A waterfront town with a pier, dock, and several buildings.

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Check availability on Chestertown Pet-friendly Hotels

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

Our top choices for Chestertown pet-friendly hotels

Room

1. Friends Lake Inn

Friends Lake Inn
4.0 star property
Chestertown
8.6 out of 10, Excellent, (137 reviews)
"Great breakfast, very friendly staff and beautiful place"
United States
Pierre
The price is AED 426
AED 473 total
includes taxes & fees
8 Nov - 9 Nov
Friends Lake Inn
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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Top Chestertown Hotel Reviews

Frequently asked questions

What's the best pet-friendly hotel in Chestertown?
Pine Tree Motel & Cabins is a top pet-friendly option for your stay. Other good choices to stay with your pet include Waterfront 1860s Farmhouse, Private Hot Tub, Fire Pit, Pond, Canoe, Walk to Town and Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing.
What's the best time of year to travel to Chestertown with my pet?
When you're traveling with pets, keeping track of the weather can help you make the trip more safe and fun for everyone. 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 with your pet in Chestertown?
Known for its waterfront, Chestertown has lots to offer visitors. See the local sights and visit Loon Lake Beach and Friends Lake. While you're there, make sure you don't miss Loon Lake and Hudson River.