Search for Cheap Deals on
Hotels in Shelter Island

Photo by tom owens

Check Last Minute Shelter Island Hotel Deals

Tonight Jan 11 - Jan 12Next weekend Jan 17 - Jan 19

Choose from 4675 Shelter Island Hotel Deals

Hyatt Place Long Island East End
Hyatt Place Long Island East End
3 out of 5
451 East Main Street, Riverhead, NY
  • 59 min drive from Shelter Island Historical Society
The price is $133 per night from Jan 12 to Jan 13
$133
includes taxes & fees
Jan 12 - Jan 13
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! (1,002 reviews)
"Just Great!"

Reviewed on Jan 8, 2025

Hyatt Place Long Island East End
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
  • 43 min drive from Shelter Island Historical Society
The price is $100 per night from Jan 19 to Jan 20
$100
includes taxes & fees
Jan 19 - Jan 20
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)
"Friendly and helpful staff and the breakfast was good. The only issue was one of the beds in our room (212) literally fell off the frame on one side when sat on.We were tired and had already settled in, so we didn’t request a new room and made it work."

Reviewed on Jan 8, 2025

Quality Inn Old Saybrook - Westbrook
Montauk Manor
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
  • 1 hour drive from Shelter Island Historical Society
The price is $169 per night from Jan 13 to Jan 14
$169
includes taxes & fees
Jan 13 - Jan 14
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! (1,090 reviews)
"Best old hotel on Long Island"

Reviewed on Jan 6, 2025

Montauk Manor
Saybrook Point Resort & Marina
Saybrook Point Resort & Marina
3.5 out of 5
2 Bridge St, Old Saybrook, CT
  • 37 min drive from Shelter Island Historical Society
The price is $364 per night from Jan 14 to Jan 15
$364
includes taxes & fees
Jan 14 - Jan 15
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)
Wonderful mother, daughter getaway
"This is a beautiful Inn that is beautifully maintained spacious, inviting and very comfortable. The spa is exceptional. My daughter and I felt that the massage and facial services we had were probably among the best we’ve experienced. We will definitely be back!"

Reviewed on Jan 4, 2025

Saybrook Point Resort & Marina
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 out of 5
1525 Boston Post Road, Westbrook, CT
  • 40 min drive from Shelter Island Historical Society
The price is $246 per night from Jan 12 to Jan 13
$246
includes taxes & fees
Jan 12 - Jan 13
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! (1,000 reviews)
"Well maintained, beautiful views."

Reviewed on Jan 6, 2025

Water's Edge Resort & Spa
Sound View Greenport
Sound View Greenport
4 out of 5
58775 County Rd 48, Greenport, NY
  • 12 min drive from Shelter Island Historical Society
The price is $216 per night from Jan 27 to Jan 28
$216
includes taxes & fees
Jan 27 - Jan 28
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! (496 reviews)
"The view from the room"

Reviewed on Jan 2, 2025

Sound View Greenport
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 Shelter Island Historical Society
The price is $436 per night from Feb 3 to Feb 4
$436
includes taxes & fees
Feb 3 - Feb 4
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! (609 reviews)
"Beautiful views. Great staff and amenities."

Reviewed on Nov 28, 2024

Gurney's Montauk Resort & Seawater Spa
Budget Host East End Hotel in Riverhead
Budget Host East End Hotel in Riverhead
2 out of 5
30 Lake Avenue, Riverhead, NY
  • 1 hour drive from Shelter Island Historical Society
The price is $118 per night from Jan 12 to Jan 13
$118
includes taxes & fees
Jan 12 - Jan 13
Stay at this motel in Riverhead. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. ...
6.4/10 (682 reviews)
great value
"great value"

Reviewed on Jan 2, 2025

Budget Host East End Hotel in Riverhead
The Harbor Front Inn
The Harbor Front Inn
3.5 out of 5
209 Front St, Greenport, NY
  • 8 min drive from Shelter Island Historical Society
The price is $194 per night from Jan 27 to Jan 28
$194
includes taxes & fees
Jan 27 - Jan 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! (428 reviews)
"Good"

Reviewed on Jan 4, 2025

The Harbor Front Inn
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
  • 39 min drive from Shelter Island Historical Society
The price is $114 per night from Jan 12 to Jan 13
$114
includes taxes & fees
Jan 12 - Jan 13
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! (902 reviews)
"A very nice hotel. The rooms were clean and comfortable."

Reviewed on Jan 1, 2025

Pier Blue Inn Old Saybrook - Essex
The Bentley Hotel Southampton
The Bentley Hotel Southampton
2 out of 5
161 Hills Station Rd, Southampton, NY
  • 36 min drive from Shelter Island Historical Society
The price is $183 per night from Jan 12 to Jan 13
$183
includes taxes & fees
Jan 12 - Jan 13
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9.4/10 Exceptional! (220 reviews)
"Had a great stay!"

Reviewed on Jan 1, 2025

The Bentley Hotel Southampton
Montauk Oceanside Suites
Montauk Oceanside Suites
3 out of 5
115 South Emerson Avenue, Montauk, NY
  • 1 hour drive from Shelter Island Historical Society
The price is $165 per night from Jan 12 to Jan 13
$165
includes taxes & fees
Jan 12 - Jan 13
Stay at this 3-star aparthotel in Montauk. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions South Edison Beach and Kirk Park Beach ...
8.4/10 Very Good! (351 reviews)
"Location, location..."

Reviewed on Dec 31, 2024

Montauk Oceanside Suites
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

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 4,675 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 $100. 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 $100.

How many hotels are there in Shelter Island?

With over 4,675 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 $100.

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.