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Hotels in Shelter Island

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Choose from 4681 Shelter Island Hotel Deals

Montauk Manor
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
  • 1 hour drive from Gardiner's Bay Country Club
The price is $169 per night from Mar 17 to Mar 18
$169
includes taxes & fees
Mar 17 - Mar 18
Stay at this 3.5-star aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,135 reviews)
weekend getaway
"perfect overnight getaway . suite and indoor pool was very nice and spotless. suite was like brand new inside with everything you could think of . staff was really friendly and helpful. restaurant had very good food thought portions could of been more generous but was very good . bar was ok but i ..."

Reviewed on Mar 9, 2025

Montauk Manor
Gurney's Montauk Resort & Seawater Spa
Gurney's Montauk Resort & Seawater Spa
4 out of 5
290 Old Montauk Highway, Montauk, NY
  • 56 min drive from Gardiner's Bay Country Club
The price is $525 per night from Mar 17 to Mar 18
$525
includes taxes & fees
Mar 17 - Mar 18
Stay at this 4-star beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Our guests praise the room service in our reviews. ...
8.2/10 Very Good! (613 reviews)
"It’s under construction so it’s not as nice as I typically would be. I wishes we had been warned . Although the staff is friendly and helpful"

Reviewed on Feb 20, 2025

Gurney's Montauk Resort & Seawater Spa
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 out of 5
1525 Boston Post Road, Westbrook, CT
  • 36 min drive from Gardiner's Bay Country Club
The price is $235 per night from Mar 16 to Mar 17
$235
includes taxes & fees
Mar 16 - Mar 17
Stay at this 3.5-star beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
8.6/10 Excellent! (1,001 reviews)
"Lovely property .... The dinner was great . Room service was very convenient and fast . The spa was wonderful Justine was amazing with the massage I felt so relaxed after. Our pedicures the next day were equally amazing, my feet are so soft and clean my polish is neat. I will definitely be back for ..."

Reviewed on Mar 10, 2025

Water's Edge Resort & Spa
Hyatt Place Long Island East End
Hyatt Place Long Island East End
3 out of 5
451 East Main Street, Riverhead, NY
  • 1 hour drive from Gardiner's Bay Country Club
The price is $118 per night from Mar 30 to Mar 31
$118
includes taxes & fees
Mar 30 - Mar 31
Stay at this 3-star business-friendly hotel in Riverhead. Enjoy free WiFi, free parking, and a marina. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,003 reviews)
Weekend getaway
"This hotel was top notch from top to bottom. Room was clean and our bed was very comfortable. Service was also excellent. A+++++"

Reviewed on Mar 9, 2025

Hyatt Place Long Island East End
Baron's Cove
Baron's Cove
4 out of 5
31 West Water Street, Sag Harbor, NY
  • 16 min drive from Gardiner's Bay Country Club
The price is $240 per night from Mar 18 to Mar 19
$240
includes taxes & fees
Mar 18 - Mar 19
Stay at this 4-star hotel in Sag Harbor. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (214 reviews)
Iconic Hotel in Iconic location
"Thoroughly enjoyed my stay at Baron's Cove. I stayed late February so the pool was closed, but this was expected. It's a motel style hotel where your door opens to the outside, but given the location of the hotel i felt perfectly safe. The Staff were fantastic, and always helpful. The breakfast was ..."

Reviewed on Feb 28, 2025

Baron's Cove
Saybrook Point Resort & Marina
Saybrook Point Resort & Marina
3.5 out of 5
2 Bridge St, Old Saybrook, CT
  • 32 min drive from Gardiner's Bay Country Club
The price is $329 per night from Mar 17 to Mar 18
$329
includes taxes & fees
Mar 17 - Mar 18
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
9.4/10 Exceptional! (1,000 reviews)
"Great location and friendly staff"

Reviewed on Mar 9, 2025

Saybrook Point Resort & Marina
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
  • 35 min drive from Gardiner's Bay Country Club
The price is $79 per night from Mar 24 to Mar 25
$79
includes taxes & fees
Mar 24 - Mar 25
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.6/10 Good! (928 reviews)
"Had a great experience at this hotel. It was very clean and convenient. Would stay here again in a heartbeat."

Reviewed on Feb 28, 2025

Pier Blue Inn Old Saybrook - Essex
Montauk Oceanside Suites
Montauk Oceanside Suites
3 out of 5
115 South Emerson Avenue, Montauk, NY
  • 1 hour drive from Gardiner's Bay Country Club
The price is $166 per night from Mar 14 to Mar 15
$166
includes taxes & fees
Mar 14 - Mar 15
Stay at this 3-star aparthotel in Montauk. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Montauk Point and South Edison Beach are ...
8.4/10 Very Good! (365 reviews)
"Had a great stay here . Staff was friendly and check in and out was a breeze . Was very clean and comfortable. Only complaint was I couldn’t get a hot shower . Otherwise place is excellent. Shops , restaurants and bars are all a short walk ."

Reviewed on Mar 2, 2025

Montauk Oceanside Suites
Montauk Yacht Club
Montauk Yacht Club
4 out of 5
32 Star Island Rd, Montauk, NY
  • 1 hour drive from Gardiner's Bay Country Club
The price is $361 per night from Apr 6 to Apr 7
$361
includes taxes & fees
Apr 6 - Apr 7
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the property condition ...
8.4/10 Very Good! (999 reviews)
"Great property, great service, quiet location"

Reviewed on Dec 23, 2024

Montauk Yacht Club
The Harbor Front Inn
The Harbor Front Inn
3.5 out of 5
209 Front St, Greenport, NY
  • 6 min drive from Gardiner's Bay Country Club
The price is $163 per night from Mar 27 to Mar 28
$163
includes taxes & fees
Mar 27 - Mar 28
Stay at this 3.5-star business-friendly hotel in Greenport. Enjoy free breakfast, an outdoor pool, and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (437 reviews)
"The two king beds room (#310) on the third floor had a bit of an unpleasant smell (stale carpet? dirty mop was used to wipe down the room?). We didn't report it and left the balcony door open to air it. But the second room (#113) was large, spacious and clean. We all had a comfortable night's sleep. ..."

Reviewed on Mar 5, 2025

The Harbor Front Inn
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
  • 38 min drive from Gardiner's Bay Country Club
The price is $92 per night from Apr 6 to Apr 7
$92
includes taxes & fees
Apr 6 - Apr 7
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.4/10 Good! (1,002 reviews)
"The breakfast coffee was sub par. The omelette was very good."

Reviewed on Mar 11, 2025

Quality Inn Old Saybrook - Westbrook
Sound View Greenport
Sound View Greenport
4 out of 5
58775 County Rd 48, Greenport, NY
  • 11 min drive from Gardiner's Bay Country Club
The price is $195 per night from Mar 17 to Mar 18
$195
includes taxes & fees
Mar 17 - Mar 18
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (509 reviews)
Out East Getaway
"Amazing location, great staff and very hotel boutique vibes."

Reviewed on Feb 25, 2025

Sound View Greenport
See all 4,681 properties in Shelter Island
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.

Find cheap hotels in Shelter Island

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For you, intrepid voyager, Hotwire has a large selection of the best hotels in Shelter Island.

Choosing the right hotel in New York has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Shelter Island’s 4,681 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $79. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Shelter Island hotel deals at the last minute.

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Frequently Asked Questions About Shelter Island hotels

Where can I find the best last-minute travel deals?

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How many hotels are there in Shelter Island?

With over 4,681 hotels in Shelter Island, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $79.

How to find cheap car rentals in Shelter Island?

Finding a cheap car rental deal in Shelter Island is as easy as scoring cheap hotels in Shelter Island. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.