Find hotels in Shelter Island, NY from ฿2,540

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Top 10 Shelter Island hotels and places to stay

Our top choices for Shelter Island hotels

Liberty Inn
Property grounds

Liberty Inn

2.0 star property
7.4 out of 10, Good, (624)
"Service at front desk was very good!"
The price is ฿2,826
฿3,250 total
includes taxes & fees
23 Sept - 24 Sept
Liberty Inn
Hampton Bays Hotel on Main
Deluxe Double Room, 1 King Bed, City View | In-room safe, individually decorated, individually furnished, desk

Hampton Bays Hotel on Main

2.0 star property
7.0 out of 10, Good, (58)
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
Hampton Bays Hotel on Main
Greenporter Hotel
Property grounds

Greenporter Hotel

2.0 star property
9.2 out of 10, Wonderful, (221)
"Great location, great hotel, great staff! "
Greenporter Hotel
Kenny's Tipperary Inn
Seasonal outdoor pool, pool umbrellas, pool loungers

Kenny's Tipperary Inn

2.0 star property
8.4 out of 10, Very good, (841)
"loved the pet friendly aspect "
Kenny's Tipperary Inn
Aqualina Inn Montauk
Seasonal outdoor pool, pool loungers

Aqualina Inn Montauk

2.5 star property
9.6 out of 10, Exceptional, (477)
"Great location walkable to beach shopping & restaurants."
The price is ฿4,091
฿5,191 total
includes taxes & fees
24 Sept - 25 Sept
Aqualina Inn Montauk
Econo Lodge Inn & Suites Old Saybrook Westbrook
Exterior

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
7.2 out of 10, Good, (448)
" Continental breakfast with sub optimal only waffles nothing else And eight bananas to start"
The price is ฿2,411
฿2,773 total
includes taxes & fees
23 Sept - 24 Sept
Econo Lodge Inn & Suites Old Saybrook Westbrook
A Wave Inn
Beach

A Wave Inn

2.5 star property
7.4 out of 10, Good, (129)
"Great place to relax and enjoy Montauk!"
The price is ฿2,908
฿5,798 total
includes taxes & fees
15 Sept - 16 Sept
A Wave Inn
Clinton Motel
Property grounds

Clinton Motel

2.5 star property
8.6 out of 10, Excellent, (271)
"Great stay. Fantastic location. Wonderful motel providing everything you need. Clean, comfortable and excellent value."
The price is ฿2,475
฿2,847 total
includes taxes & fees
14 Sept - 15 Sept
Clinton Motel
Pier Blue Inn Old Saybrook - Essex
Property grounds

Pier Blue Inn Old Saybrook - Essex

2.0 star property
7.8 out of 10, Good, (1000)
"Good budget friendly hotel"
The price is ฿2,540
฿2,922 total
includes taxes & fees
15 Sept - 16 Sept
Pier Blue Inn Old Saybrook - Essex
Ocean Surf Resort
View from property

Ocean Surf Resort

2.0 star property
8.4 out of 10, Very good, (198)
"Great location, amazing view, clean, friendly and helpful staff."
The price is ฿4,188
฿4,784 total
includes taxes & fees
5 Oct - 6 Oct
Ocean Surf Resort
Lamplighter Motel - Clinton, Connecticut
Exterior

Lamplighter Motel - Clinton, Connecticut

2.5 star property
6.2 out of 10, (215)
"Would stay again. "
The price is ฿2,188
฿2,517 total
includes taxes & fees
14 Sept - 15 Sept
Lamplighter Motel - Clinton, Connecticut
Shorewood Inn
Terrace/patio

Shorewood Inn

2.5 star property
8.4 out of 10, Very good, (681)
"Good place to stay"
Shorewood Inn
The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, pool loungers

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (77)
"Shelter Island is definitely a gem"
The price is ฿11,968
฿15,040 total
includes taxes & fees
14 Sept - 15 Sept
The Pridwin Hotel
House on Chase Creek
View from property

House on Chase Creek

2.5 star property
9.4 out of 10, Exceptional, (76)
"The House on Chase Creek is beautiful. It's an old house but everything is updated, clean and comfortable. "
The price is ฿6,832
฿7,806 total
includes taxes & fees
13 Oct - 14 Oct
House on Chase Creek
Offshore Montauk
View from room

Offshore Montauk

2.0 star property
9.2 out of 10, Wonderful, (47)
"Robert was a pleasure to deal with and made it a seamless stay"
The price is ฿7,112
฿11,751 total
includes taxes & fees
1 Oct - 2 Oct
Offshore Montauk
Saybrook Point Resort & Marina
Exterior

Saybrook Point Resort & Marina

3.5 star property
9.4 out of 10, Exceptional, (1002)
"Great spot. Good restaurants in the area"
The price is ฿11,255
฿13,737 total
includes taxes & fees
12 Oct - 13 Oct
Saybrook Point Resort & Marina
Ruschmeyers
Exterior

Ruschmeyers

3.0 star property
8.2 out of 10, Very good, (72)
"Cool rooms and grounds. Lots of great common outdoor spaces. "
The price is ฿6,708
฿8,430 total
includes taxes & fees
22 Sept - 23 Sept
Ruschmeyers
Inn at Harbor Hill Marina
Property grounds

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1000)
"Homestyle welcome in an incredibly cosy inn!"
The price is ฿7,263
฿8,352 total
includes taxes & fees
1 Oct - 2 Oct
Inn at Harbor Hill Marina
Ocean Resort Inn
On the beach, sun-loungers, beach umbrellas, beach towels

Ocean Resort Inn

2.0 star property
9.6 out of 10, Exceptional, (453)
"Great location and great staff "
The price is ฿4,094
฿5,194 total
includes taxes & fees
28 Sept - 29 Sept
Ocean Resort Inn
Breakers Montauk
Exterior

Breakers Montauk

3.0 star property
8.6 out of 10, Excellent, (169)
"This was my fourth time here and I always have an enjoyable stay. The pool area is lovely and the property is well maintained. I would recommend this place!"
The price is ฿4,008
฿5,613 total
includes taxes & fees
28 Sept - 29 Sept
Breakers Montauk
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.
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Where to stay in Shelter Island

Find the best Shelter Island areas for the activities you enjoy most.

Silver Beach

While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.

Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Sunset Beach and Crescent Beach.

Coecles Harbor

While Coecles Harbor isn't home to many top sights, Gardiner's Bay Country Club and Sunset Beach are some notable places to visit nearby.

Hay Beach

When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.

Shorewood

While Shorewood may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach.

Learn more about Shelter Island

Escape to Shelter Island! Enjoy its island views, natural setting and beaches.

See all hotels in Shelter Island
Photo by tom owens
Open Photo by tom owens

Top Shelter Island Hotel Reviews

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Thank you for such a wonderful vocation! We enjoyed our stay, and would go back there again."
Luiza Torab 2-night trip
Posted 3 days ago
Montauk Yacht Club

More cheap stays in Shelter Island

More cheap stays in Shelter Island

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

100 Essex Rd, Old Saybrook, CT
The price is ฿3,100 per night from 23 Sept to 24 Sept
฿3,100
฿3,565 total
23 Sept - 24 Sept
includes taxes & fees
7.6/10 Good! (1,003 reviews)

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Where is the best place to stay in Shelter Island?

Located 15.5 mi (24.9 km) from the heart of Shelter Island, Pier Blue Inn Old Saybrook - Essex is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Montauk Yacht Club and The Atlantic Hotel. See all available top hotels, or vacation rentals in Shelter Island.

If I need to cancel my hotel reservation in Shelter Island, will I receive a refund?

Yes! You'll find that most hotel bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If your reservation is non-refundable, you might be able to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Shelter Island.

What's the best dog-friendly accommodation option in Shelter Island?

Sunset Beach Hotel is a top hotel for people travelling with their pets, and offers a restaurant and free WiFi for its human guests. See more pet-friendly hotel accommodations in Shelter Island.

What's the best hotel to stay near the beach in Shelter Island?

Sunset Beach Hotel is a top beachfront hotel with free WiFi and free parking, and it's located on Sunset Beach . See more stays near the beach in Shelter Island.

What are some accommodation options with pools in Shelter Island?

Montauk Yacht Club: Hotel, 5-minute walk from The Hamptons Beaches. Offers 2 outdoor swimming pools, a children's pool and a private beach. The Atlantic Hotel and Marram are a couple of other choices that offer an on-site pool. View all hotels with pools in Shelter Island.

What's it like to stay in Shelter Island?

Visitors can enjoy all that Shelter Island has to offer, including the parks, beaches and museums. This city also attracts tourists with its scenic landscape. In Shelter Island, there are 95 hotels and other accommodation options to choose from. Find out more about Shelter Island.

What should I see while I'm in Shelter Island?

Natural beauty is on display at Sunset Beach, Crescent Beach and Wades Beach. A couple of additional sights to add to your itinerary are Gardiner's Bay Country Club and Shelter Island Historical Society. Take a look at what more there is to see and do in Expedia's Shelter Island guide.

What's the seasonal weather in Shelter Island?

The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Shelter Island is 1452 mm.