Shelter Island Hotels

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22 Aug - 23 Aug
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Top 10 trending Shelter Island hotels

Montauk Manor
Front of property – evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1240)
"I had the best time and highly recommend this hotel!"
The price is €308
includes taxes & fees
2 Sept - 3 Sept
Montauk Manor
Beachcomber Resort at Montauk
Seasonal outdoor pool

Beachcomber Resort at Montauk

3.0 star property
9.4 out of 10, Exceptional, (572)
"Clean, friendly and great location. "
Beachcomber Resort at Montauk
Saybrook Point Resort & Marina
Exterior

Saybrook Point Resort & Marina

3.5 star property
9.4 out of 10, Exceptional, (1002)
"The venue is great. "
The price is €369
includes taxes & fees
8 Sept - 9 Sept
Saybrook Point Resort & Marina
The Atlantic Hotel
Outdoor pool

The Atlantic Hotel

2.5 star property
7.2 out of 10, Good, (914)
"great stay "
The Atlantic Hotel
Marram
Seasonal outdoor pool, pool umbrellas, pool loungers

Marram

4.0 star property
8.8 out of 10, Excellent, (213)
"Food was amazing, bed was so comfy and clean, overall 10/10"
The price is €448
includes taxes & fees
15 Sept - 16 Sept
Marram
Ocean Surf Resort
View from property

Ocean Surf Resort

2.0 star property
8.4 out of 10, Very good, (191)
"Great location, amazing view, clean, friendly and helpful staff."
The price is €124
includes taxes & fees
15 Sept - 16 Sept
Ocean Surf Resort
Hampton Bays Hotel on Main
Deluxe Double Room, 1 King Bed, City View

Hampton Bays Hotel on Main

2.0 star property
6.6 out of 10, (52)
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
Hampton Bays Hotel on Main
Greenporter Hotel
Property grounds

Greenporter Hotel

2.0 star property
9.2 out of 10, Wonderful, (180)
"Close to town and pool was great!"
Greenporter Hotel
Gurney's Montauk Resort & Seawater Spa
Outdoor wedding area

Gurney's Montauk Resort & Seawater Spa

4.0 star property
8.2 out of 10, Very good, (658)
"Place is All Time! "
The price is €736
includes taxes & fees
22 Sept - 23 Sept
Gurney's Montauk Resort & Seawater Spa
Offshore Montauk
Outdoor pool

Offshore Montauk

2.0 star property
9.4 out of 10, Exceptional, (37)
"Great stay"
The price is €391
includes taxes & fees
4 Sept - 5 Sept
Offshore Montauk
The Preston House & Hotel
Front of property

The Preston House & Hotel

3.5 star property
9.8 out of 10, Exceptional, (357)
"I cannot wait to go back. I will make excuses to stay there again!"
The price is €310
includes taxes & fees
25 Aug - 26 Aug
The Preston House & Hotel
Pier Blue Inn Old Saybrook - Essex
Property grounds

Pier Blue Inn Old Saybrook - Essex

2.0 star property
7.8 out of 10, Good, (1006)
"Hotel was very clean, reasonable price, and convenient traveling"
The price is €79
includes taxes & fees
2 Sept - 3 Sept
Pier Blue Inn Old Saybrook - Essex
The Harbor Front Inn
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool loungers

The Harbor Front Inn

3.5 star property
8.8 out of 10, Excellent, (506)
"Great getaway! "
The price is €250
includes taxes & fees
21 Sept - 22 Sept
The Harbor Front Inn
The Montauk Soundview
Cottage, 2 Bedrooms (Waterfront)

The Montauk Soundview

3.0 star property
8.6 out of 10, Excellent, (301)
"The Soundview was the perfect location for our Montauk vacation."
The price is €237
includes taxes & fees
15 Sept - 16 Sept
The Montauk Soundview
Water's Edge Resort & Spa
Exterior

Water's Edge Resort & Spa

3.5 star property
8.8 out of 10, Excellent, (1006)
"Clean, comfortable stay. Beautiful resort! Would stay again! "
The price is €252
includes taxes & fees
15 Sept - 16 Sept
Water's Edge Resort & Spa
Montauk Yacht Club
Indoor pool, 2 outdoor pools

Montauk Yacht Club

4.0 star property
8.6 out of 10, Excellent, (1000)
"Luxurious, quiet, and a wonderful, indulgent place to restore."
Montauk Yacht Club
The Hampton Maid
Property grounds

The Hampton Maid

2.5 star property
9.0 out of 10, Wonderful, (634)
"Great place to stay"
The Hampton Maid
Zey Hotel
Exterior

Zey Hotel

3.5 star property
9.2 out of 10, Wonderful, (266)
"Great location and friendly staff "
Zey Hotel
Bayview Resort
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, free pool cabanas

Bayview Resort

2.5 star property
8.8 out of 10, Excellent, (427)
"Nice rooms and kind, helpful staff. Continental breakfast is a great perk!"
The price is €217
includes taxes & fees
15 Sept - 16 Sept
Bayview Resort
Sole East Resort
Seasonal outdoor pool

Sole East Resort

3.0 star property
7.8 out of 10, Good, (105)
"Great location Beautiful boutique style hotel Always a great stay"
The price is €336
includes taxes & fees
2 Sept - 3 Sept
Sole East Resort
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.
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Check out family-friendly hotels in Shelter Island

Work and Play Special! Extended Stay Discount
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (49)
The price is €1,268
includes taxes & fees
14 Sept - 15 Sept
Work and Play Special! Extended Stay Discount

Hotels with a pool in Shelter Island you'll enjoy

Work and Play Special! Extended Stay Discount
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (49)
The price is €1,268
includes taxes & fees
14 Sept - 15 Sept
Work and Play Special! Extended Stay Discount

These pet-friendly hotels in Shelter Island may fit your trip

Work and Play Special! Extended Stay Discount
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (49)
The price is €1,268
includes taxes & fees
14 Sept - 15 Sept
Work and Play Special! Extended Stay Discount
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.

Where to stay in Shelter Island

Find the best Shelter Island areas for the activities you enjoy most.

Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Sunset Beach and Crescent Beach.

Silver Beach

While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.

Coecles Harbor

While Coecles Harbor isn't home to many top sights, Shelter Island Whale's Tail and Gardiner's Bay Country Club are some notable places to visit nearby.

Hay Beach

When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.

Shorewood

While Shorewood may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach.

Near an Attraction

Shelter Island Whale's Tail

Shelter Island Whale's Tail

You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area.

See properties in Shelter Island Whale's Tail

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
Photo by tom owens
Open Photo by tom owens

Top Shelter Island Hotel Reviews

Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Walkable to the beach. Have to cross a highway which was not as wide or busy, so it was easy."
Srini 2-night trip
Posted 2 days ago
Beachcomber Resort at Montauk

Frequently asked questions

Where is the best place to stay in Shelter Island?

Located 21 mi (33.9 km) from the heart of Shelter Island, Marram is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Beachcomber Resort at Montauk and Montauk Yacht Club. See all available top hotels, or vacation rentals in Shelter Island.

What are some of the best holiday rentals that Shelter Island has to offer?

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres: This highly rated holiday home rental in Shelter Island is equipped with a BBQ, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities such as a stovetop and a microwave can make your holiday run smoothly. See all vacation rentals in Shelter Island.

If I need to cancel my hotel reservation in Shelter Island, will I receive a refund?

Yes! You'll find that most hotel bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If your reservation is non-refundable, you might be able to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Shelter Island.

What's the best dog-friendly accommodation option in Shelter Island?

Sunset Beach Hotel is a top hotel for people travelling with their pets, and offers a restaurant and free WiFi for its human guests. See more pet-friendly hotel accommodations in Shelter Island.

What's the best hotel to stay near the beach in Shelter Island?

Sunset Beach Hotel is a top beachfront hotel with free WiFi and free parking, and it's located on Sunset Beach . See more stays near the beach in Shelter Island.

What are some accommodation options with pools in Shelter Island?

Marram: Hotel, 6-minute walk from The Hamptons Beaches. Features free self parking, a seasonal outdoor pool and sunloungers. Beachcomber Resort at Montauk and Montauk Yacht Club are a couple of other choices that offer an on-site pool. View all hotels with pools in Shelter Island.

What's it like to stay in Shelter Island?

Visitors can enjoy all that Shelter Island has to offer, including the parks, beaches and museums. This city also attracts tourists with its scenic landscape. In Shelter Island, there are 94 hotels and other accommodation options to choose from. Find out more about Shelter Island.

What should I see while I'm in Shelter Island?

Natural beauty is on display at Sunset Beach, Crescent Beach and Wades Beach. A couple of additional sights to add to your itinerary are Shelter Island Whale's Tail and Gardiner's Bay Country Club. Take a look at what more there is to see and do in Expedia's Shelter Island guide.

What's the seasonal weather in Shelter Island?

The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Shelter Island is 1452 mm.