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Nov 3 - Nov 4
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Nov 13 - Nov 15

Most frequently booked Shelter Island hotels

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
29.68 km from city centre
The price is CA $480 per night
CA $480
CA $658 total
Nov 9 - Nov 10
includes taxes & fees
Book a stay at this beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Popular attractions Hither Woods Preserve and Hither Hills State Park are located nearby.
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
Free cancellation
Reserve now, pay when you stay
25.1 km from city centre
The price is CA $227 per night
CA $227
CA $286 total
Nov 10 - Nov 11
includes taxes & fees
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Tanger Outlets and Westbrook Town Beach are located nearby.
On private beach
Pool
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Free cancellation
Reserve now, pay when you stay
24.93 km from city centre
The price is CA $108 per night
CA $108
CA $125 total
Nov 5 - Nov 6
includes taxes & fees
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. Popular attractions Chalker Beach and Crystal Lake Town Park are located nearby.
Pet-friendly
Parking included
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
21.48 km from city centre
The price is CA $145 per night
CA $145
CA $200 total
Nov 24 - Nov 25
includes taxes & fees
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 Cooper's Beach and Sebonack Golf Course are located nearby.
Pool
Pet-friendly
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
33.03 km from city centre
The price is CA $177 per night
CA $177
CA $282 total
Nov 8 - Nov 9
includes taxes & fees
Stay at this hotel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Montauk Point Lighthouse and Montauk Point are located nearby.
Pool
Pet-friendly
Montauk Blue Hotel

Montauk Blue Hotel

3 out of 5
108 South Emerson Avenue Montauk NY
33.29 km from city centre
The price is CA $200 per night
CA $200
CA $297 total
Nov 4 - Nov 5
includes taxes & fees
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, a beach locale, and daily housekeeping. Popular attractions Montauk Point Lighthouse and Montauk Point are located nearby.
Pool
Hot tub
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
5.79 km from city centre
The price is CA $213 per night
CA $213
CA $284 total
Nov 16 - Nov 17
includes taxes & fees
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Railroad Museum of Long Island and The Old Field Vineyards are located nearby.
On private beach
Pool
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
4.42 km from city centre
The price is CA $190 per night
CA $190
CA $217 total
Nov 11 - Nov 12
includes taxes & fees
Book a stay at this boutique hotel in Greenport. Enjoy free parking, free bicycles on site, and daily housekeeping. Popular attractions Greenport Harbor Brewing Company and Greenport Farmers' Market are located nearby.
Pet-friendly
Parking included
Montauk Yacht Club

Montauk Yacht Club

4.5 out of 5
32 Star Island Rd Montauk NY
33.98 km from city centre
The price is CA $348 per night
CA $348
CA $557 total
Nov 4 - Nov 5
includes taxes & fees
Book a stay at this luxury hotel in Montauk. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Montauk Point and Montauk Point Lighthouse are located nearby.
On private beach
Pool
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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.

Top hotels in Shelter Island for Extended Stay

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences

239 E Montauk Hwy Hampton Bays NY
10/10 Exceptional! (3 reviews)
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
4,547 hotels
Lowest Price
CA $125
Highest Price
CA $658
Popular hotels
Gurney's Montauk Resort & Seawater Spa, Water's Edge Resort & Spa, Pier Blue Inn Old Saybrook - Essex, The Atlantic Hotel, Offshore Montauk, Montauk Blue Hotel, Sound View Greenport, Zey Hotel, Montauk Yacht Club

Frequently asked questions

What are the top kid-friendly hotels in Shelter Island?
From carefully considered amenities to rooms with bunk beds, kid-friendly hotels come with features that can help transform a routine family vacation into an extraordinary one. These Shelter Island properties make getting away with children a breeze: You'll be well looked after at Beautifully renovated Farmhouse sitting on a lush property. It comes with a nearby beach, a travel crib and a flair for making families feel at home. Alternatively, spend your Shelter Island getaway at Paradise found on Shelter Island. Make the most of a playground, a nearby beach and more here.
Where can I find cheap hotels in Shelter Island?
At Travelocity you'll find really nice hotels in Shelter Island at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Shelter Island rather than in Shelter Island. We may find you even better rates, too.
How do I find the best Shelter Island hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Shelter Island then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Shelter Island?
The cheapest hotel in Shelter Island is CA $125 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Shelter Island?
There are 4,547 hotels in Shelter Island on Travelocity.
What are the best hotels in Shelter Island?
Shelter Island has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Shelter Island for you!
When is the best time to visit Shelter Island?
If you want the joy of a fun-filled trip in peak season, visit Shelter Island during May, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as January, October and December.
When is the cheapest time to stay in Shelter Island?
Based on historic data is usually the cheapest month to visit Shelter Island. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Shelter Island?
There are multiple hotels in Shelter Island that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Shelter Island. We have plenty of kid-friendly hotels in Shelter Island to choose from on Travelocity!
Why book a hotel in Shelter Island through Travelocity?
Because we have the top hotels in Shelter Island! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Shelter Island on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Shelter Island hotel reviews by fellow wanderers

Sound View Greenport

Sound View Greenport

5 out of 5
Posted 5 hours ago
Travelocity Verified Review
"Very well designed"
A verified traveller stayed at Sound View Greenport
Sound View Greenport