Book Cheap Hotels in Shelter Island

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Most frequently booked Shelter Island hotels

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free cancellation

Reserve now, pay when you stay

24.93 km from city centre

CA $115

CA $132 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

290 Old Montauk Highway Montauk NY

29.68 km from city centre

CA $515

CA $706 total

Sep 29 - Sep 30

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

Offshore Montauk

71 S Emerson Ave Montauk NY

33.03 km from city centre

CA $218

CA $329 total

Sep 29 - Sep 30

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

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

Free cancellation

Reserve now, pay when you stay

25.1 km from city centre

CA $252

CA $314 total

Oct 7 - Oct 8

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

Sound View Greenport

58775 County Rd 48 Greenport NY

5.79 km from city centre

CA $344

CA $433 total

Oct 14 - Oct 15

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 Hashamomuck Pond and Railroad Museum of Long Island are located nearby.

On private beach

Pool

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY

33.29 km from city centre

CA $171

CA $264 total

Oct 20 - Oct 21

includes taxes & fees

Book a stay at this beach hotel in Montauk. Enjoy a beach locale, daily housekeeping, and a picnic area. Popular attractions Montauk Point Lighthouse and Montauk Point are located nearby.

Pool

Hot tub

The Atlantic Hotel

1655 County Road 39 Southampton NY

21.48 km from city centre

CA $168

CA $227 total

Oct 1 - Oct 2

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

Ocean Surf Resort

84 South Emerson Avenue Montauk NY

33.16 km from city centre

CA $138

CA $219 total

Sep 29 - Sep 30

includes taxes & fees

Book a stay at this beach motel in Montauk. Enjoy free WiFi, an outdoor pool, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Montauk Point Lighthouse and Montauk Point are located nearby.

Pool

Free WiFi

Ocean Resort Inn

95 S Emerson Ave Montauk NY

33.19 km from city centre

CA $218

CA $249 total

Sep 27 - Sep 28

includes taxes & fees

Book a stay at this beach motel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Montauk Point Lighthouse and Montauk Point are located nearby.

Pool

Parking included

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See all available properties in Shelter Island

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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

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	4,628 hotels
Lowest Price	CA $132
Highest Price	CA $706
Popular hotels	Pier Blue Inn Old Saybrook - Essex, Gurney's Montauk Resort & Seawater Spa, Offshore Montauk, Water's Edge Resort & Spa, Sound View Greenport, Montauk Blue Hotel, The Atlantic Hotel, Ocean Surf Resort, Ocean Resort 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 $132 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 4,628 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

Water's Edge Resort & Spa

4 out of 5

Posted less than an hour ago

Travelocity Verified Review

"The staff at the Bistro Bar weren't very good. Also the drinks sub par. I ordered a gin and tonic, they served me soda water twice."

A verified traveller stayed at Water's Edge Resort & Spa

Ocean Surf Resort

5 out of 5

Posted less than an hour ago

Travelocity Verified Review

"it was a lovely stay at the Ocean surf resort. We went in September and the weather was spectacular. We really enjoyed watching the sea life from the deck. We saw so many whales, dolphins and seals too. It was quiet enough to get a night's sleep and the mattress was pretty good too. My only issue was the kitchenette- which was there but not usable. There is no counter space at all. I really think that the rooms need to be reconfigured. There was a nice working little fridge. We never used the stove top (I think that it should be taken out) or just mount the microwave. But all in all, we would stay here again."

A verified traveller stayed at Ocean Surf Resort