Compare Cheap Hotels in Shelter Island

Secret Bargains - Save an extra 10% or more on select hotels

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Cheap Shelter Island Hotels

Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd, Montauk, NY
$400 nightly
The price is $457 total per night
$457 total
May 26 - May 27
Total includes 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
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue, Montauk, NY
$180 nightly
The price is $205 total per night
$205 total
May 27 - May 28
Total includes taxes and fees
20.67 mi from city center
When you stay at Montauk Blue Hotel in Montauk, you'll be on the beach, within a 15-minute drive of The Hamptons Beaches and Montauk Point.
Pool
Hot Tub
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St., Montauk, NY
$185 nightly
The price is $212 total per night
$212 total
May 27 - May 28
Total includes 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
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway, Montauk, NY
$627 nightly
The price is $717 total per night
$717 total
May 26 - May 27
Total includes 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

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road, Westbrook, CT
$244 nightly
The price is $281 total per night
$281 total
May 26 - May 27
Total includes 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 Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
$211 nightly
The price is $241 total per night
$241 total
May 26 - May 27
Total includes taxes and fees
13.36 mi from city center
When you stay at The Atlantic Hotel in Southampton, you'll be in the business district, within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.
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
$87 nightly
The price is $100 total per night
$100 total
May 26 - May 27
Total includes 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 Crystal Lake Town Park.
Pet friendly
Parking included
Baron's Cove

Baron's Cove

4 out of 5
31 West Water Street, Sag Harbor, NY
$260 nightly
The price is $297 total per night
$297 total
May 28 - May 29
Total includes taxes and fees
5.06 mi from city center
When you stay at Baron's Cove in Sag Harbor, you'll be near the beach, just steps from The Hamptons Beaches and 7 minutes by foot from Bay Street Theatre.
Pool
Spa
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street, Riverhead, NY
$172 nightly
The price is $197 total per night
$197 total
May 26 - May 27
Total includes 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
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street, Sag Harbor, NY
$305 nightly
The price is $348 total per night
$348 total
May 26 - May 27
Total includes 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
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

3 out of 5
727 Old Montauk Highway, Montauk, NY
$280 nightly
The price is $316 total per night
$316 total
May 27 - May 28
Total includes taxes and fees
19.93 mi from city center
Located in Montauk, Beachcomber Resort at Montauk is within a 15-minute drive of The Hamptons Beaches and Montauk Point.
Pool
Free WiFi
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd, Southampton, NY
$216 nightly
The price is $247 total per night
$247 total
May 26 - May 27
Total includes 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
Don't see what you're looking for?
See all available properties in Shelter Island
View all properties
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.

Often, one of the most difficult things about booking a hotel is finding the best time to go. The cost of staying in hotels in could vary significantly, depending on the time of the year chosen. If you would like to figure out the most suitable time to take a trip then using CheapTickets could be the best option for you. We will be able to provide information on hotels in to ensure that you get the best deal possible. So if you are looking for a booking website that will streamline the process and offer good prices, then log in and get booking.

Shelter Island hotels essential information

Accommodation
4,784 hotels
Lowest Price
$100 total
Highest Price
$717 total
Popular hotels
Montauk Yacht Club, Montauk Blue Hotel, Montauk Manor, Gurney's Montauk Resort & Seawater Spa, Water's Edge Resort & Spa, The Atlantic Hotel, Pier Blue Inn Old Saybrook - Essex, Baron's Cove, Hyatt Place Long Island East End, Sag Harbor Inn, Beachcomber Resort at Montauk, The Bentley Hotel Southampton

Most Recent Shelter Island Hotel Reviews

Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"I can’t say enough about how wonderful my stay was. Beautiful views. Short walk to ocean. Clean nice room. Hot shower water. It has a stove in the room if needed. Huge screen tv. It is very close to perfect. I definitely recommend. The staff are very friendly and helpful. "
A verified traveler stayed at Beachcomber Resort at Montauk
Beachcomber Resort at Montauk