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Tonight
Check prices in Shelter Island for tonight, May 26 - May 27
May 26 - May 27
Tomorrow night
Check prices in Shelter Island for tomorrow night, May 27 - May 28
May 27 - May 28
This weekend
Check prices in Shelter Island for this weekend, May 29 - May 31
May 29 - May 31
Next weekend
Check prices in Shelter Island for next weekend, Jun 5 - Jun 7
Jun 5 - Jun 7

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 $786 per night
CA $786
CA $1,077 total
May 31 - Jun 1
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
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
32.71 km from city centre
The price is CA $199 per night
CA $199
CA $254 total
May 27 - May 28
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
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd Montauk NY
33.98 km from city centre
The price is CA $385 per night
CA $385
CA $598 total
May 27 - May 28
includes taxes & fees
Book a stay at this beach 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 Marine Basin and Gin Beach are located nearby.
On private beach
Pool
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
22.07 km from city centre
The price is CA $275 per night
CA $275
CA $348 total
May 27 - May 28
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 Cooper's Beach and Sebonack Golf Course are located nearby.
Pool
Pet-friendly
Marram

Marram

4 out of 5
21 Oceanview Terrace Montauk NY
33.85 km from city centre
The price is CA $367 per night
CA $367
CA $695 total
May 31 - Jun 1
includes taxes & fees
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions South Edison Beach and Kirk Park Beach are located nearby.
Pool
Parking included
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 $373 per night
CA $373
CA $545 total
May 27 - May 28
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
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 $254 per night
CA $254
CA $343 total
May 27 - May 28
includes taxes & fees
Book a stay at this beach hotel in Montauk. Enjoy a beach locale, daily housekeeping, and a picnic area. Popular attractions South Edison Beach and Kirk Park Beach are located nearby.
Pool
Hot tub
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 $435 per night
CA $435
CA $497 total
Jun 1 - Jun 2
includes taxes & fees
Book a stay at this 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.
Pool
Breakfast included
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
25.1 km from city centre
The price is CA $293 per night
CA $293
CA $361 total
Jun 1 - Jun 2
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
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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
4,815 hotels
Lowest Price
CA $254
Highest Price
CA $1,077
Popular hotels
Gurney's Montauk Resort & Seawater Spa, Montauk Manor, Montauk Yacht Club, The Bentley Hotel Southampton, Marram, Sound View Greenport, Montauk Blue Hotel, Sag Harbor Inn, Water's Edge Resort & Spa

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 $254 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 4,815 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

Montauk Manor

Montauk Manor

5 out of 5
Posted 4 hours ago
Travelocity Verified Review
"Extremely comfortable and clean. The Deluxe Studio is one of my favorite rooms I’ve ever stayed in at a hotel. The view was incredible, the staff were so friendly, and Monte’s was amazing. I can’t wait to come back here!"
A verified traveller stayed at Montauk Manor
Montauk Manor