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Hotels in Shelter Island

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Choose from 4795 Shelter Island Hotel Deals

Marram
Marram
4 out of 5
21 Oceanview Terrace, Montauk, NY
  • 1 hour drive from Gardiner's Bay Country Club
Stay at this 4-star beach hotel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Montauk Point Lighthouse and Montauk Point ...
8.6/10 Excellent! (180 reviews)
"We loved our stay at Marram! The property is a little slice of beach magic. The location was absolutely perfect, and the private beach was exactly what we were hoping for. Tranquil and beautiful, they have effortlessly blended luxury into the unpretentious surf town vibes that Montauk is known for. ..."

Reviewed on Jul 10, 2025

Marram
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! (1,007 reviews)
Excellent Place to Stay!!!...5 Stars & More!!
"We stayed 5 days! Customer service was great ;) Housekeeping was great, the cafe in the morning was excellent! Lounge area if you wanted to go out in the evening they had Pool, Darts, & Karaoke If you didn't want to go to the Beach, they had a Pool/Gym Right near the Highway & Route 1 We had a wonderful ..."

Reviewed on Jul 10, 2025

Quality Inn Old Saybrook - Westbrook
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 Montauk Point Lighthouse and Montauk ...
9.2/10 Wonderful! (95 reviews)
Ocean front room
"Stayed in an ocean front room. Everything about this hotel was nice except the room didn’t seem very clean upon arrival. Hair in the shower, the bathroom counter top didn’t look like it was wiped down, finger prints on the mirror, dirt stains on the skirt of the bed. Only other complaint is the upkeep ..."

Reviewed on Jul 9, 2025

Montauk Blue Hotel
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! (1,006 reviews)
"Excellent"

Reviewed on Jul 10, 2025

Montauk Yacht Club
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! (642 reviews)
"We were able to check in early. Nice staff"

Reviewed on Jun 23, 2025

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. ...
7.6/10 Good! (990 reviews)
"The roadside in exceeded my expectations in all areas"

Reviewed on Jul 9, 2025

Pier Blue Inn Old Saybrook - Essex
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 Montauk Point Lighthouse and Montauk Point are located ...
9/10 Wonderful! (15 reviews)
Excellent
"Beautiful hotel! All sharp and excellent condition - I loved the bed - sheets etc!"

Reviewed on Jul 9, 2025

Offshore Montauk
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
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! (1,003 reviews)
"Fantastic!! Loved staying at this luxurious hotel"

Reviewed on Jul 8, 2025

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! (872 reviews)
"Lovely location that had everything you could ask for- just way too close to the highway. Nearly impossible to exit and enter the parking lot; someone should look into petitioning for a traffic light there. Other than that we had a great time!"

Reviewed on Jul 12, 2025

The Atlantic Hotel
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! (264 reviews)
"Really beautiful and clean property that is very convenient and great amenities."

Reviewed on Jun 27, 2025

Baron's Cove
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
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! (536 reviews)
Excellent views
"Nice quiet place with excellent views to spend the night"

Reviewed on Jul 13, 2025

Sound View Greenport
The Bentley Hotel Southampton
The Bentley Hotel Southampton
2 out of 5
161 Hills Station Rd, Southampton, NY
  • 40 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 and the clean rooms in our reviews. ...
9.4/10 Exceptional! (279 reviews)
"Great little gem in Southampton"

Reviewed on Jul 4, 2025

The Bentley Hotel Southampton
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 4,795 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 $102. 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 $102.

How many hotels are there in Shelter Island?

With over 4,795 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 $102.

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.