Photo by tom owens

Find 4 Star Hotels in Shelter Island, NY from ￥40,801

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Check availability on Shelter Island 4 Star Hotels

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

Montauk Yacht Club
Relax by the pool with a clear view of the water, surrounded by lounge chairs and umbrellas.

Montauk Yacht Club

4.0 star property
8.6 out of 10, Excellent, (1005)
"Wonderful place to visit "
Montauk Yacht Club
Gurney's Montauk Resort & Seawater Spa
Couples can exchange vows on a picturesque deck overlooking the water, surrounded by elegant archways and comfortable seating.

Gurney's Montauk Resort & Seawater Spa

4.0 star property
8.2 out of 10, Very Good, (642)
"Gurneys Inn was a beautiful place to stay. The staff extremely attentive and friendly!"
The price is ￥119,604
￥163,242 total
includes taxes & fees
Jul 30 - Jul 31
Gurney's Montauk Resort & Seawater Spa
Baron's Cove
Enjoy the charming balcony with potted plants and a gabled roof.

Baron's Cove

4.0 star property
9.0 out of 10, Wonderful, (261)
"Great location in the heart of town Walk to everything Amazing breakfast too "
The price is ￥64,199
￥80,682 total
includes taxes & fees
Jul 27 - Jul 28
Baron's Cove
Marram
Relax by the ocean with a clear view from this poolside area, featuring lounge chairs and umbrellas for shade.

Marram

4.0 star property
8.6 out of 10, Excellent, (178)
"Excellent beach location! "
The price is ￥69,132
￥106,618 total
includes taxes & fees
Jul 16 - Jul 17
Marram
Silver Sands Motel & Beach Bungalows
Enjoy meals with a scenic view of the water from this outdoor dining area.

Silver Sands Motel & Beach Bungalows

4.0 star property
9.8 out of 10, Exceptional, (103)
"Wonderful location and hotel "
Silver Sands Motel & Beach Bungalows
Sound View Greenport
Relax by the serene pool surrounded by lounge chairs and umbrellas.

Sound View Greenport

4.0 star property
8.4 out of 10, Very Good, (532)
"We had an overall great stay and will be back. Especially loved nights out on the beach!"
The price is ￥59,069
￥75,006 total
includes taxes & fees
Jul 23 - Jul 24
Sound View Greenport
Canoe Place Inn and Cottages
Relax in a serene outdoor setting with a covered patio, decorative water feature, and traditional architecture.

Canoe Place Inn and Cottages

4.0 star property
10.0 out of 10, Exceptional, (45)
"Wonderful stay! "
Canoe Place Inn and Cottages
Journey East Hampton
Stylish building with a brick and white exterior, featuring large windows and a covered outdoor area with a deck and potted plants.

Journey East Hampton

4.0 star property
9.0 out of 10, Wonderful, (139)
"We had a good stay at The Journey. Can’t wait to come back! "
Journey East Hampton
The Pridwin Hotel
Relax by the calm pool, surrounded by comfortable sun loungers and shaded areas.

The Pridwin Hotel

4.0 star property
9.4 out of 10, Exceptional, (63)
"Lovely hotel/ resort. Look forward to going again!"
The Pridwin Hotel
Hero Beach Club
Relax in a spacious room with a large bed, separate seating area, and a large window offering a view of the outdoors.

Hero Beach Club

4.0 star property
9.0 out of 10, Wonderful, (173)
"Great location. Very friendly staff. Definitely will be back. "
The price is ￥58,050
￥80,557 total
includes taxes & fees
Jul 13 - Jul 14
Hero Beach Club
Madison Beach Hotel
Enjoy ocean views and beach access from our waterfront rooms and suites.

Madison Beach Hotel

4.0 star property
9.4 out of 10, Exceptional, (299)
"Great stay!! "
The price is ￥87,954
￥101,147 total
includes taxes & fees
Jul 13 - Jul 14
Madison Beach Hotel
Offshore Montauk
Suite, 2 Queen Beds, Kitchenette, Ocean View | 1 bedroom, pillowtop beds, blackout drapes, free WiFi

Offshore Montauk

2.0 star property
9.2 out of 10, Wonderful, (15)
"Great stay"
The price is ￥72,257
￥99,261 total
includes taxes & fees
Jul 24 - Jul 25
Offshore Montauk
The Maidstone
Stunning traditional building with a beautifully lit entrance and lush surroundings.

The Maidstone

4.0 star property
8.0 out of 10, Very Good, (139)
"The details in this beautiful spot is what makes it so special and magical. "
The price is ￥102,466
￥117,068 total
includes taxes & fees
Jul 15 - Jul 16
The Maidstone
The Roundtree, Amagansett
Enjoy a leisurely ride along the beach, where the ocean meets the shore.

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 ￥189,381
￥227,187 total
includes taxes & fees
Jul 14 - Jul 15
The Roundtree, Amagansett
Copper Beech Inn
Enjoy dining in this spacious room with a high ceiling and glass roof, featuring a dining area with wooden tables and chairs.

Copper Beech Inn

4.0 star property
8.6 out of 10, Excellent, (498)
"Tired, expensive needs update"
The price is ￥40,801
￥46,921 total
includes taxes & fees
Jul 21 - Jul 22
Copper Beech Inn
The 1770 House Restaurant & Inn
Relax in a cozy living room with a comfortable sofa set, bookshelves, and ambient lighting.

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (155)
"The staff was incredibly genuine and the property felt intimate and comfortable."
The price is ￥84,289
￥115,230 total
includes taxes & fees
Jul 13 - Jul 14
The 1770 House Restaurant & Inn
Topping Rose House
Enjoy a pool and outdoor dining area with lounge chairs and a clear view of the surrounding landscape.

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (133)
"Had an excellent stay at Topping Rose House! Can’t wait to be back soon!"
The price is ￥184,044
￥210,783 total
includes taxes & fees
Jul 16 - Jul 17
Topping Rose House
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
The price is ￥388,304
￥470,256 total
includes taxes & fees
Aug 4 - Aug 5
Canoe Place Waterfront Residences
Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard
Enjoy cooking in this well-lit kitchen with a range hood, island, and ample seating area.

Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard

4.0 star property
10.0 out of 10, Exceptional, (3)
"Our short trip to sag harbor was planned very last minute. Raymond was more the than happy to accommodate and left us a really nice goody bag to boot !! The house was newly renovated with all the expected amenities. Lots of sleeping quarters yet felt cozy. From the pool and pool house, the outdoor kitchen, “driving range” and gym there was something for everyone !! Raymond was a gracious host!"
Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard
434 on Main
Enjoy a peaceful view of the outdoors from this room's large window, which also illuminates the space.

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
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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 ￥145,509 per night from Jul 27 to Jul 28
￥145,509
￥182,867 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (69 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

Escape to Shelter Island! Enjoy its island views, natural setting, and beaches.

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

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 ￥145,509

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.