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Cheap Shelter Island Hotels
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
$466 nightly
The price is $532 total per night
$532 total
Dec 15 - Dec 16
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
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
$244 nightly
The price is $281 total per night
$281 total
Dec 15 - Dec 16
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
$79 nightly
The price is $91 total per night
$91 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
15.48 mi from city center
Located in Old Saybrook (Saybrook Manor), Pier Blue Inn Old Saybrook - Essex is within a 5-minute drive of Chalker Beach and Saybrook Country Barn.
Pet friendly
Parking included
Sound View Greenport
58775 County Rd 48 Greenport NY
$212 nightly
The price is $242 total per night
$242 total
Jan 13 - Jan 14, 2026
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 Blue Hotel
108 South Emerson Avenue Montauk NY
20.67 mi from city center
With a stay at Montauk Blue Hotel in Montauk (Downtown Montauk), you'll be steps from The Hamptons Beaches and South Edison Beach.
Pool
Hot Tub
Offshore Montauk
71 S Emerson Ave Montauk NY
$166 nightly
The price is $190 total per night
$190 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
20.51 mi from city center
When you a stay at Offshore Montauk in Montauk, you'll be near the beach, just steps from The Hamptons Beaches and Kirk Park Beach.
Pool
Pet friendly
Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
$331 nightly
The price is $380 total per night
$380 total
Dec 15 - Dec 16
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
14.87 mi from city center
With a stay at Saybrook Point Resort & Marina in Old Saybrook (Old Saybrook Center), you'll be steps from Fort Saybrook Monument Park and 4 minutes by foot from Connecticut River.
Pool
Hot Tub
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
$126 nightly
The price is $144 total per night
$144 total
Dec 21 - Dec 22
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
Quality Inn Old Saybrook - Westbrook
100 Essex Rd Old Saybrook CT
$101 nightly
The price is $116 total per night
$116 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
17.34 mi from city center
A stay at Quality Inn Old Saybrook - Westbrook places you in the heart of Old Saybrook, a 5-minute drive from Essex Steam Train and 5 minutes from Essex Library.
Pool
Breakfast included
Montauk Manor
236 Edgemere St. Montauk NY
$156 nightly
The price is $178 total per night
$178 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
20.31 mi from city center
With a stay at Montauk Manor in Montauk, you'll be near the beach, just a 3-minute walk from Shadmoor State Park and 14 minutes by foot from The Hamptons Beaches.
Pool
Hot Tub
Beachcomber Resort at Montauk
727 Old Montauk Highway Montauk NY
19.93 mi from city center
With a stay at Beachcomber Resort at Montauk in Montauk, you'll be near the beach, just a 1-minute walk from The Hamptons Beaches and 8 minutes by foot from Second House Museum.
Pool
Free WiFi
The Harbor Front Inn
209 Front St Greenport NY
$178 nightly
The price is $203 total per night
$203 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
2.61 mi from city center
When you a 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
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.
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Shelter Island hotels essential information
Accommodation | 4,687 hotels |
|---|---|
Lowest Price | $91 |
Highest Price | $532 |
Popular hotels | Gurney's Montauk Resort & Seawater Spa, Water's Edge Resort & Spa, Pier Blue Inn Old Saybrook - Essex, Sound View Greenport, Montauk Blue Hotel, Offshore Montauk, Saybrook Point Resort & Marina, The Bentley Hotel Southampton, Quality Inn Old Saybrook - Westbrook, Montauk Manor, Beachcomber Resort at Montauk, The Harbor Front Inn |
Most Recent Shelter Island Hotel Reviews
Water's Edge Resort & Spa
5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"The staff were all pleasant and helpful. View from the room was amazing. Place was decorated beautifully for Christmas. Beautiful wood burning fireplaces to sit by and relax. The perfect cold weather getaway"
A verified traveler stayed at Water's Edge Resort & Spa
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