Find 5 Star Hotels in Shelter Island, NY from $251
Most hotels are fully refundable. Because flexibility matters.
Save 10% or more on over 100,000 hotels worldwide as a One Key member.
Search over 2.9 million properties and 550 airlines worldwide.
Check availability on Shelter Island 5 Star Hotels
Compare Shelter Island 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.
Vine & Sand
Mill House Inn
Casa Newmark Holiday home 7 BestStayz.1
Explore similar 4-star hotels
Gurney's Montauk Resort & Seawater Spa
Ready for an incredible adventure? Add further enjoyment on your next trip to Shelter Island by treating yourself to the best of the best when it comes to accommodation. It's an ideal fusion. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Shelter Island so popular in the last year. There's no reason to delay a getaway to Shelter Island any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Our 5-star hotels in Shelter Island are the perfect places to relax in during your next getaway. You deserve the great vacation you're dreaming about.
Get a Great Deal on 5-Star Hotels in Shelter Island
You'll have a fantastic time at one of these 5-star hotels. Spa treatments, delicious meals, and attentive guest service are all waiting for you. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. What kind of amenities will make your stay a wonderful one? A rejuvenating facial treatment to help your cares fall away? A concierge to help you suggest the next attraction to visit? Plush carpeting, lip-smacking main courses, and even spectacular views...these hotels will leave you amazed. Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs.
You won't sleep and order room service the entire time, though. We hear you. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Shelter Island are the perfect place to relax after an exciting day.
Make Your Escape
The results are in, and Shelter Island 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. It's time to indulge yourself. Opt for one of Expedia's Shelter Island 5-star hotels today and soothe yourself in luxe surroundings tomorrow.
Frequently asked questions
Shelter Island Hotels by Star Rating
Hotels in Shelter Island Neighborhoods
Stay near popular Shelter Island attractions
- Gardiner's Bay Country Club
- Shell Beach
- Mashomack Preserve
- Shelter Island Historical Society
- Shelter Island Whale's Tail
- Wades Beach
- Havens House
- Hammonasset Beach State Park
- Cooper's Beach
- Ocean Beach Park
- East Hampton Main Beach
- Wolffer Estates Vineyard
- Hither Hills State Park
- Rocky Neck State Park
- Essex Steam Train
- Orient Point County Park
- Clinton Crossing Premium Outlets
- Connecticut River
- Ditch Plains Beach
- 67 Steps Beach
More Hotel Options in Shelter Island
Explore more hotels
- The Harbor Front Inn
- Sound View Greenport
- Beachcomber Resort at Montauk
- Southampton Inn
- Water's Edge Resort & Spa
- Pier Blue Inn Old Saybrook - Essex
- Kenny's Tipperary Inn
- The Bentley Hotel Southampton
- Montauk Oceanside Suites
- The Shoals Suites and Slips
- Silver Sands
- Sea Crest Resort
- The Preston House & Hotel
- Baron's Cove
- Village Motel By OYO Clinton
- Breakers Montauk
- Madison Beach Hotel
- Shorewood Inn
- Marram
- The Surf Club