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Independent in Shelter Island

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Featured Shelter Island Independent

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
Montauk Yacht Club
Montauk Yacht Club
4 out of 5
32 Star Island Rd, Montauk, NY
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 ...
Montauk Yacht Club
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, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the ...
The Harbor Front Inn
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
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
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 ...
Saybrook Point Resort & Marina
The Montauk Soundview
The Montauk Soundview
3 out of 5
6 Soundview Drive, Montauk, NY
Stay at this 3-star beach hotel in Montauk. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions ...
The Montauk Soundview
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
Montauk Blue Hotel
Montauk Blue Hotel
2 out of 5
108 South Emerson Avenue, Montauk, NY
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, free parking, and a beach locale. Popular attractions South Edison Beach and Kirk Park Beach are ...
Montauk Blue Hotel
Marram
Marram
4 out of 5
21 Oceanview Terrace, Montauk, NY
Stay at this 4-star beach hotel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions South Edison Beach and Kirk Park Beach are ...
Marram
The Pridwin Hotel
The Pridwin Hotel
4 out of 5
81 Shore Road, Shelter Island Heights, NY
Stay at this 4-star beach hotel in Shelter Island Heights. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
The Pridwin Hotel
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
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
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 $91.
  • 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.