Chester Shores Hotels, Chestertown

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Check prices for these dates

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

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1149 Cheap Hotels in Chester Shores - Specials, Reviews, & Last Minute Deals

Aerial view
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, (1003)
"Clean room great customer service and the grounds were great for the Lake"
United States
ROBERT
The price is AU$243
includes taxes & fees
16 Dec - 17 Dec
Fort William Henry Hotel and Conference Center
Exterior
Lodges At Cresthaven

Lodges At Cresthaven

4.0 star property
26.8 km from Chester Shores
9.4 out of 10, Exceptional, (542)
"Perfect view, great resort"
United States
Melike
The price is AU$273
includes taxes & fees
21 Dec - 22 Dec
Lodges At Cresthaven
Exterior
Super 8 by Wyndham Lake George/Warrensburg Area

Super 8 by Wyndham Lake George/Warrensburg Area

2.5 star property
21 km from Chester Shores
8.6 out of 10, Excellent, (1001)
"Great staff. Great value."
United States
Darkhan
The price is AU$119
includes taxes & fees
15 Dec - 16 Dec
Super 8 by Wyndham Lake George/Warrensburg Area
Room, Multiple Beds, Lake View (Balcony)
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, (1005)
"Loved my stay, the room was comfy and nice and clean, plenty to do right in the hotel"
United States
Debbie
The price is AU$194
includes taxes & fees
11 Dec - 12 Dec
Courtyard by Marriott Lake George
Interior
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, (1001)
"We enjoyed our stay!"
United States
Audrey
The price is AU$184
includes taxes & fees
10 Dec - 11 Dec
Holiday Inn Resort Lake George - Adirondack Area by IHG
Premium Room
The Alpine Lodge

The Alpine Lodge

3.0 star property
11.8 km from Chester Shores
9.0 out of 10, Wonderful, (657)
"As described, clean, good location. "
United States
Julianne
The Alpine Lodge
Premium Chalet, Multiple Beds | Terrace/patio
Lodge at Schroon Lake

Lodge at Schroon Lake

3.0 star property
20.2 km from Chester Shores
9.0 out of 10, Wonderful, (414)
"Nice restaurant- welcoming staff, good live music! "
United States
Kathleen
Lodge at Schroon Lake
Luxury Cabin, 1 Bedroom, Lake View | Living area
Trout House Village Resort

Trout House Village Resort

3.0 star property
29.8 km from Chester Shores
9.8 out of 10, Exceptional, (18)
"Very friendly owner and beautiful views"
United States
Anthony
The price is AU$288
includes taxes & fees
9 Dec - 10 Dec
Trout House Village Resort
Private beach, beach volleyball, sailing, kayaking
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$147
includes taxes & fees
9 Dec - 10 Dec
Silver Bay YMCA Inn and Conference Center
Property amenity
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)
"Pool was closed (off season)."
United States
John
The price is AU$304
includes taxes & fees
5 Jan - 6 Jan 2026
Sundowner on Lake George
BBQ/picnic Area
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
House, 3 Bedrooms, Kitchen | Balcony
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
9 Dec - 10 Dec
Pinebrook Motel
Lunch, dinner served; German cuisine, garden views
Gore Mountain Lodge

Gore Mountain Lodge

2.0 star property
11.7 km from Chester Shores
9.2 out of 10, Wonderful, (211)
"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

3.0 star property
12.4 km from Chester Shores
8.0 out of 10, Very good, (402)
"Mattresses were incredibly comfortable, room felt clean. Only thing we did not like was that there was not a deadbolt on the door. "
United States
John
The price is AU$202
includes taxes & fees
9 Dec - 10 Dec
North Creek Lodge at Gore Mountain
Bar (on property)
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
Property entrance
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$216
includes taxes & fees
11 Dec - 12 Dec
Lake Haven Motel
Lake view
The Fern Lodge

The Fern Lodge

3.5 star property
4.3 km from Chester Shores
9.8 out of 10, Exceptional, (50)
"Absolutely beautiful "
United States
Dana
The Fern Lodge
Interior
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$2,113
includes taxes & fees
16 Dec - 17 Dec
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
Ballroom
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$593
includes taxes & fees
9 Dec - 10 Dec
Sun Castle Resort
Deluxe Cabin
Maple Leaf Motel

Maple Leaf Motel

2.5 star property
22.5 km from Chester Shores
8.8 out of 10, Excellent, (547)
"This was a great place with nice amenities and a comfortable bed. "
United States
Elizabeth
The price is AU$182
includes taxes & fees
9 Dec - 10 Dec
Maple Leaf 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.
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Top Chester Shores Hotel Reviews

The Alpine Lodge

The Alpine Lodge

10/10 Excellent
"Clean and easy to check in and out "
dohee 3-night trip
Posted 6 days 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.