Chester Shores Hotels near Chestertown

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near Chester Shores, Chestertown

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
Exterior
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
3.0 star property
9.6 out of 10, Exceptional, (14)
"John and Yvonne were the perfect hosts hosts...Tvicolorfulsunse"
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
Lodge at Schroon Lake
Terrace/patio
Lodge at Schroon Lake
3.0 star property
8.8 out of 10, Excellent, (262)
"Everyone on the staff is helpful and friendly. The property is conveniently located and easy to find. It's not your typical hotel but well worth checking out. Kid and dog friendly too!"
The price is P5,733
P7,944 total
includes taxes & fees
Nov 24 - Nov 25
Lodge at Schroon Lake
Super 8 by Wyndham Ticonderoga
Exterior
Super 8 by Wyndham Ticonderoga
2.5 star property
7.8 out of 10, Good, (984)
"Very pleased with the accommodations"
The price is P4,508
P5,094 total
includes taxes & fees
Dec 2 - Dec 3
Super 8 by Wyndham Ticonderoga
Best Western Plus Ticonderoga Inn & Suites
Exterior
Best Western Plus Ticonderoga Inn & Suites
2.5 star property
8.6 out of 10, Excellent, (662)
"Enjoyed our stay but the breakfast food that was to be hot -was cold! "
The price is P7,012
P7,924 total
includes taxes & fees
Nov 25 - Nov 26
Best Western Plus Ticonderoga Inn & Suites
Circle Court Motel
Free WiFi, bed sheets
Circle Court Motel
2.5 star property
8.6 out of 10, Excellent, (265)
"It was exactly as expected"
Circle Court Motel
Trout House Village Resort
Living area
Trout House Village Resort
3.0 star property
10.0 out of 10, Exceptional, (1)
"This one checked all the boxes. The location was great. The cabin was clean, spacious, and nicely decorated in Adirondack style. There were many activities available on the grounds at no extra charge. They even had the fireplace in front of our cabin stacked and ready to light. "
The price is P8,436
P10,837 total
includes taxes & fees
Nov 22 - Nov 23
Trout House Village Resort
Maple Leaf Motel
Individually decorated, individually furnished, laptop workspace
Maple Leaf Motel
2.5 star property
8.6 out of 10, Excellent, (404)
"The stay, for the most part was comfortable. As previously mentioned, we could have used a second chair. Housekeeping did not leave any coffee for the second day and the coffee cups were not cleaned. I know budgets are tight but it would have nice to have had plastic cups, tissues and paper towels incase of spills"
The price is P5,781
P6,532 total
includes taxes & fees
Dec 5 - Dec 6
Maple Leaf Motel
Boathouse Waterfront Lodging
Front of property - evening/night
Boathouse Waterfront Lodging
3.5 star property
9.4 out of 10, Exceptional, (19)
"The best place to stay, hands down in Bolton and Lake George. I have been many times and cannot wait until next year!!"
Boathouse Waterfront Lodging
Pine Tree Motel & Cabins
Exterior
Pine Tree Motel & Cabins
2.0 star property
9.2 out of 10, Wonderful, (126)
"very friendly and helpful owners. rooms were very clean and comfortable. good location as well"
Pine Tree Motel & Cabins
Chateau Rooms
Lake view
Chateau Rooms
4.5 star property
9.0 out of 10, Wonderful, (49)
"Cozy, private and quiet was just what we needed. Warm and comfortable bed. Close to boat rental and hiking. "
Chateau Rooms
Friends Lake Inn
1 bedroom, premium bedding, individually decorated
Friends Lake Inn
4.0 star property
8.8 out of 10, Excellent, (83)
"Great room, very nice staff. Nice weekend getaway."
The price is P8,970
P9,957 total
includes taxes & fees
Nov 22 - Nov 23
Friends Lake Inn
The Fern Lodge
Lake view
The Fern Lodge
3.5 star property
9.8 out of 10, Exceptional, (45)
"We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer."
The price is P27,319
P30,324 total
includes taxes & fees
Nov 24 - Nov 25
The Fern Lodge
Silver Bay YMCA Inn and Conference Center
Front of property
Silver Bay YMCA Inn and Conference Center
3.0 star property
8.4 out of 10, Very Good, (84)
"This was a great surprise. What a beautiful place."
The price is P5,764
P6,398 total
includes taxes & fees
Nov 25 - Nov 26
Silver Bay YMCA Inn and Conference Center
Cabin w/ Beach Access in Brant Lake: Dogs Welcome!
Beach
Cabin w/ Beach Access in Brant Lake: Dogs Welcome!
3.0 star property
Cabin w/ Beach Access in Brant Lake: Dogs Welcome!
Peaceful Brant Lake Home < 1 Mi to Beach!
Private kitchen
Peaceful Brant Lake Home < 1 Mi to Beach!
3.0 star property
10.0 out of 10, Exceptional, (3)
"House is amazing and roomy"
Peaceful Brant Lake Home < 1 Mi to Beach!
Tree Tops Retreat ~ 19 Mi to Lake George!
Interior
Tree Tops Retreat ~ 19 Mi to Lake George!
3.0 star property
Tree Tops Retreat ~ 19 Mi to Lake George!
Updated Bolton Home w/ Fire Pit!
Terrace/patio
Updated Bolton Home w/ Fire Pit!
3.0 star property
Updated Bolton Home w/ Fire Pit!
Waterfront Lake George Lodge w/ Boat Dock & Lift!
Marina
Waterfront Lake George Lodge w/ Boat Dock & Lift!
3.0 star property
Waterfront Lake George Lodge w/ Boat Dock & Lift!
Pet-friendly Bolton Vacation Rental w/ Game Room!
TV
Pet-friendly Bolton Vacation Rental w/ Game Room!
3.0 star property
Pet-friendly Bolton Vacation Rental w/ Game Room!
Chestertown Hideaway w/ Lake & Beach Access!
Property grounds
Chestertown Hideaway w/ Lake & Beach Access!
3.0 star property
Chestertown Hideaway w/ Lake & Beach Access!
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.
Don't see what you're looking for?
See all available properties in Chester Shores
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

What is Chester Shores like?

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

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

Yes! You'll find that most hotel room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of check in. If you have a reservation that's non-refundable, you might be able to still cancel and receive a refund within 24 hours of booking. Enter your dates, click on "Search", then filter by "fully refundable" to view top deals in Chester Shores.

Where can I learn more about changing or cancelling my trip to Chester Shores?

For additional details about picking new dates or cancelling your trip to Chester Shores, click here.

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, be sure to visit other sights like Loon Lake Beach or Friends Lake.