Hotels in Chester Shores

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Check prices for these dates

Tonight
Jul 27 - Jul 28
Tomorrow
Jul 28 - Jul 29
Next weekend
Aug 1 - Aug 3
In two weeks
Aug 8 - Aug 10

Where to stay in Chester Shores?

Pine Tree Motel & Cabins
Cabins with front porches and lawns set amidst dense coniferous trees.

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (130)
The price is $175
$194 total
includes taxes & fees
Jul 28 - Jul 29
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 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
View properties in July

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Currently viewing crowd sizes and weather for July.
Weather forecast for Chestertown
July
trending_upHigh crowds
High 27°C / low 15°C. Sunny most days.
View properties in July
27°
weather_sun
July, High crowds, average high temperature 27 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
26°
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August, High crowds, average high temperature 26 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
22°
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September, Moderate crowds, average high temperature 22 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
14°
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October, High crowds, average high temperature 14 degrees Celsius, average low temperature 5 degrees Celsius. Cloudy most days.
5°
7°
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November, Low crowds, average high temperature 7 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
-1°
1°
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December, Moderate crowds, average high temperature 1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
-2°
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January, Low crowds, average high temperature -2 degrees Celsius, average low temperature -11 degrees Celsius. Snow likely.
-11°
-1°
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February, Moderate crowds, average high temperature -1 degrees Celsius, average low temperature -10 degrees Celsius. Snow likely.
-10°
4°
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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°
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June, High crowds, average high temperature 23 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
12°
Monthly weather averages (˚C)

Top landmarks in Chestertown

Friends Lake

Friends Lake

5/5(3 reviews)

Friends Lake is 2.8 mi (4.5 km) from central Chestertown, why not stop by during your stay. Chestertown has other popular natural features you might want to visit such as Lake George.

See properties in Friends Lake
Loon Lake Beach

Loon Lake Beach

If you can't wait to get to the beach, you might enjoy a trip to Loon Lake Beach located 2 mi (3.3 km) from central Chestertown. Chestertown has other popular natural features you might want to visit such as Lake George.

See properties in Loon Lake Beach

Check out reviews of Chester Shores hotels guests love

Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

10/10 Excellent
"Great stay!"
Kristina 4-night trip
Posted 1 day ago
Fort William Henry Hotel and Conference Center

Frequently asked questions

Is Chester Shores expensive to stay in?
You can find great hotels from $64 in Chester Shores to suit a range of budgets. To find the best low-cost hotel on Hotels.com that meets your needs, apply your search filters and then sort hotels by "Price: low to high".
How can I find discounted rates and deals for Chester Shores hotels?
Unlocking discounted rates at hotels in Chester Shores couldn't be simpler. Members save up to 20% on select hotels when signed in. Silver, Gold, and Platinum members can earn additional rewards on VIP Access bookings.
How can I find discounted rates and deals for Chester Shores hotels?
Discover great deals on hotels in Chester Shores with Hotels.com. Sign up for free to unlock member only prices and start earning rewards. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Chester Shores hotels.
Can I receive a refund if I cancel my Chester Shores hotel booking?
The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel your booking. Some Chester Shores hotels require you to cancel more than 24 hours before check-in, so look at your booking beforehand. For extra peace of mind before you book, filter hotels by "Property cancellation options" and select "Fully refundable property".
What are some of the best pet-friendly hotels in Chester Shores?
Traveling with your pet doesn't mean sacrificing a great hotel stay. In Chester Shores, our travelers love:To find more pet-friendly stays on Hotels.com, use the "Amenities" filter in your search and select "Pet friendly".
What are some of the best Chester Shores hotels with a pool?
Book a Chester Shores hotel with a pool for some added relaxation or exercise on your trip. For more Chester Shores hotels with a pool, use the "Amenities" filter in your search and select "Pool" on Hotels.com.
What are some great hotels in Chester Shores with balconies?
There are some top hotels in Chester Shores that offer rooms with a balcony.
Are all taxes and fees included in the Chester Shores hotel prices shown on Hotels.com?
Hotels.com provides upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.