Search Hotels in Chester Shores, Chestertown

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
28 Dec - 29 Dec
Tomorrow
29 Dec - 30 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Filter by

Guest rating
Guest rating
Star rating

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 Rp1.642.684
Rp1.823.381 total
includes taxes & fees
11 Jan - 12 Jan 2026
Silver Bay YMCA Inn and Conference Center
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, (406)
"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 Rp2.380.386
Rp2.642.229 total
includes taxes & fees
1 Jan - 2 Jan 2026
North Creek Lodge at Gore Mountain
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 price is Rp10.029.418
Rp11.132.746 total
includes taxes & fees
14 Jan - 15 Jan 2026
The Fern Lodge
Premium Room | Premium bedding, down duvets, individually decorated
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, (663)
"Nice room, great location, electric vehicle charging was a bonus!"
United States
Tom
The Alpine Lodge
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
Deluxe Cabin | Individually decorated, individually furnished, laptop workspace
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 Rp1.793.390
Rp2.026.480 total
includes taxes & fees
30 Dec - 31 Dec
Maple Leaf Motel
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 Rp2.435.719
Rp2.703.649 total
includes taxes & fees
31 Dec - 1 Jan 2026
Llama House ADK
Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services
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, (20)
"Great updated cabin. "
United States
Diane
The price is Rp2.505.320
Rp3.199.529 total
includes taxes & fees
4 Jan - 5 Jan 2026
Trout House Village Resort
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 Rp17.984.130
Rp24.887.926 total
includes taxes & fees
4 Jan - 5 Jan 2026
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
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 Rp3.998.706
Rp5.694.305 total
includes taxes & fees
1 Jan - 2 Jan 2026
Sun Castle 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
Exterior
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 Rp2.729.720
Rp3.029.988 total
includes taxes & fees
4 Jan - 5 Jan 2026
Lodges At Cresthaven
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
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 Rp1.957.133
Rp3.566.438 total
includes taxes & fees
30 Dec - 31 Dec
Lake Haven Motel
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 Rp1.302.060
Rp2.839.309 total
includes taxes & fees
12 Jan - 13 Jan 2026
Sundowner on 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
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 Rp1.841.950
Rp2.044.564 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Resort Lake George - Adirondack Area by IHG
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 Rp1.126.604
Rp1.250.517 total
includes taxes & fees
30 Dec - 31 Dec
Pinebrook Motel
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 Rp2.020.954
Rp2.561.483 total
includes taxes & fees
12 Jan - 13 Jan 2026
Fort William Henry Hotel and Conference Center
Room, Multiple Beds, Lake View (Balcony) | Premium bedding, desk, laptop workspace, blackout curtains
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, (1003)
"Loved my stay, the room was comfy and nice and clean, plenty to do right in the hotel"
United States
Debbie
The price is Rp1.875.440
Rp2.081.738 total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard by Marriott Lake George
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
"Motel but Room itself is nicely decorated, new, clean, and bed is cozy. No closet but there are hangers, hooks, and a luggage cot. Parking is limited but just right. Shared Lodge is a nice touch with microwave, fridge, and other facilities. Would like a person for concierge. Food and grocery market walkable distance. Would stay here again!"
Victoria 1-night trip
Posted 3 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.