackout drapes, 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 $195
$405 total
includes taxes & fees
May 16 - May 17
Marram
Premium bedding, down comforters, minibar, in-room safe
Montauk Yacht Club
4.0 star property
8.4 out of 10, Very Good, (948)
"Beyond perfect! From the second we got there to the second we left. The hotel was so clean and the staff was so helpful. Not one bad thing to say. I cannot wait to come back. "
The price is $360
$484 total
includes taxes & fees
May 28 - May 29
Montauk Yacht Club
Outdoor pool
Topping Rose House
4.5 star property
9.4 out of 10, Exceptional, (105)
"Noise from other guests."
The price is $639
$733 total
includes taxes & fees
May 23 - May 24
Topping Rose House
Exterior
Journey East Hampton
4.0 star property
8.8 out of 10, Excellent, (88)
"We stayed in the cottage and it was very well appointed decor wise. Cute common areas where breakfast is. The room could have used another light in the LR and it needed a desk and a better closet. No place to put the luggage and tiny closet. Could be furnished a bit better to accomodate. Overall very nice stay. Tx!"
The price is $293
$367 total
includes taxes & fees
May 29 - May 30
Journey East Hampton
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 $205
$325 total
includes taxes & fees
May 16 - May 17
Hero Beach Club
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 $595
$713 total
includes taxes & fees
May 19 - May 20
The Roundtree, Amagansett
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 $209
$240 total
includes taxes & fees
May 16 - May 17
Copper Beech Inn
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 $295
$410 total
includes taxes & fees
May 22 - May 23
The 1770 House Restaurant & Inn
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
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 $500
$599 total
includes taxes & fees
May 22 - May 23
Canoe Place Inn and Cottages
Indoor pool, seasonal outdoor pool, sun 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 $460
$525 total
includes taxes & fees
May 20 - May 21
The Baker House 1650
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 $795
$907 total
includes taxes & fees
May 23 - May 24
The Maidstone
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 $762
$869 total
includes taxes & fees
May 16 - May 17
East Hampton Art House Bed & Breakfast
Reception hall
434 on Main
4.0 star property
10.0 out of 10, Exceptional, (34)
"Great hosts"
434 on Main
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 $286
$438 total
includes taxes & fees
May 16 - May 17
James Pharmacy Bed & Breakfast
Luxury Villa (6 Bedrooms) | Living area | TV
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
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

Explore similar 5-star hotels

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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.

Frequently asked questions

What are the best 4-star hotels in Shelter Island?
Expedia guests enjoy staying at Topping Rose House. From its handy amenities to its attentive staff, everything about this 4-star hotel in Shelter Island is designed to offer an awesome vacation experience.
How much does it cost to stay in a 4-star hotel in Shelter Island?
To find a 4-star hotel in Shelter Island that fits your budget, take advantage of Expedia’s filter tool. Check out what’s available during your chosen dates and use our pricing filter to set your limit. You can also sort your results by the most wallet-friendly stay first.

  • Search for the lowest price from $450

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 checking in to a 4-star hotel. As well as featuring upscale surroundings, these properties are typically packed with amenities like bathrobes, large beds and more. A 5-star hotel will go the extra mile to make your stay an even more indulgent and special one. Round-the-clock concierge assistance, luxurious spas and world-class dining are just the start of the superior conveniences and services you’ll likely be able to enjoy.
Does Shelter Island have any 4-star all-inclusive resorts?
Use our “All inclusive” filter to search for your dream resort in Shelter Island where everything is taken care of, from your accommodations to your food, activities and entertainment. We can also help you find standard 4-star stays in and around this sought-after destination.
Are there any 4-star casino hotels in Shelter Island?
Shuffle between your room and the roulette wheel with ease by using our filters to find 4-star casino hotels in and around Shelter Island. Celebrating with someone special? Refine your search further by selecting amenities with a wow-factor, like a hot tub or view.