Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Check availability on Chestertown Beach Hotels

This weekend
Jun 26 - Jun 28
Next weekend
Jul 3 - Jul 5

Our top choices for Chestertown beach hotels

Premier Room | 1 bedroom, premium bedding, individually decorated

Friends Lake Inn

Friends Lake Inn
4.0 star property
Chestertown
8.8 out of 10, Excellent, (107 reviews)
The price is ￥36,371
￥40,373 total
includes taxes & fees
Jul 6 - Jul 7
Friends Lake Inn
Exterior

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins
2.0 star property
Chestertown
9.2 out of 10, Wonderful, (148 reviews)
  • cleanliness
    Unwind just a minute from the sandy shores of Loon Lake, where a serene beach retreat awaits with beach toys, firepit, and hiking trails.
The price is ￥28,271
￥31,381 total
includes taxes & fees
Jun 29 - Jun 30
Pine Tree Motel & Cabins
Exterior

Luzerne Court Motel

Luzerne Court Motel
2.5 star property
Lake Luzerne
9.4 out of 10, Exceptional, (319 reviews)
The price is ￥16,668
￥18,500 total
includes taxes & fees
Jun 28 - Jun 29
Luzerne Court Motel
Private beach, sun loungers, kayaking, rowing

The Juliana Resort

The Juliana Resort
2.5 star property
Diamond Point
8.8 out of 10, Excellent, (186 reviews)
  • cleanliness
    Escape to a pristine private beach with loungers, where kayaking, fishing, and water adventures await on the waterfront.
The price is ￥27,302
￥30,305 total
includes taxes & fees
Jun 28 - Jun 29
The Juliana Resort
Room, 2 Queen Beds, Non Smoking | Desk, free WiFi, bed sheets

Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George
2.0 star property
Lake George
8.2 out of 10, Very Good, (1,000 reviews)
The price is ￥12,780
￥14,186 total
includes taxes & fees
Jun 29 - Jun 30
Howard Johnson by Wyndham Lake George
Suite, 1 King Bed, Non Smoking, Jetted Tub | Premium bedding, pillowtop beds, individually decorated

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Country Inn & Suites by Radisson, Lake George (Queensbury), NY
3.0 star property
Queensbury
9.0 out of 10, Wonderful, (1,447 reviews)
  • cleanliness
    Seaside splendor awaits just minutes from this Lake George retreat, where beach days blend with pool relaxation and outdoor adventures.
The price is ￥24,434
￥27,121 total
includes taxes & fees
Jun 28 - Jun 29
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Free daily continental breakfast

Best Western of Lake George

Best Western of Lake George
2.5 star property
Lake George
7.6 out of 10, Good, (1,001 reviews)
The price is ￥13,773
￥15,289 total
includes taxes & fees
Jul 1 - Jul 2
Best Western of Lake George
Standard Cabin | Free WiFi, bed sheets

Countryside Inn

Countryside Inn
2.5 star property
Lake George
6.8 out of 10, (215 reviews)
The price is ￥10,272
￥11,403 total
includes taxes & fees
Jun 28 - Jun 29
Countryside Inn
Deluxe Room, 2 Queen Beds, Refrigerator & Microwave | Laptop workspace, iron/ironing board, free WiFi, bed sheets

Motel 6 Lake George, NY – Adirondacks

Motel 6 Lake George, NY – Adirondacks
2.5 star property
Lake George
9.0 out of 10, Wonderful, (186 reviews)
  • cleanliness
    Soak up the sun just minutes from the beach, with poolside relaxation and adventure trails that make this motel a perfect family escape.
The price is ￥11,793
￥13,088 total
includes taxes & fees
Jun 30 - Jul 1
Motel 6 Lake George, NY – Adirondacks
Indoor pool

La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George
3.0 star property
Lake George
8.8 out of 10, Excellent, (1,684 reviews)
The price is ￥21,693
￥24,077 total
includes taxes & fees
Jun 29 - Jun 30
La Quinta Inn & Suites by Wyndham Lake George
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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Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included

Top Chestertown Hotel Reviews

The Georgian Lakeside Resort

The Georgian Lakeside Resort

10/10 Excellent
"Room was clean and staff was friendly "
Laura 1-night trip
Posted 13 hours ago
The Georgian Lakeside Resort

Frequently asked questions

What is Chestertown like for travelers who love the beach?
Known for its lakeside setting, Chestertown offers a lot for the traveler planning a getaway.
What's the best accommodation to stay near the beach in Chestertown?
The Fern Lodge is a top beach B&B with free breakfast and 8 hot tubs, and it's located close to Loon Lake Beach.
When's the best time for a beach vacation in Chestertown?
Plan your trip to the beach with a look at the seasons in Chestertown: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall.
What is there to see and do around Chestertown?
After arriving and checking into your hotel, you'll probably want to explore your surroundings. If you're eager to check out the beaches, head to Rogers Memorial Park Beach or Veterans Memorial Park Beach for some relaxation by the water. Discover the area's lakeside setting, and make time for local attractions like Loon Lake Beach and Friends Lake. Other things to see and do in the area are Hudson River and Loon Lake.
What's the best way to get to my beach hotel in Chestertown?
Here's some information to help you get to and around your beach accommodation in Chestertown more easily: Make your way to Chestertown with a flight to Glens Falls, NY (GFL-Floyd Bennett Memorial), the closest major airport which is located 23.6 mi (38 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.