Book Cheap Hotels in Shelter Island

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Tonight
Check prices in Shelter Island for tonight, Sep 26 - Sep 27
Sep 26 - Sep 27
Tomorrow night
Check prices in Shelter Island for tomorrow night, Sep 27 - Sep 28
Sep 27 - Sep 28
This weekend
Check prices in Shelter Island for this weekend, Sep 26 - Sep 28
Sep 26 - Sep 28

Most frequently booked Shelter Island hotels

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 $111 per night
CA $111
CA $128 total
Sep 29 - Sep 30
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
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 $542 per night
CA $542
CA $740 total
Sep 29 - Sep 30
includes taxes & fees
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.
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
The price is CA $204 per night
CA $204
CA $234 total
Oct 26 - Oct 27
includes taxes & fees
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, a beach locale, and parking (surcharge). Popular attractions Montauk Point and South Edison Beach 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 $346 per night
CA $346
CA $464 total
Oct 27 - Oct 28
includes taxes & fees
Stay at this 4-star 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
Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
33.85 km from city centre
The price is CA $252 per night
CA $252
CA $415 total
Oct 6 - Oct 7
includes taxes & fees
Stay at this 4-star beach hotel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Montauk Point and South Edison Beach are located nearby.
Pool
Parking included
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St., Montauk, NY
32.71 km from city centre
The price is CA $414 per night
CA $414
CA $500 total
Oct 24 - Oct 25
includes taxes & fees
Stay at this 3.5-star 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 Montauk Point and Shadmoor State Park are located nearby.
Pool
Hot tub
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
21.51 km from city centre
Get rates
Book a stay at this business-friendly hotel in Southampton. Enjoy free breakfast, free WiFi, and free parking. 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

2 out of 5
71 S Emerson Ave, Montauk, NY
33.03 km from city centre
The price is CA $206 per night
CA $206
CA $395 total
Oct 19 - Oct 20
includes taxes & fees
Stay at this hotel in Montauk. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Montauk Point and Kirk Park Beach are located nearby.
Pool
Pet-friendly
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 $489 per night
CA $489
CA $597 total
Oct 14 - Oct 15
includes taxes & fees
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Fort Saybrook Monument Park and General William Hart House are located nearby.
Pool
Hot tub
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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

Montauk Manor

Montauk Manor

236 Edgemere St., Montauk, NY
The price is CA $414 per night from Oct 24 to Oct 25
CA $414
CA $500 total
Oct 24 - Oct 25
includes taxes & fees
9/10 Wonderful! (1,250 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
4,719 hotels
Lowest Price
CA $128
Highest Price
CA $740
Popular hotels
Pier Blue Inn Old Saybrook - Essex, Gurney's Montauk Resort & Seawater Spa, Montauk Blue Hotel, Sound View Greenport, Marram, Montauk Manor, The Atlantic Hotel, Offshore Montauk, Saybrook Point Resort & Marina

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 $128 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 4,719 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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

5 out of 5
Posted 5 days ago
Travelocity Verified Review
"Highly recommend!"
A verified traveller stayed at Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex

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Areas of Shelter Island