Photo by tom owens

Shelter Island 4 Stars Hotels

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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

4.0 star property
8.6 out of 10, Excellent, (1009)
"Wonderful hotel and location "
Montauk Yacht Club

Sound View Greenport

4.0 star property
8.4 out of 10, Very Good, (571)
"Loved everything about my stay at the Sound view !! "
The price is NT$8,206
NT$10,846 total
includes taxes & fees
Sep 22 - Sep 23
Sound View Greenport

Gurney's Montauk Resort & Seawater Spa

4.0 star property
8.2 out of 10, Very Good, (667)
"Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay. "
The price is NT$14,086
NT$19,225 total
includes taxes & fees
Oct 1 - Oct 2
Gurney's Montauk Resort & Seawater Spa

Marram

4.0 star property
8.8 out of 10, Excellent, (224)
"Food was amazing, bed was so comfy and clean, overall 10/10"
The price is NT$6,694
NT$10,394 total
includes taxes & fees
Oct 13 - Oct 14
Marram

Baron's Cove

4.0 star property
9.0 out of 10, Wonderful, (284)
"Great location Rooms are very small but still amazing "
The price is NT$27,018
NT$33,955 total
includes taxes & fees
Sep 20 - Sep 21
Baron's Cove

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (77)
"Shelter Island is definitely a gem"
The Pridwin Hotel

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! "
The price is NT$9,571
NT$12,028 total
includes taxes & fees
Sep 25 - Sep 26
Journey East Hampton

Hero Beach Club

4.0 star property
9.0 out of 10, Wonderful, (190)
"Great service and location. Definitely will be back."
The price is NT$5,414
NT$7,732 total
includes taxes & fees
Oct 19 - Oct 20
Hero Beach Club

Silver Sands Motel & Beach Bungalows

4.0 star property
9.8 out of 10, Exceptional, (126)
"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

4.0 star property
9.4 out of 10, Exceptional, (318)
"the staff was exceptional and our dinner was very good"
The price is NT$10,958
NT$12,601 total
includes taxes & fees
Sep 29 - Sep 30
Madison Beach Hotel

Canoe Place Inn and Cottages

4.0 star property
9.8 out of 10, Exceptional, (56)
"Amazing property. Really enjoyed our stay."
Canoe Place Inn and Cottages

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (133)
"Great location and very comfortable "
The price is NT$16,092
NT$18,490 total
includes taxes & fees
Oct 6 - Oct 7
Topping Rose House

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 NT$8,384
NT$9,642 total
includes taxes & fees
Sep 22 - Sep 23
Copper Beech Inn

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (89)
"The Roundtree was one of the most peaceful hotels we’ve ever stayed in. I highly recommend for a romantic getaway. "
The price is NT$17,880
NT$21,449 total
includes taxes & fees
Oct 1 - Oct 2
The Roundtree, Amagansett

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 NT$9,766
NT$13,351 total
includes taxes & fees
Oct 6 - Oct 7
The 1770 House Restaurant & Inn

The Maidstone

4.0 star property
8.0 out of 10, Very Good, (147)
"We had a wonderful stay "
The Maidstone

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 NT$8,169
NT$9,068 total
includes taxes & fees
Oct 2 - Oct 3
James Pharmacy Bed & Breakfast

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 NT$17,147
NT$19,590 total
includes taxes & fees
Sep 29 - Sep 30
East Hampton Art House Bed & Breakfast

Canoe Place Waterfront Residences

4.0 star property
10.0 out of 10, Exceptional, (1)
Canoe Place Waterfront Residences

Offshore Residences

4.0 star property
The price is NT$15,912
NT$21,616 total
includes taxes & fees
Oct 20 - Oct 21
Offshore Residences
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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.

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.

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

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 NT$16,066

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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