Chestertown Hotel Guide. Hotels in Chester Shores, Chestertown, United States of America

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
18 Jul - 19 Jul
Tomorrow
19 Jul - 20 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Filter by

Guest rating
Guest rating
Property class

Top Trending Hotels Near Chester Shores, Chestertown

Silver Bay YMCA Inn and Conference Center
Enjoy a leisurely swim in the calm waters, surrounded by a lifeguard tower and scenic views.

Silver Bay YMCA Inn and Conference Center

3.0 star property
8.6 out of 10, Excellent, (96)
"Beautiful area , very close to the lake . "
The price is €145
includes taxes & fees
18 Aug - 19 Aug
Silver Bay YMCA Inn and Conference Center
Trout House Village Resort
Cozy cabin interior with a stone fireplace, dining area, and comfortable seating.

Trout House Village Resort

3.0 star property
9.8 out of 10, Exceptional, (12)
The price is €260
includes taxes & fees
21 Jul - 22 Jul
Trout House Village Resort
The Villas on Lake George
Enjoy serene lakeside views from the comfort of a classic lakeside retreat, featuring a well-maintained lawn and comfortable seating areas.

The Villas on Lake George

2.5 star property
7.6 out of 10, Good, (81)
"Great place for family get away . Beautiful location lake front beach and the pool. Our tradition every year to visit Lake George "
The price is €1,577
includes taxes & fees
26 Jul - 27 Jul
The Villas on Lake George
The Juliana Resort
Enjoy a drink at the outdoor seating area with a view of the lake.

The Juliana Resort

2.5 star property
8.8 out of 10, Excellent, (161)
"Beautiful property! Lake view was amazing. "
The price is €267
includes taxes & fees
17 Aug - 18 Aug
The Juliana Resort
Depe Dene Lakeside Resort
Enjoy meals in this dining area with a large table, chairs, and a chandelier.

Depe Dene Lakeside Resort

2.0 star property
8.8 out of 10, Excellent, (322)
"Great stay!"
Depe Dene Lakeside Resort
Amber Lantern Lake George Motel and Cottage Rentals
Relax on the porch with a view of the well-maintained lawn.

Amber Lantern Lake George Motel and Cottage Rentals

2.0 star property
8.4 out of 10, Very good, (287)
"The room was very nice, clean and had everything we needed. We had an efficiency. "
Amber Lantern Lake George Motel and Cottage Rentals
The Stone Gate Resort
Relax on the serene lakeside beach with a dock and comfortable Adirondack chairs.

The Stone Gate Resort

3.0 star property
9.6 out of 10, Exceptional, (83)
"Nicely updated family run property!"
The price is €344
includes taxes & fees
20 Jul - 21 Jul
The Stone Gate Resort
Lodges At Cresthaven
Guests can enjoy stunning lake views from the balconies of our lakeside cabins, surrounded by lush greenery and a well-manicured lawn.

Lodges At Cresthaven

4.0 star property
9.4 out of 10, Exceptional, (478)
"Wonderful trip and wonderful resort! "
Lodges At Cresthaven
Sun Castle Resort
Enjoy meals in this elegant dining room with a view of the outdoors.

Sun Castle Resort

3.5 star property
9.0 out of 10, Wonderful, (60)
"This please just was awesome! it was clean and organized! "
The price is €670
includes taxes & fees
14 Aug - 15 Aug
Sun Castle Resort
Doray Motel
Relax amidst a serene pine tree and well-manicured grass, perfect for a peaceful picnic.

Doray Motel

2.0 star property
8.4 out of 10, Very good, (161)
"I really like this cute motel "
The price is €85
includes taxes & fees
12 Aug - 13 Aug
Doray Motel
Boulder's Resort
Relax on the lakeside deck with lounge chairs and a table, taking in the serene views of the lake and surrounding greenery.

Boulder's Resort

2.0 star property
8.6 out of 10, Excellent, (33)
"Everything was so nice "
Boulder's Resort
Tea Island Resort
Enjoy serene lakeside views from the dock, surrounded by lush greenery and rolling hills.

Tea Island Resort

2.0 star property
9.4 out of 10, Exceptional, (190)
"The staff was very friendly . It’s nice they had kayaks and canoes to use. Definitely will go back again"
Tea Island Resort
Lakefront Terrace Resort
Relax by the serene pool surrounded by a deck with lounge chairs and tables, offering a tranquil view of the lake and distant mountains.

Lakefront Terrace Resort

3.0 star property
8.2 out of 10, Very good, (895)
"Great location very nice little beach hotel was clean"
Lakefront Terrace Resort
Inn on the Hill
Relax in a serene outdoor space with a picnic table and comfortable seating, surrounded by lush greenery and a view of the surrounding neighborhood.

Inn on the Hill

2.5 star property
8.8 out of 10, Excellent, (303)
"Love the place, amazing environment, very friendly, they let us check out later then we suppose to very comfortably love it."
Inn on the Hill
Tiki Resort
Experience the unique Tiki hotel, featuring a distinctive triangular roof design and central tiki-inspired structure, with a pool and Polynesian dinner options available.

Tiki Resort

3.0 star property
7.6 out of 10, Good, (1003)
"Peaceful, I love this place "
Tiki Resort
Holiday Inn Resort Lake George - Adirondack Area by IHG
Relax by the fire pit in a cozy outdoor seating area surrounded by Adirondack chairs.

Holiday Inn Resort Lake George - Adirondack Area by IHG

3.0 star property
9.2 out of 10, Wonderful, (1004)
"Great place to stay with the family or for a nice romantic get away. "
The price is €263
includes taxes & fees
17 Aug - 18 Aug
Holiday Inn Resort Lake George - Adirondack Area by IHG
Lake View Inn
Bed sheets

Lake View Inn

2.0 star property
5.6 out of 10, (284)
"I would never stay here again. Floor and ceiling falling apart not even a wash cloth. They should.of paid me to stay there."
The price is €82
includes taxes & fees
22 Jul - 23 Jul
Lake View Inn
Fort William Henry Hotel and Conference Center
Enjoy waterfront views from the pier, where a paddle steamer awaits.

Fort William Henry Hotel and Conference Center

3.0 star property
8.4 out of 10, Very good, (1003)
"Wonderful stay"
The price is €282
includes taxes & fees
4 Aug - 5 Aug
Fort William Henry Hotel and Conference Center
Lake Crest Inn
Experience the rustic charm of this log cabin-style hotel, featuring a welcoming front porch and cozy seating area.

Lake Crest Inn

2.5 star property
8.2 out of 10, Very good, (205)
"great and with a good location"
The price is €170
includes taxes & fees
20 Jul - 21 Jul
Lake Crest Inn
Surfside On The Lake
Enjoy serene lakeside views from the pier, where you can sit and relax on benches and tables.

Surfside On The Lake

2.5 star property
8.0 out of 10, Very good, (621)
"Awesome place "
The price is €216
includes taxes & fees
29 Jul - 30 Jul
Surfside On The Lake
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 Chester Shores Hotel Reviews

Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George

10/10 Excellent
"Love the staff, very friendly and helpful! Pool is great, rooms are clean and it’s right downtown, can walk everywhere..!"
Debra 2-night trip
Posted 12 hours ago
Howard Johnson by Wyndham Lake George

Frequently asked questions

What is Chester Shores like?

Travellers will be sure to enjoy their time in Chestertown's Chester Shores neighbourhood. Consider a visit to Loon Lake as part of your Chester Shores travel plans.

What's a favourite hotel to stay in Chester Shores?

For your stay in Chester Shores, Lakefront Home with WiFi, Dock, Lake Views From the Deck, and Screened-In Porch is one of the top choices based on our traveller data.

How many hotels will I be able to find in the Chester Shores area?

Book one of Expedia's 5 hotels and other accommodation options in Chester Shores and start exploring everything Chestertown has to offer.

If I need to cancel my hotel reservation in Chester Shores, will I receive a refund?

Yes, the majority of hotel room reservations are fully refundable if cancelled prior to the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to review the best deals in Chester Shores.

What are the top things to see and do in Chester Shores?

Loon Lake is an attraction you might want to check out while you're in Chester Shores. While you're out sightseeing in Chestertown, make sure that you visit other sights such as Loon Lake Beach or Friends Lake.