Search for Cheap Deals on
Hotels in Shelter Island

Photo by tom owens

Choose from 4787 Shelter Island Hotel Deals

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
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)
"Beautiful property with very friendly staff. We had a dog with us and they brought a bed and bowls for him to our room."

Reviewed on May 18, 2025

Montauk Yacht Club
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, free parking, and a beach locale. Popular attractions Montauk Point and South Edison Beach are located ...
9.2/10 Wonderful! (61 reviews)
"Walking distance to everything in the area. Right on the beach with a nice view and very friendly staff!"

Reviewed on May 20, 2025

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 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! (1,188 reviews)
"Nice historical building. Rooms well appointed and a beautiful view."

Reviewed on May 25, 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
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! (630 reviews)
"I liked everything except the valet parking because the guys don't take care of the cars. They left the light on and my car ran out of battery. Plus, they hit the handbrake and moved the car like that and ruined my traction."

Reviewed on May 12, 2025

Gurney's Montauk Resort & Seawater Spa
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! (854 reviews)
"Great little property! Very nice!"

Reviewed on May 22, 2025

The Atlantic Hotel
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
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 ,great for mtgs"

Reviewed on May 25, 2025

Water's Edge Resort & 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. ...
7.6/10 Good! (960 reviews)
Little gem of a motel in Old Saybrook.
"Very good basic hotel in a nice town. Room was clean and had everything you would need for a traveler. I had a late arrival due to traffic and the check in clerk contacted me to ask about my status. He was very nice and helpful. Motel offers no food service, but there is a very nice breakfast spot ..."

Reviewed on May 20, 2025

Pier Blue Inn Old Saybrook - Essex
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
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! (243 reviews)
"Great place to stay in Sag Harbor. Walk to town, and easy drives to all Hamptons. Will return."

Reviewed on May 19, 2025

Baron's Cove
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
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! (1,000 reviews)
"Perfect hotel for a short stay."

Reviewed on May 16, 2025

Hyatt Place Long Island East End
Sag Harbor Inn
Sag Harbor Inn
3.5 out of 5
45 West Water Street, Sag Harbor, NY
  • 16 min drive from Gardiner's Bay Country Club
Stay at this 3.5-star business-friendly hotel in Sag Harbor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (521 reviews)
"Comfortable room overlooking the harbor. Breakfast was basic but good. Walkable to the main area of town with restaurants and shops. Was a nice stay with friendly staff. The only change I would suggest is the signage and door access. There was one sign to the pool which led down into a stairwell ..."

Reviewed on May 18, 2025

Sag Harbor Inn
Beachcomber Resort at Montauk
Beachcomber Resort at Montauk
3 out of 5
727 Old Montauk Highway, Montauk, NY
  • 1 hour drive from Gardiner's Bay Country Club
Stay at this 3-star beach hotel in Montauk. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (519 reviews)
"It is the perfect location...across street from ocean and walkable to town."

Reviewed on May 22, 2025

Beachcomber Resort at Montauk
Silver Sands Motel & Beach Bungalows
Silver Sands Motel & Beach Bungalows
4 out of 5
1400 Silvermere Rd, Greenport, NY
  • 8 min drive from Gardiner's Bay Country Club
Stay at this 4-star beach hotel in Greenport. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.6/10 Exceptional! (88 reviews)
"I found the Silver Sands facility an attractive place. The bungalow where we stayed was very well decorated. Room service was A+. The weather was not the best one but we managed to enjoy ourselves. My only suggestion is to make pathways in concrete so that it is easier to move the luggage from the ..."

Reviewed on May 25, 2025

Silver Sands Motel & Beach Bungalows
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 4,787 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 4,787 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.