Search for Cheap Deals onHotels in Shelter Island
Choose from 4678 Shelter Island Hotel Deals
Gurney's Montauk Resort & Seawater Spa
Everything was perfect. Staff, room, experience. Will definitely stay again.
Reviewed on Dec 14, 2025
Water's Edge Resort & Spa
Looks great
Reviewed on Dec 23, 2025
Montauk Blue Hotel
I always have a 5/5 stay at Montauk Blue.
Reviewed on Nov 19, 2025
Pier Blue Inn Old Saybrook - Essex
Its okay, some of the furniture didn't look in good shape. Bed was good, bathrooms were neat and good. I loved the rustic wood table. Also its high time we have smart TVs now. They are dirt cheap.
Reviewed on Dec 21, 2025
Offshore Montauk
Hotel was beautiful !!
Reviewed on Dec 22, 2025
The Bentley Hotel Southampton
Room was beautiful and spacious. Staff was courteous and on point.
Reviewed on Dec 22, 2025
Montauk Manor
Beautiful place as always, love the hot tub and sauna.
Reviewed on Dec 22, 2025
The Harbor Front Inn
Welcoming and kind staff! Nice breakfast, wasn’t too over the top. Room was spacious and view was lovely! The elevator wasn’t working so they waved the parking fee which was so nice considering we were on the first floor and didn’t need the elevator. Gave 4 starts because our fridge wasn’t working ...
Reviewed on Dec 10, 2025
Bayview Resort
Just right.
Reviewed on Nov 19, 2025
Sea Crest Resort
Lovely, clean 1 bedroom with spectacular view
Reviewed on Dec 13, 2025
Saybrook Point Resort & Marina
Amazing stay. Staff made it feel welcoming and cozy. Room was comfortable and charming. Looking forward to going back in the spring or summer to enjoy more of the outdoor amenities.
Reviewed on Dec 26, 2025
Sound View Greenport
Great room with amazing views! Staff was fantastic and the food was great too
Reviewed on Nov 28, 2025
Find cheap hotels in Shelter Island
You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Shelter Island hotel with Hotwire to complete your one-of-a-kind travel checklist.
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 4,678 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.
While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Shelter Island. No matter your reason for visiting Shelter Island, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.
Frequently Asked Questions About Shelter Island hotels
Where can I find the best last-minute travel deals?
If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Shelter Island for as low as $79.
How many hotels are there in Shelter Island?
With over 4,678 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.
- LaGuardia Airport Hotels
- Stewart Intl. Airport Hotels
- John F. Kennedy Intl. Airport Hotels
- Newark Liberty Intl. Airport Hotels
- Montauk Airport Hotels
- Brookhaven Calabro Airport Hotels
- Elizabeth Field Airport Hotels
- Groton - New London Airport Hotels
- Tweed - New Haven Regional Airport Hotels
- Westerly State Airport Hotels
- East Hampton Airport Hotels
- Francis S. Gabreski Airport Hotels
- Hotels near Gardiner's Bay Country Club
- Hotels near Mashomack Preserve
- Hotels near Shelter Island Historical Society
- Hotels near Shelter Island Whale's Tail
- Hotels near Shell Beach
- Hotels near Wades Beach
- Hotels near Havens House
- Hotels near Cooper's Beach
- Hotels near Ocean Beach Park
- Hotels near East Hampton Main Beach
- Hotels near Hammonasset Beach State Park
- Hotels near Wolffer Estates Vineyard
- Hotels near Essex Steam Train
- Hotels near Shinnecock Hills Golf Course
- Hotels near Hither Hills State Park
- Hotels near Westbrook Town Beach
- Hotels near Connecticut River
- Hotels near Orient Point County Park
- Hotels near Ditch Plains Beach
- Hotels near Raphael Winery
- Montauk Hotels
- Long Island Hotels
- Westbrook Hotels
- Hamptons Hotels
- Riverhead Hotels
- East Hampton Hotels
- Greenport Hotels
- Old Saybrook Hotels
- Southampton Hotels
- East Quogue Hotels
- New London Hotels
- Noyack Hotels
- Sag Harbor Hotels
- Hampton Bays Hotels
- Madison Hotels
- Old Lyme Hotels
- Southold Hotels
- Niantic Hotels
- Amagansett Hotels
- Waterford Hotels
