Hotels in Shelter Island

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House on Chase Creek
House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (79 reviews)
The price is $104
$119 total
includes taxes & fees
Jan 15 - Jan 16
House on Chase Creek
The Harbor Front Inn
The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (562 reviews)
The price is $117
$162 total
includes taxes & fees
Jan 15 - Jan 16
The Harbor Front Inn
American Beech Hotel
American Beech Hotel
3.5 star property
Greenport
8.8 out of 10, Excellent, (195 reviews)
The price is $139
$199 total
includes taxes & fees
Jan 15 - Jan 16
American Beech Hotel
The Shoals Suites and Slips
The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (235 reviews)
The price is $169
$193 total
includes taxes & fees
Jan 22 - Jan 23
The Shoals Suites and Slips
Sound View Greenport
Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (606 reviews)
The price is $134
$182 total
includes taxes & fees
Jan 21 - Jan 22
Sound View Greenport
Silver Sands Motel & Beach Bungalows
Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (144 reviews)
The price is $330
$377 total
includes taxes & fees
Feb 6 - Feb 7
Silver Sands Motel & Beach Bungalows
Stirling House Bed & Breakfast
Stirling House Bed & Breakfast
3.0 star property
Greenport
9.8 out of 10, Exceptional, (24 reviews)
The price is $335
$383 total
includes taxes & fees
Jan 23 - Jan 24
Stirling House Bed & Breakfast
The Menhaden
The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (174 reviews)
The price is $242
$317 total
includes taxes & fees
Feb 12 - Feb 13
The Menhaden
The Rams Head Inn
The Rams Head Inn
4.0 star property
Shelter Island Heights
7.6 out of 10, Good, (18 reviews)
The price is $395
$451 total
includes taxes & fees
Jan 16 - Jan 17
The Rams Head Inn
Zey Hotel
Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (294 reviews)
The price is $225
$257 total
includes taxes & fees
Jan 15 - Jan 16
Zey Hotel
Vine & Sand
Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (13 reviews)
The price is $366
$419 total
includes taxes & fees
Jan 19 - Jan 20
Vine & Sand
The Sagaponack
The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (221 reviews)
The price is $169
$233 total
includes taxes & fees
Jan 23 - Jan 24
The Sagaponack
Topping Rose House
Topping Rose House
4.5 star property
Bridgehampton
9.2 out of 10, Wonderful, (139 reviews)
The price is $536
$615 total
includes taxes & fees
Jan 15 - Jan 16
Topping Rose House
Mill House Inn
Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (77 reviews)
The price is $250
$314 total
includes taxes & fees
Jan 18 - Jan 19
Mill House Inn
The 1770 House Restaurant & Inn
The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (162 reviews)
The price is $295
$403 total
includes taxes & fees
Jan 19 - Jan 20
The 1770 House Restaurant & Inn
The Maidstone
The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very Good, (150 reviews)
The price is $178
$203 total
includes taxes & fees
Jan 19 - Jan 20
The Maidstone
Bridgehampton Inn
Bridgehampton Inn
3.5 star property
Bridgehampton
9.4 out of 10, Exceptional, (220 reviews)
The price is $299
$342 total
includes taxes & fees
Jan 15 - Jan 16
Bridgehampton Inn
Journey East Hampton
Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (162 reviews)
The price is $185
$232 total
includes taxes & fees
Jan 18 - Jan 19
Journey East Hampton
Southampton Long Island Hotel
Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (206 reviews)
The price is $105
$125 total
includes taxes & fees
Jan 15 - Jan 16
Southampton Long Island Hotel
The Roundtree, Amagansett
The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (92 reviews)
The price is $594
$713 total
includes taxes & fees
Jan 15 - Jan 16
The Roundtree, Amagansett
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.

Top neighborhoods in Shelter Island

Silver Beach

Shelter Island's Silver Beach neighborhood offers attractions including Shell Beach.

Coecles Harbor

Shelter Island's Coecles Harbor neighborhood offers attractions including Menhadden Lane Beach.

Hay Beach

Shelter Island's Hay Beach neighborhood offers attractions including Menhadden Lane Beach.

Shorewood

Shelter Island's Shorewood neighborhood offers attractions including Wades Beach.

Top landmarks in Shelter Island

Learn more about Shelter Island

Shelter Island is well-known for its attractions such as Sunset Beach and Shelter Island Whale's Tail. The city has something for everyone including sights like Mashomack Preserve and Crescent Beach within a scenic setting.

Central Park summer

Check out reviews of Shelter Island hotels guests love

Frequently asked questions

What accommodations do travelers recommend in Shelter Island?
Can I book refundable hotels in Shelter Island?
If you're looking for the flexibility to change your travel plans to Shelter Island, most properties offer refundable* rates you can book. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Shelter Island if I want a vacation rental instead of a traditional hotel?
If you want to find a good alternative to a hotel, browse our selection of 89 vacation homes. You can also consider one of the 5 cottages for your trip.
What will the weather in Shelter Island be like during my trip?
The warmest months in Shelter Island are usually August and July with an average temp of 70°F. January and February are the chilliest months when the average temp is 38°F. The rainiest months are October and December.
Why should I book my Shelter Island accommodation with Hotels.com?
There are plenty of reasons to book your Shelter Island travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.