Find 4 Star Hotels in Shelter Island, NY from $209

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, (570)
"Great time beautiful property"
The price is $526
$718 total
includes taxes & fees
May 30 - May 31
Gurney's Montauk Resort & Seawater Spa
Lobby sitting area
Sound View Greenport
4.0 star property
8.4 out of 10, Very Good, (428)
"Beautiful location. Staff was friendly and helpful. Dining was delicious. Rooms were renovated and spacious "
The price is $259
$331 total
includes taxes & fees
May 27 - May 28
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 $329
$378 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 $355
$588 total
includes taxes & fees
May 27 - May 28
Marram
Premium bedding, down comforters, minibar, in-room safe
Montauk Yacht Club
4.0 star property
8.4 out of 10, Very Good, (950)
"This place was redone so beautifully! The staff was incredible. Everything was so clean! We can’t wait to go back! We loved that it was even per friendly! Tim from the concierge was the most genuine person, leaving my kids a hand written note that they will never forget. Can’t say enough great things about this place! We stay in Montauk every year, this stay easily was my favorite one yet! Even the American girl dolls we brought were treated like royalty by the pool!"
The price is $379
$504 total
includes taxes & fees
May 27 - May 28
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 $695
$797 total
includes taxes & fees
Jun 4 - Jun 5
Topping Rose House
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 $315
$451 total
includes taxes & fees
May 27 - May 28
Hero Beach Club
Exterior
Journey East Hampton
4.0 star property
8.8 out of 10, Excellent, (89)
"Loved the room, bed was comfortable, shower was lovely. Cindy gave great suggestions on where to go."
The price is $293
$367 total
includes taxes & fees
May 27 - May 28
Journey East Hampton
Breakfast and dinner served
Copper Beech Inn
4.0 star property
8.6 out of 10, Excellent, (455)
"The room was large, very nice and clean. "
The price is $209
$240 total
includes taxes & fees
May 28 - May 29
Copper Beech Inn
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 27 - May 28
The Roundtree, Amagansett
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 $518
$719 total
includes taxes & fees
May 28 - May 29
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, (27)
"Absolutely the nicest hotel in the area. "
The price is $550
$659 total
includes taxes & fees
May 27 - May 28
Canoe Place Inn and Cottages
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 Maidstone
Aerial view
East Hampton Art House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (54)
"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 27 - May 28
East Hampton Art House Bed & Breakfast
Indoor pool, seasonal outdoor pool, sun loungers
The Baker House 1650
4.5 star property
9.4 out of 10, Exceptional, (33)
"Absolutely best place to stay in East Hampton! Charming B&B with incredible staff. "
The price is $700
$799 total
includes taxes & fees
May 29 - May 30
The Baker House 1650
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 $390
$553 total
includes taxes & fees
May 27 - May 28
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

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Shelter Island.
Vine & Sand

Vine & Sand

47100 New York 25, Southold, NY
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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.

Shelter Island Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Shelter Island, New York are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Shelter Island 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Shelter Island. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Shelter Island, New York, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Shelter Island hotels offer everything your heart desires.

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 $475

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.

Recent reviews of Shelter Island hotels
Expedia verified reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

5/5 Excellent
"Great time beautiful property"
A verified traveler stayed at Gurney's Montauk Resort & Seawater Spa
Posted 4 days ago
Gurney's Montauk Resort & Seawater Spa
Sound View Greenport

Sound View Greenport

5/5 Excellent
"Beautiful location. Staff was friendly and helpful. Dining was delicious. Rooms were renovated and spacious "
A verified traveler stayed at Sound View Greenport
Posted 3 weeks ago
Sound View Greenport