Book Cheap Hotels in Shelter Island

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Tonight
Check prices in Shelter Island for tonight, May 10 - May 11
May 10 - May 11
Tomorrow night
Check prices in Shelter Island for tomorrow night, May 11 - May 12
May 11 - May 12
This weekend
Check prices in Shelter Island for this weekend, May 10 - May 12
May 10 - May 12

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 $609 per night
CA $609
per night
May 12 - May 13
Stay at this 4-star beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Our guests praise the room service in our reviews. Popular attractions Hither Woods Preserve and Hither Hills State Park are located nearby.
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St., Montauk, NY
32.71 km from city centre
The price is CA $230 per night
CA $230
per night
May 14 - May 15
Stay at this 3.5-star spa aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the property condition in our reviews. Popular attractions Shadmoor State Park and Fort Pond are located nearby.
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street, Riverhead, NY
Free cancellation
31.4 km from city centre
The price is CA $208 per night
CA $208
per night
May 21 - May 22
Stay at this 3-star business-friendly hotel in Riverhead. Enjoy free WiFi, free parking, and a marina. Our guests praise the breakfast and the pool in our reviews. Popular attractions Splish Splash Water Park and Suffolk Theater are located nearby.
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Free cancellation
Reserve now, pay when you stay
27.92 km from city centre
The price is CA $122 per night
CA $122
per night
May 12 - May 13
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Ferry Landing State Park and Essex Saybrook Antique Village Shopping Center are located nearby.
Greenporter Hotel

Greenporter Hotel

2 out of 5
326 Front St, Greenport, NY
Free cancellation
Reserve now, pay when you stay
4.3 km from city centre
The price is CA $187 per night
CA $187
per night
May 12 - May 13
Stay at this hotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and East End Seaport Maritime Museum are located nearby.
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
Free cancellation
Reserve now, pay when you stay
23.94 km from city centre
The price is CA $414 per night
CA $414
per night
May 12 - May 13
Book a stay at this spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the restaurant in our reviews. Popular attractions General William Hart House and Katharine Hepburn Cultural Arts Center are located nearby.
The Niantic Inn

The Niantic Inn

2 out of 5
345 Main Street, Niantic, CT
Free cancellation
Reserve now, pay when you stay
30.76 km from city centre
The price is CA $270 per night
CA $270
per night
May 22 - May 23
Stay at this hotel in Niantic. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Ocean Beach Park and New London Ferry Dock are located nearby.
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street, Sag Harbor, NY
8.13 km from city centre
The price is CA $320 per night
CA $320
per night
May 13 - May 14
Stay at this 3.5-star business-friendly hotel in Sag Harbor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions The Hamptons Beaches and Sag Harbor Whaling and Historical Museum are located nearby.
The Sunset Montauk

The Sunset Montauk

2.5 out of 5
540 West Lake Drive, Montauk, NY
33.21 km from city centre
The price is CA $162 per night
CA $162
per night
May 12 - May 13
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Montauk Marine Basin and Gin Beach are located nearby.
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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

Windward Shores Ocean Resort

Windward Shores Ocean Resort

2062 Montauk Highway, PO Box 7031, Amagansett, NY
The price is CA $210 per night from May 12 to May 13
CA $210
per night
May 12 - May 13
8.6/10 Excellent! (233 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.

Cheap Hotels in Shelter Island

Pack your bags—it’s time to embark on a getaway. Whether you’re craving a solo retreat or promising your family a vacation to remember, book one of the best hotels in Shelter Island. These hotels are located within easy access of the city’s hottest attractions and entertainment, so you won’t miss a beat while you’re in town. Spend the days exploring the local landmarks and the evenings getting to know the nightlife. After exploring the city from top to bottom, rest up at a hotel that speaks to you. Find the perfect place that matches your trip’s vibe, from a trendy boutique to family-friendly accommodations.

Allow us here at Travelocity to pair you with up Shelter Island hotels that suit your vacation preferences. Discover places with convenient on-site restaurants, around-the-clock service, and pools where your kids can make a splash. Some hotels may boast fitness rooms and spa services, while others feature game rooms and Wi-Fi access. To top it all off, you’ll score cheap hotels in Shelter Island that let you spend more on your activities and less on your lodging. Book and bundle your flight and hotel deals together today and save $$$. It’s time to explore a new city, and break out of your routine.

Shelter Island hotels essential information

Accommodation
4,792 hotels
Lowest Price
CA $122
Highest Price
CA $609
Popular hotels
Gurney's Montauk Resort & Seawater Spa, Montauk Manor, Hyatt Place Long Island East End, Quality Inn Old Saybrook - Westbrook, Greenporter Hotel, Saybrook Point Resort & Marina, The Niantic Inn, Sag Harbor Inn, The Sunset Montauk

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 $122 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 4,792 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

The Sunset Montauk

The Sunset Montauk

5 out of 5
Posted 23 hours ago
Travelocity Verified Review
"This play was exceptionally clean, especially for a beach hotel. Also the grounds were well kept and child friendly and the room rate was affordable. Would definitely stay there again!"
A verified traveller stayed at The Sunset Montauk
The Sunset Montauk

Types of hotels

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Areas of Shelter Island