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Independent in Shelter Island

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
$521 nightly
The price is $595 total per night
$595 total
May 5 - May 6
Total with taxes and fees
18.43 mi from city center
Located in Montauk, Gurney's Montauk Resort & Seawater Spa is by the ocean, a 3-minute drive from Hither Hills State Park and 7 minutes from Shadmoor State Park.
On private beach
Pool
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
$168 nightly
The price is $192 total per night
$192 total
May 11 - May 12
Total with taxes and fees
20.31 mi from city center
When you stay at Montauk Manor in Montauk, you'll be near the beach, within a 15-minute drive of The Hamptons Beaches and Montauk Point.
Pool
Hot Tub
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$252 nightly
The price is $288 total per night
$288 total
May 3 - May 4
Total with taxes and fees
3.59 mi from city center
When you stay at Sound View Greenport in Greenport, you'll be by the ocean, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach.
On private beach
Pool
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd Montauk NY
$279 nightly
The price is $319 total per night
$319 total
Apr 28 - Apr 29
Total with taxes and fees
21.1 mi from city center
When you stay at Montauk Yacht Club in Montauk, you'll be on the waterfront, within a 15-minute drive of The Hamptons Beaches and Montauk Point.
On private beach
Pool
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
$164 nightly
The price is $187 total per night
$187 total
Apr 30 - May 1
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.71 mi from city center
When you stay at The Bentley Hotel Southampton in Southampton, you'll be near the airport, within a 5-minute drive of The Hamptons Beaches and Meschutt Beach.
Pool
Pet friendly
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street Sag Harbor NY
$225 nightly
The price is $257 total per night
$257 total
Apr 29 - Apr 30
Total with taxes and fees
5.05 mi from city center
When you stay at Sag Harbor Inn in Sag Harbor, you'll be near the beach, just steps from The Hamptons Beaches and 9 minutes by foot from Bay Street Theatre.
Pool
Breakfast included
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
$264 nightly
The price is $304 total per night
$304 total
May 20 - May 21
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
15.59 mi from city center
With a stay at Water's Edge Resort & Spa in Westbrook (Westbrook Center), you'll be a 4-minute drive from Tanger Outlets and 8 minutes from Clinton Crossing Premium Outlets.
On private beach
Pool
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
$224 nightly
The price is $256 total per night
$256 total
Apr 28 - Apr 29
Total with taxes and fees
2.61 mi from city center
When you stay at The Harbor Front Inn in Greenport, you'll be near the bay, just steps from Camera Obscura and Greenport Carousel.
Pool
Breakfast included
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
$213 nightly
The price is $240 total per night
$240 total
Apr 28 - Apr 29
Total with taxes and fees
3.44 mi from city center
When you stay at The Shoals Suites and Slips in Southold, you'll be near the bay, within a 5-minute drive of The Old Field Vineyards and Mattebella Vineyards.
Free WiFi
Air conditioning
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street Riverhead NY
$147 nightly
The price is $168 total per night
$168 total
May 6 - May 7
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
19.5 mi from city center
With a stay at Hyatt Place Long Island East End in Riverhead, you'll be on a river, within a 10-minute drive of Splish Splash Water Park and Suffolk Theater.
Pool
Pet friendly
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
$91 nightly
The price is $104 total per night
$104 total
May 3 - May 4
Total with taxes and fees
Free Cancellation
15.48 mi from city center
With a stay at Pier Blue Inn Old Saybrook - Essex in Old Saybrook (Saybrook Manor), you'll be within a 15-minute drive of Hammonasset Beach State Park and Chalker Beach.
Pet friendly
Parking included
Offshore Montauk

Offshore Montauk

2 out of 5
71 S Emerson Ave Montauk NY
$281 nightly
The price is $321 total per night
$321 total
Apr 28 - Apr 29
Total with taxes and fees
20.51 mi from city center
When you stay at Offshore Montauk in Montauk, you'll be in the business district, within a 15-minute drive of The Hamptons Beaches and Montauk Point.
Pool
Spa
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Shelter Island hotels essential information

Accommodation
4,764 hotels
Lowest Price
$104
Highest Price
$595
Popular hotels
Gurney's Montauk Resort & Seawater Spa, Montauk Manor, Sound View Greenport, Montauk Yacht Club, The Bentley Hotel Southampton, Sag Harbor Inn, Water's Edge Resort & Spa, The Harbor Front Inn, The Shoals Suites and Slips, Hyatt Place Long Island East End, Pier Blue Inn Old Saybrook - Essex, Offshore Montauk

Most Recent Shelter Island Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

3 out of 5
Posted 1 hour ago
CheapTickets Verified Review
"Good location"
A verified traveler stayed at Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex

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