Photo by Julie Miller

Hotels in Chestertown

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Check prices for these dates

Tonight
Jul 6 - Jul 7
Tomorrow
Jul 7 - Jul 8
Next weekend
Jul 11 - Jul 13
In two weeks
Jul 18 - Jul 20

Where to stay in Chestertown?

Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (127)
The price is CA $238
CA $264 total
includes taxes & fees
Jul 7 - Jul 8
Pine Tree Motel & Cabins
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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Our prices for hotels in Chestertown are cheapest in July

See average prices and weather for all months

Price trends for hotels in Chestertown

Pricing is based on two traveller single night rates
Jul
CA $437
Average price during July is CA $437
Aug
CA $592
Average price during August is CA $592
Sep
CA $581
Average price during September is CA $581
Oct
CA $487
Average price during October is CA $487
Nov
CA $573
Average price during November is CA $573
Dec
CA $665
Average price during December is CA $665
Jan
CA $688
Average price during January is CA $688
Feb
CA $740
Average price during February is CA $740
Mar
CA $737
Average price during March is CA $737
Apr
CA $723
Average price during April is CA $723
May
CA $710
Average price during May is CA $710
Jun
CA $696
Average price during June is CA $696
Currently viewing crowd sizes and weather for July.

July

trending_upHigh crowds
High 27°C / low 15°C. Sunny most days.
27°
weather_sun
July, High crowds, average high temperature 27 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
26°
weather_sun
August, High crowds, average high temperature 26 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
22°
weather_sun
September, Moderate crowds, average high temperature 22 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
14°
weather_cloudy
October, High crowds, average high temperature 14 degrees Celsius, average low temperature 5 degrees Celsius. Cloudy most days.
5°
7°
weather_partly_sunny
November, Low crowds, average high temperature 7 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
-1°
1°
ac_unit
December, Moderate crowds, average high temperature 1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
-2°
ac_unit
January, Low crowds, average high temperature -2 degrees Celsius, average low temperature -11 degrees Celsius. Snow likely.
-11°
-1°
ac_unit
February, Moderate crowds, average high temperature -1 degrees Celsius, average low temperature -10 degrees Celsius. Snow likely.
-10°
4°
ac_unit
March, Low crowds, average high temperature 4 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
11°
weather_cloudy
April, Moderate crowds, average high temperature 11 degrees Celsius, average low temperature 1 degrees Celsius. Cloudy most days.
1°
19°
weather_sun
May, Low crowds, average high temperature 19 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
7°
23°
weather_sun
June, High crowds, average high temperature 23 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
12°
Monthly weather averages (˚C)
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Top neighborhoods in Chestertown

Chester Shores map

Chester Shores

Chestertown's Chester Shores neighborhood offers attractions including Loon Lake.

Top landmarks in Chestertown

Friends Lake

Commune with nature and explore the great outdoors at Friends Lake during your travels in Chestertown. While you're in the area, stroll along the lakeside.

See properties in Friends Lake
Friends Lake

Learn more about Chestertown

Chestertown is well-known for its attractions such as Loon Lake Beach and Friends Lake. The city has something for everyone including sights like Loon Lake and Hudson River within a secluded setting.

See all hotels in Chestertown
Photo by Julie Miller
Open Photo by Julie Miller

Check out the Chestertown hotels guests love right now

La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent
"Quick 1 night stay in Lake George to break up our trip. The kids loved the hotel, as the pool area had a nice water slide and kiddie pool area. Would definitely stay again!"
Mark 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Lake George

Frequently asked questions

Where can I find free parking with my stay in Chestertown?
Park your car for free at The Loft at The Remington.
Can I book a refundable accommodation in Chestertown?
If you want the flexibility to change your plans to Chestertown, most hotels offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay with my pet in Chestertown?
Your furry friend can stay with you at these pet-friendly hotels: Pine Tree Motel & Cabins, Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing and Three Bears, Immaculate 2 Bed/2.5 bath suite, Heat/ AC & Washer/dryer.
Where can I stay in Chestertown if I want a vacation home instead of a hotel?
If you're looking for a good alternative to a hotel, look over our selection of 61 vacation homes. In addition, there are 8 apartments and 7 condos.
Where can I stay if I'm traveling to Chestertown with my kids?
Parents traveling with children may want to consider Three Bears, Immaculate 2 Bed/2.5 bath suite, Heat/ AC & Washer/dryer.
Where should I stay in Chestertown for a vacation with my partner?
Friends Lake Inn and The Fern Lodge are great options for a romantic getaway.
Where should I stay in Chestertown if I want a luxury hotel?
An option for a luxury stay is Friends Lake Inn.
What will the weather in Chestertown be like during my visit?
The warmest months in Chestertown are usually July and August with an average temp of 65°F. January and February are the chilliest months when the average temp is 25°F. The rainiest months are June and July.
Why should I book my Chestertown hotel with Hotels.com?
There are plenty of reasons to book your Chestertown travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.