Chester Shores Hotels near Chestertown

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Check prices for these dates

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

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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 P5,762
P6,395 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Silver Bay YMCA Inn and Conference Center
Premium bedding, down comforters, 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, (662)
"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
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, (548)
"Convenient check in, good value."
United States
Dalei
The price is P6,290
P7,108 total
includes taxes & fees
Dec 27 - Dec 28
Maple Leaf Motel
Lake view
The Fern Lodge

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
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, (403)
"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 P8,349
P9,267 total
includes taxes & fees
Jan 1 - Jan 2, 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 P8,543
P9,483 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Llama House ADK
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, (20)
"Great updated cabin. "
United States
Diane
The price is P8,787
P11,222 total
includes taxes & fees
Jan 5 - Jan 6, 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 P63,078
P87,293 total
includes taxes & fees
Jan 6 - Jan 7, 2026
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
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 P9,574
P10,627 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Lodges At Cresthaven
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, (415)
"Nice restaurant- welcoming staff, good live music! "
United States
Kathleen
Lodge at Schroon Lake
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 P14,025
P19,972 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Sun Castle Resort
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
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, (1001)
"We enjoyed our stay!"
United States
Audrey
The price is P6,461
P7,171 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Holiday Inn Resort Lake George - Adirondack Area by IHG
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
Premium bedding, desk, laptop workspace, blackout drapes
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)
"Loved my stay, the room was comfy and nice and clean, plenty to do right in the hotel"
United States
Debbie
The price is P6,578
P7,302 total
includes taxes & fees
Jan 5 - Jan 6, 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 P7,100
P8,999 total
includes taxes & fees
Jan 1 - Jan 2, 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 P4,567
P9,959 total
includes taxes & fees
Jan 12 - Jan 13, 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 P12,371
P18,622 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Lake Haven Motel
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 P3,951
P4,386 total
includes taxes & fees
Dec 28 - Dec 29
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

Super 8 by Wyndham Lake George/Warrensburg Area

Super 8 by Wyndham Lake George/Warrensburg Area

10/10 Excellent
"The front desk for morning is very nice. "
Doaa 1-night trip
Posted 2 days ago
Super 8 by Wyndham Lake George/Warrensburg Area

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.
How many hotels will I find in the Chester Shores area?
Book one of Expedia's 5 hotels and other accommodations 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! 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.
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.

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