Photo by Julie Miller

Hotels in Chestertown

Free cancellation options if plans change
Earn rewards on every night you stay
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Check prices for these dates

Tonight
May 18 - May 19
Tomorrow
May 19 - May 20
Next weekend
May 23 - May 25
In two weeks
May 30 - Jun 1

Where to stay in Chestertown?

Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (126)
The price is P9,738
P10,809 total
includes taxes & fees
May 20 - May 21
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.
trending_down

Our prices for hotels in Chestertown are cheapest in September

See average prices and weather for all months

Price trends for hotels in Chestertown

Pricing is based on two traveler single night rates
May
P 19,948
Average price during May is P 19,948
Jun
P 24,228
Average price during June is P 24,228
Jul
P 27,368
Average price during July is P 27,368
Aug
P 21,110
Average price during August is P 21,110
Sep
P 17,825
Average price during September is P 17,825
Oct
P 24,841
Average price during October is P 24,841
Nov
P 25,089
Average price during November is P 25,089
Dec
P 20,504
Average price during December is P 20,504
Jan
P 27,005
Average price during January is P 27,005
Feb
P 31,147
Average price during February is P 31,147
Mar
P 26,827
Average price during March is P 26,827
Apr
P 21,652
Average price during April is P 21,652
Currently viewing crowd sizes and weather for May.

May

trending_downLow crowds
High 19°C / low 7°C. Sunny most days.
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°
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°
Monthly weather averages (˚C)
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Top landmarks in Chestertown

Friends Lake

Friends Lake is 2.8 mi (4.5 km) from central Chestertown, why not stop by during your stay.

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

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 6 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.