Book Cheap Hotels in Shelter Island

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Most frequently booked Shelter Island hotels

Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount

Shelter Island NY
2.13 km from city centre
Get rates
Stay at this vacation home in Shelter Island. Enjoy free WiFi, private pools, and a garden. Popular attractions Wades Beach and Mashomack Preserve are located nearby.
Pool
Kitchen
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 $447 per night
CA $447
CA $614 total
Jan 20 - Jan 21
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 $314 per night
CA $314
CA $385 total
Jan 4 - Jan 5
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
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue Montauk NY
33.29 km from city centre
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Book a stay at this beach hotel in Montauk. Enjoy free WiFi, a beach locale, and parking (surcharge). Popular attractions South Edison Beach and Kirk Park Beach are located nearby.
Pool
Hot tub
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
Get rates
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 Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Free cancellation
Reserve now, pay when you stay
22.07 km from city centre
The price is CA $169 per night
CA $169
CA $194 total
Jan 22 - Jan 23
includes taxes & fees
Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sebonack Golf Course and Shinnecock Hills Golf Course are located nearby.
Pool
Pet-friendly
Offshore Montauk

Offshore Montauk

2 out of 5
71 S Emerson Ave Montauk NY
33.03 km from city centre
The price is CA $159 per night
CA $159
CA $260 total
Jan 14 - Jan 15
includes taxes & fees
Stay at this hotel in Montauk. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Kirk Park Beach and South Edison Beach are located nearby.
Pool
Pet-friendly
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
32.71 km from city centre
The price is CA $190 per night
CA $190
CA $244 total
Jan 5 - Jan 6
includes taxes & fees
Stay at this aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Shadmoor State Park and Fort Pond are located nearby.
Pool
Hot tub
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
4.2 km from city centre
The price is CA $185 per night
CA $185
CA $251 total
Feb 1 - Feb 2
includes taxes & fees
Book a stay at this business-friendly hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Greenport Carousel and Camera Obscura are located nearby.
Pool
Breakfast included
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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

The modern farmhouse view

The modern farmhouse view

East Quogue NY
10/10 Exceptional! (9 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
4,685 hotels
Lowest Price
CA $194
Highest Price
CA $614
Popular hotels
Work and Play Special! Extended Stay Discount , Gurney's Montauk Resort & Seawater Spa, Water's Edge Resort & Spa, Montauk Blue Hotel, Pier Blue Inn Old Saybrook - Essex, The Bentley Hotel Southampton, Offshore Montauk, Montauk Manor, The Harbor Front Inn

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 $194 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 4,685 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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Friendly staff, and relaxing spa"
A verified traveller stayed at Saybrook Point Resort & Marina
Saybrook Point Resort & Marina

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Areas of Shelter Island