Search for Cheap Deals on
Hotels in Shelter Island

Check Last Minute Shelter Island Hotel Deals

Tonight Jan 30 - Jan 31This weekend Jan 30 - Feb 1

Choose from 4681 Shelter Island Hotel Deals

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
Book a stay at this beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Popular attractions Hither Woods Preserve and Hither ...
8.2/10 Very Good! (719 reviews)
Staying at Gurney's after their many renovations was surprising !! The rooms don't look outdated anymore including the Spa / Pool area - for the price you're paying per night, I appreciated the face lift. Oceanviews from any angle of this hotel site will always be incredible !

Reviewed on Jan 12, 2026

Gurney's Montauk Resort & Seawater Spa
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
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. ...
7.8/10 Good! (1,000 reviews)
I have stayed here a number of times, and each time the room has been spotless and smells fresh. The staff is very friendly and always offers to help in some way, whether it's to get the snow off my car or provide bottled water. I will be staying here again!

Reviewed on Jan 23, 2026

Pier Blue Inn Old Saybrook - Essex
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue Montauk NY
  • 1 hour drive from Gardiner's Bay Country Club
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, a beach locale, and parking (surcharge). Popular attractions South Edison Beach and Kirk Park Beach ...
9.2/10 Wonderful! (188 reviews)
Great view of sunrise and sunset

Reviewed on Jan 19, 2026

Montauk Blue Hotel
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
  • 1 hour drive from Gardiner's Bay Country Club
Stay at this aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,287 reviews)
Everyone was perfect for our stay at the Montauk Manor!!! The lobby is beautiful and clean. The staff was friendly and very welcoming. We enjoyed massages with Amy, which I highly recommend. Breakfast was delicious at Monte’s (restaurant in the lobby). We loved our room it was immaculate and had ...

Reviewed on Jan 26, 2026

Montauk Manor
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
Book a stay at this 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! (608 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...

Reviewed on Jan 10, 2026

Sound View Greenport
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
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,003 reviews)
Great room and staff

Reviewed on Jan 14, 2026

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
Book a stay at this 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! (1,000 reviews)
Tamara, who checked us in, made a great first impression. She was friendly, helpful, and very accommodating.

Reviewed on Jan 28, 2026

Hyatt Place Long Island East End
Offshore Montauk

Offshore Montauk

2 out of 5
71 S Emerson Ave Montauk NY
  • 1 hour drive from Gardiner's Bay Country Club
Stay at this hotel in Montauk. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Kirk Park Beach and South Edison Beach are located ...
9.4/10 Exceptional! (97 reviews)
Clean, excellent service, great amenities, walking distance to the strip. Great value. Only thing was bathroom area was cold as air was seeping in. We stayed during the winter.

Reviewed on Jan 25, 2026

Offshore Montauk
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
Book a stay at this business-friendly hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (563 reviews)
The staff was wonderful and the room and views fantastic.

Reviewed on Jan 12, 2026

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
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 ...
7.6/10 Good! (1,000 reviews)
From the front desk to the rest of the staff, everyone was very friendly but also very professional and very helpful. I called the front desk about 5 straight times to ask questions I was waiting for the receptionist to e upset ,to my surprise she was laughing it up with me. That alone made my stay ...

Reviewed on Jan 21, 2026

Quality Inn Old Saybrook - Westbrook
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
Book a stay at this 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)
All was good at the hotel. No complaints

Reviewed on Jan 19, 2026

Saybrook Point Resort & Marina
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
  • 39 min drive from Gardiner's Bay Country Club
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
7/10 Good! (978 reviews)
Staff was very friendly room was clean and comfortable

Reviewed on Jan 11, 2026

The Atlantic Hotel
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 4,681 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 $91. 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 $91.

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 $91.

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.