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Cheap Shelter Island Hotels

Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
$594 nightly
The price is $679 total per night
$679 total
May 3 - May 4
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
236 Edgemere St. Montauk NY
$168 nightly
The price is $192 total per night
$192 total
May 18 - May 19
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

Montauk Yacht Club
32 Star Island Rd Montauk NY
$299 nightly
The price is $341 total per night
$341 total
May 11 - May 12
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

Sound View Greenport
58775 County Rd 48 Greenport NY
$304 nightly
The price is $347 total per night
$347 total
May 25 - May 26
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

Quality Inn Old Saybrook - Westbrook
100 Essex Rd Old Saybrook CT
$118 nightly
The price is $136 total per night
$136 total
May 25 - May 26
Total with taxes and fees
Free Cancellation
17.32 mi from city center
A stay at Quality Inn Old Saybrook - Westbrook places you in the heart of Old Saybrook, within a 10-minute drive of Essex Steam Train and Essex Library.
Pool
Breakfast included

The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
$145 nightly
The price is $166 total per night
$166 total
May 7 - May 8
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
45 West Water Street Sag Harbor NY
$255 nightly
The price is $291 total per night
$291 total
May 3 - May 4
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
1525 Boston Post Road Westbrook CT
$264 nightly
The price is $304 total per night
$304 total
May 8 - May 9
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

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
$91 nightly
The price is $104 total per night
$104 total
May 7 - May 8
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

The Harbor Front Inn
209 Front St Greenport NY
$264 nightly
The price is $302 total per night
$302 total
May 19 - May 20
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

Hyatt Place Long Island East End
451 East Main Street Riverhead NY
$159 nightly
The price is $182 total per night
$182 total
May 7 - May 8
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

The Shoals Suites and Slips
61600 Main Rd Southold NY
$213 nightly
The price is $240 total per night
$240 total
May 3 - May 4
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
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.
Shelter Island hotels essential information
Accommodation | 4,778 hotels |
|---|---|
Lowest Price | $104 |
Highest Price | $679 |
Popular hotels | Gurney's Montauk Resort & Seawater Spa, Montauk Manor, Montauk Yacht Club, Sound View Greenport, Quality Inn Old Saybrook - Westbrook, The Bentley Hotel Southampton, Sag Harbor Inn, Water's Edge Resort & Spa, Pier Blue Inn Old Saybrook - Essex, The Harbor Front Inn, Hyatt Place Long Island East End, The Shoals Suites and Slips |
Most Recent Shelter Island Hotel Reviews

Montauk Manor
5 out of 5
Posted 10 hours ago
CheapTickets Verified Review
"Great locations for sunset."
A verified traveler stayed at Montauk Manor






