Hotels in Chester Shores

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Check prices for these dates

Tonight
Sep 19 - Sep 20
Tomorrow
Sep 20 - Sep 21
This weekend
Sep 19 - Sep 21
Next weekend
Sep 26 - Sep 28

Where to stay in Chester Shores?

Chester Shores hotels that make comfort easy

Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (140)
$175 nightly
The price is $194
Sep 21 - Sep 22
Total with taxes and fees
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 October

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 September
Currently viewing crowd sizes and weather for September.
Weather forecast for Chestertown
September
trending_flatModerate crowds
High 71°F / low 51°F. Sunny most days.
View properties in September
71°
weather_sun
September, Moderate crowds, average high temperature 71 degrees Fahrenheit, average low temperature 51 degrees Fahrenheit. Sunny most days.
51°
57°
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October, High crowds, average high temperature 57 degrees Fahrenheit, average low temperature 41 degrees Fahrenheit. Cloudy most days.
41°
44°
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November, Low crowds, average high temperature 44 degrees Fahrenheit, average low temperature 29 degrees Fahrenheit. Partly sunny.
29°
33°
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December, Moderate crowds, average high temperature 33 degrees Fahrenheit, average low temperature 22 degrees Fahrenheit. Snow likely.
22°
28°
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January, Low crowds, average high temperature 28 degrees Fahrenheit, average low temperature 13 degrees Fahrenheit. Snow likely.
13°
30°
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February, Moderate crowds, average high temperature 30 degrees Fahrenheit, average low temperature 14 degrees Fahrenheit. Snow likely.
14°
39°
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March, Low crowds, average high temperature 39 degrees Fahrenheit, average low temperature 22 degrees Fahrenheit. Snow likely.
22°
52°
weather_cloudy
April, Moderate crowds, average high temperature 52 degrees Fahrenheit, average low temperature 33 degrees Fahrenheit. Cloudy most days.
33°
67°
weather_sun
May, Low crowds, average high temperature 67 degrees Fahrenheit, average low temperature 45 degrees Fahrenheit. Sunny most days.
45°
74°
weather_sun
June, High crowds, average high temperature 74 degrees Fahrenheit, average low temperature 53 degrees Fahrenheit. Sunny most days.
53°
80°
weather_sun
July, High crowds, average high temperature 80 degrees Fahrenheit, average low temperature 59 degrees Fahrenheit. Sunny most days.
59°
78°
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August, High crowds, average high temperature 78 degrees Fahrenheit, average low temperature 58 degrees Fahrenheit. Sunny most days.
58°
Monthly weather averages (˚F)

Top landmarks in Chestertown

Friends Lake

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
Loon Lake

Loon Lake

Loon Lake is 3.2 mi (5.2 km) from central Chestertown, why not stop by during your stay.

See properties in Loon Lake

Check out reviews of Chester Shores hotels guests love

Courtyard by Marriott Lake George

Courtyard by Marriott Lake George

10/10 Excellent
"Great views "
Richard 1-night trip
Posted 20 hours ago
Courtyard by Marriott Lake George

Frequently asked questions

Is Chester Shores expensive to stay in?
You can find great hotels from $74 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.
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".
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.

Find out more about Chester Shores

Find out more about Chester Shores

What's Chester Shores Like?

If you're in search of the perfect part of town to visit, why not check out Chester Shores? Take time to see the sights like Loon Lake while you're here. Loon Lake Beach and Friends Lake are a couple of more places to see nearby.

How to Get to Chester Shores

Flying to:

  • Glens Falls, NY (GFL-Floyd Bennett Memorial), 25.4 mi (40.9 km) from Chester Shores

Things to See and Do in and around Chester Shores

Things to See near Chester Shores:

  • Loon Lake (1 mi/1.7 km away)
  • Loon Lake Beach (0.4 mi/0.7 km away)
  • Friends Lake (2.6 mi/4.3 km away)

When Is the Best Time to Visit Chestertown?

  • Hottest months: July, August, June, September (average 65°F)
  • Coldest months: January, February, March, December (average 25°F)
  • Rainiest months: June, July, October, August (average 5 inches of rainfall)

Chester Shores Travel Information

Best Time to Visit
January, July and August
Average Stay
2 days
Closest Neighborhoods
Upper Tahawus Glades, Sagamore Glades
Top Attractions
Friends Lake, Loon Lake, Loon Lake Beach

Keep exploring

Keep exploring