Chestertown Hotel Guide. Hotels in Chester Shores, Chestertown, United States of America

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
29 Aug - 31 Aug
Next weekend
5 Sept - 7 Sept

Filter by

Guest rating
Guest rating
Property class

Top Trending Hotels Near Chester Shores, Chestertown

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

Silver Bay YMCA Inn and Conference Center

3.0 star property
8.8 out of 10, Excellent, (109)
"Great beach and room. "
The price is €99
includes taxes & fees
4 Sept - 5 Sept
Silver Bay YMCA Inn and Conference Center
Trout House Village Resort
Luxury Cabin, 1 Bedroom, Lake View | Living area

Trout House Village Resort

3.0 star property
9.8 out of 10, Exceptional, (12)
"Absolutely wonderful place and super friendly staff "
The price is €158
includes taxes & fees
2 Sept - 3 Sept
Trout House Village Resort
Doray Motel
Property grounds

Doray Motel

2.0 star property
8.4 out of 10, Very good, (178)
"Very cute and clean rooms, staff was incredibly kind and friendly!"
The price is €62
includes taxes & fees
8 Sept - 9 Sept
Doray Motel
Sundowner on Lake George
Property amenity

Sundowner on Lake George

2.5 star property
7.4 out of 10, Good, (242)
"Looks completely renovated. Directly on Lake George. Free kayaks. Short walking distance to the town."
The price is €140
includes taxes & fees
1 Sept - 2 Sept
Sundowner on Lake George
Seven Dwarfs Motel and Cabins
Seasonal outdoor pool

Seven Dwarfs Motel and Cabins

2.0 star property
7.4 out of 10, Good, (163)
"Owners and staff were extremely accommodating and friendly"
The price is €75
includes taxes & fees
8 Sept - 9 Sept
Seven Dwarfs Motel and Cabins
Pinebrook Motel
House, 3 Bedrooms, Kitchen | Balcony

Pinebrook Motel

2.0 star property
7.4 out of 10, Good, (178)
"Everything was great, we had a lovely stay and will definitely be back soon!"
The price is €54
includes taxes & fees
8 Sept - 9 Sept
Pinebrook Motel
Windsor Motel
Restaurant

Windsor Motel

2.5 star property
7.4 out of 10, Good, (222)
"Nice staff and convenient location. Good price. Clean and comfortable."
The price is €52
includes taxes & fees
8 Sept - 9 Sept
Windsor Motel
Depe Dene Lakeside Resort
Historic Mansion with Lakeview

Depe Dene Lakeside Resort

2.0 star property
8.8 out of 10, Excellent, (344)
"Wonderful - nice stay and very clean. "
Depe Dene Lakeside Resort
Fran Cove Motel
BBQ/picnic Area

Fran Cove Motel

2.0 star property
7.8 out of 10, Good, (313)
"quiet place "
The price is €77
includes taxes & fees
8 Sept - 9 Sept
Fran Cove Motel
Barberry Court Motel
Terrace/patio

Barberry Court Motel

2.5 star property
7.2 out of 10, Good, (104)
"Enjoyed our stay"
The price is €81
includes taxes & fees
12 Sept - 13 Sept
Barberry Court Motel
The Juliana Resort
Terrace/patio

The Juliana Resort

2.5 star property
8.8 out of 10, Excellent, (171)
"Such a cute little resort. Perfect for a family."
The price is €122
includes taxes & fees
8 Sept - 9 Sept
The Juliana Resort
Tiki Resort
Front of property – evening/night

Tiki Resort

3.0 star property
7.6 out of 10, Good, (1010)
"I love this hotel walking distance to everything, staff very friendly"
Tiki Resort
Amber Lantern Lake George Motel and Cottage Rentals
Exterior

Amber Lantern Lake George Motel and Cottage Rentals

2.0 star property
8.4 out of 10, Very good, (299)
"Nice place in a very convenient location"
The price is €81
includes taxes & fees
9 Sept - 10 Sept
Amber Lantern Lake George Motel and Cottage Rentals
Brookside Motel
Outdoor pool, pool loungers

Brookside Motel

2.5 star property
8.6 out of 10, Excellent, (643)
"Nice place friendly people."
The price is €70
includes taxes & fees
8 Sept - 9 Sept
Brookside Motel
Lake Haven Motel
Property entrance

Lake Haven Motel

2.5 star property
7.4 out of 10, Good, (109)
"Motel in lake George. Exactly as advertised, exactly how I expected it. I was the only vehicle in the lot. Season hasn't started yet. But seems like a nice place for all. I would stay again"
Lake Haven Motel
Boulder's Resort
Front of property

Boulder's Resort

2.0 star property
8.6 out of 10, Excellent, (40)
"We go to lake George annually, this was the first time at this resort. We absolutely loved it and will be returning again. Highly recommended wonderful resort."
The price is €176
includes taxes & fees
8 Sept - 9 Sept
Boulder's Resort
Lincoln Log Colony
Fireplace

Lincoln Log Colony

2.0 star property
8.8 out of 10, Excellent, (3)
"This is a great property. Initially we rented a large “suite” but immediately upgraded to one of their adorable cabins just across from the playground and pool. The property has super nice and accommodating staff, plenty of parking and really nice families staying there; some are regulars for 20, 40 years! This is truly a family stay place and we were so happy to have found it. Now we’re planning to return year after year! Two beautiful Adirondack chairs on a quiet little stoop outside of each...
The price is €121
includes taxes & fees
8 Sept - 9 Sept
Lincoln Log Colony
Lido Motel Lake George
Outdoor dining

Lido Motel Lake George

2.0 star property
7.6 out of 10, Good, (231)
"It was a cute motel. I would definitely stay hwre again. Easy check in. Peaceful and quiet. Within walking distance of a lot to do. "
The price is €65
includes taxes & fees
8 Sept - 9 Sept
Lido Motel Lake George
The Lake George Inn
1 bedroom, iron/ironing board, free WiFi

The Lake George Inn

2.0 star property
5.0 out of 10, (2)
"I would not recommend this property!"
The Lake George Inn
Park Lane Motel
Terrace/patio

Park Lane Motel

2.5 star property
8.8 out of 10, Excellent, (257)
"Great location, pool, clean rooms. A great motel. "
The price is €94
includes taxes & fees
1 Sept - 2 Sept
Park Lane 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Shores Hotel Reviews

Americas Best Value Inn & Suites Lake George

Americas Best Value Inn & Suites Lake George

10/10 Excellent
"Overall great experience. Check in was easy, and check out. Adrianna from front desk was very helpful! I would recommend to families. Clean, and walk distant to everything "
Leticia 2-night trip
Posted 1 day ago
Americas Best Value Inn & Suites Lake George

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.