Chester Shores Hotels, Chestertown

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Check prices for these dates

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

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Our top choices for Chester Shores hotels

Private beach, beach volleyball, sailing, kayaking
Silver Bay YMCA Inn and Conference Center

Silver Bay YMCA Inn and Conference Center

Silver Bay YMCA Inn and Conference Center
3.0 star property
27.7 km from Chester Shores
8.8 out of 10, Excellent, (136)
"Awesome place"
United States
Kevin
The price is AU$163
includes taxes & fees
11 Jan - 12 Jan 2026
Silver Bay YMCA Inn and Conference Center
Premium Room
The Alpine Lodge

The Alpine Lodge

The Alpine Lodge
3.0 star property
11.8 km from Chester Shores
9.0 out of 10, Wonderful, (664)
"Nice room, great location, electric vehicle charging was a bonus!"
United States
Tom
The Alpine Lodge
Lake view
The Fern Lodge

The Fern Lodge

The Fern Lodge
3.5 star property
4.3 km from Chester Shores
10.0 out of 10, Exceptional, (51)
"I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning! "
United States
Morgan
The Fern Lodge
Deluxe Cabin
Maple Leaf Motel

Maple Leaf Motel

Maple Leaf Motel
2.5 star property
22.5 km from Chester Shores
8.8 out of 10, Excellent, (549)
"Convenient check in, good value."
United States
Dalei
The price is AU$181
includes taxes & fees
1 Jan - 2 Jan 2026
Maple Leaf Motel
Lunch, dinner served; German cuisine, garden views
Gore Mountain Lodge

Gore Mountain Lodge

Gore Mountain Lodge
2.0 star property
11.7 km from Chester Shores
9.2 out of 10, Wonderful, (212)
"hi, everything was great, would go back again, great location!! "
United States
david
Gore Mountain Lodge
Restaurant
North Creek Lodge at Gore Mountain

North Creek Lodge at Gore Mountain

North Creek Lodge at Gore Mountain
3.0 star property
12.4 km from Chester Shores
8.0 out of 10, Very good, (407)
"Convenient location...Staff was super friendly and the rooms were clean and well put together. Breakfast was nice also. The only thing I could ask for would be nicer pillows."
United States
Peter
The price is AU$236
includes taxes & fees
1 Jan - 2 Jan 2026
North Creek Lodge at Gore Mountain
Front of property
Llama House ADK

Llama House ADK

Llama House ADK
2.5 star property
6.7 km from Chester Shores
9.2 out of 10, Wonderful, (32)
"It was great!"
United States
Elif
The price is AU$229
includes taxes & fees
5 Jan - 6 Jan 2026
Llama House ADK
Luxury Cabin, 1 Bedroom, Lake View | Living area
Trout House Village Resort

Trout House Village Resort

Trout House Village Resort
3.0 star property
29.8 km from Chester Shores
9.8 out of 10, Exceptional, (21)
"Great updated cabin. "
United States
Diane
The price is AU$285
includes taxes & fees
2 Jan - 3 Jan 2026
Trout House Village Resort
Premium Chalet, Multiple Beds | Terrace/patio
Lodge at Schroon Lake

Lodge at Schroon Lake

Lodge at Schroon Lake
3.0 star property
20.2 km from Chester Shores
9.0 out of 10, Wonderful, (416)
"Nice restaurant- welcoming staff, good live music! "
United States
Kathleen
Lodge at Schroon Lake
Interior
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
3.0 star property
18.5 km from Chester Shores
9.8 out of 10, Exceptional, (16)
"Amazing castle! Beautiful views of Lake George. Your own private hidden getaway. The most unique experience in Lake George."
United States
Shannon
The price is AU$2,006
includes taxes & fees
8 Jan - 9 Jan 2026
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
Exterior detail
Lodges At Cresthaven

Lodges At Cresthaven

Lodges At Cresthaven
4.0 star property
26.8 km from Chester Shores
9.4 out of 10, Exceptional, (548)
"Perfect view, great resort"
United States
Melike
The price is AU$270
includes taxes & fees
4 Jan - 5 Jan 2026
Lodges At Cresthaven
Ballroom
Sun Castle Resort

Sun Castle Resort

Sun Castle Resort
3.5 star property
26.9 km from Chester Shores
9.0 out of 10, Wonderful, (62)
"Lovely property the lake is calming and beautiful. "
United States
patricia
The price is AU$508
includes taxes & fees
1 Jan - 2 Jan 2026
Sun Castle Resort
Interior
Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG
3.0 star property
29.8 km from Chester Shores
9.2 out of 10, Wonderful, (1002)
"We enjoyed our stay!"
United States
Audrey
The price is AU$182
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Resort Lake George - Adirondack Area by IHG
Bar (on property)
The Inn of Lake George

The Inn of Lake George

The Inn of Lake George
2.5 star property
28.9 km from Chester Shores
9.6 out of 10, Exceptional, (105)
"We had a great time at the Inn. The owner was super friendly and even left us a baby champagne bottle as it was our wedding anniversary! It was easy to check in and check out and the bar area downstairs is amazing. "
United States
Sanjit
The Inn of Lake George
BBQ/picnic Area
Surfside On The Lake

Surfside On The Lake

Surfside On The Lake
2.5 star property
28.3 km from Chester Shores
8.0 out of 10, Very good, (738)
"Nice property and location. "
United States
robert
Surfside On The Lake
Room, Multiple Beds, Lake View (Balcony)
Courtyard by Marriott Lake George

Courtyard by Marriott Lake George

Courtyard by Marriott Lake George
3.0 star property
28.5 km from Chester Shores
9.2 out of 10, Wonderful, (1001)
"Staff was very courteous and welcoming! Rooms were spacious and clean."
United States
Kimberly
The price is AU$186
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard by Marriott Lake George
Aerial view
Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center
3.0 star property
29.2 km from Chester Shores
8.4 out of 10, Very good, (1001)
"a very nice place to stay"
United States
william
The price is AU$214
includes taxes & fees
12 Jan - 13 Jan 2026
Fort William Henry Hotel and Conference Center
Property amenity
Sundowner on Lake George

Sundowner on Lake George

Sundowner on Lake George
2.5 star property
28.3 km from Chester Shores
7.6 out of 10, Good, (245)
"Great location and friendly staff very clean "
United States
Thomas
The price is AU$253
includes taxes & fees
5 Jan - 6 Jan 2026
Sundowner on Lake George
Property entrance
Lake Haven Motel

Lake Haven Motel

Lake Haven Motel
2.5 star property
28.1 km from Chester Shores
7.4 out of 10, Good, (110)
"For the price this place is totally great! "
United States
Amelia
The price is AU$439
includes taxes & fees
1 Jan - 2 Jan 2026
Lake Haven Motel
House, 3 Bedrooms, Kitchen | Balcony
Pinebrook Motel

Pinebrook Motel

Pinebrook Motel
2.0 star property
28 km from Chester Shores
7.4 out of 10, Good, (186)
"Everything was great, we had a lovely stay and will definitely be back soon!"
United States
Jonathan
The price is AU$112
includes taxes & fees
1 Jan - 2 Jan 2026
Pinebrook Motel
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.
View all properties

Top Chester Shores Hotel Reviews

The Alpine Lodge

The Alpine Lodge

10/10 Excellent
"It was nice and cozy at the Alpine Lodge. Our king bed was very comfortable. The location was good for us; short walk to the Tops grocery store and other little places."
Sherrie 4-night trip
Posted 1 day ago
The Alpine Lodge

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.
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.