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Independent in Shelter Island

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

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Featured Shelter Island Independent

Montauk Manor
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
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 ...
Montauk Manor
Saybrook Point Resort & Marina
Saybrook Point Resort & Marina
3.5 out of 5
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
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 ...
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
Fully refundableReserve now, pay when you stay
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 ...
Water's Edge Resort & Spa
Sound View Greenport
Sound View Greenport
4 out of 5
58775 County Rd 48, Greenport, NY
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 ...
Sound View Greenport
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
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. ...
Pier Blue Inn Old Saybrook - Essex
The Harbor Front Inn
The Harbor Front Inn
3.5 out of 5
209 Front St, Greenport, NY
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 ...
The Harbor Front Inn
Gurney's Montauk Resort & Seawater Spa
Gurney's Montauk Resort & Seawater Spa
4 out of 5
290 Old Montauk Highway, Montauk, NY
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. ...
Gurney's Montauk Resort & Seawater Spa
Baron's Cove
Baron's Cove
4 out of 5
31 West Water Street, Sag Harbor, NY
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 ...
Baron's Cove
The Sagaponack
The Sagaponack
3 out of 5
3720 Montauk Hwy, Wainscott, NY
Stay at this 3-star B&B in Wainscott. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
The Sagaponack
Montauk Oceanside Suites
Montauk Oceanside Suites
3 out of 5
115 South Emerson Avenue, Montauk, NY
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 ...
Montauk Oceanside Suites
The Atlantic Hotel
The Atlantic Hotel
2.5 out of 5
1655 County Road 39, Southampton, NY
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 ...
The Atlantic Hotel
Journey East Hampton
Journey East Hampton
4 out of 5
490 Pantigo Road, East Hampton, NY
Stay at this 4-star hotel in East Hampton. Enjoy free breakfast, an outdoor pool, and free bicycles on site. Popular attractions East Hampton Historical Society ...
Journey East Hampton
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.

Independent hotels in Shelter Island

You’ve already taken the guesswork out of your next vacation. You know you want a Independent hotel in Shelter Island. What can you say? You like their style, they’re in a good part of Shelter Island, and they never let you down. New bar in town? You’re the first one to check it out. Spiciest item on the menu? You can take the heat. But even the best gamblers hedge their bets. No matter how crazy good your trip is, you want something familiar waiting for you at the end of the day.

All in a name

We all have favorites. There’s nothing wrong with knowing what you like. You like to stay at Independent near , Shelter Island to do the tourist thing (because sometimes it is fun) and then hit up the places that aren’t on the map. And no matter what fun you get into, you have Independent hotels with their comfy beds and thoughtful amenities waiting to tuck you in.

As you like it

Have a price you want to stick to, so you can paint the town red? Maybe, it’s all about the hotel features. Who couldn’t use a hot tub? Pick your pleasure by:

  • Hotwire Hot Rate: Grab the Independent hotel in Shelter Island at an absolute steal. After you book it, we’ll tell you the hotel name. You might nab that 4-star hotel for a 2-star price.
  • Price: How low can we go? Quite low in fact. Check out our prices per night, starting at $114.
  • Amenities: Grab a cocktail at the lounge and maybe wander upstairs to the rooftop terrace—all the stuff that makes a great vacay.

You’ve already done the hard part—figuring out where you want to stay. Now it’s time to use the money you saved to let the real fun begin. Underground shows? Off-beat attractions? Rooftop escapes? The choice is yours. The only thing wonderfully predictable about this trip is the Independent room you’ll be staying in.