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Find a Bed and Breakfast in Chestertown from CA $682

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Chestertown B&B

The Fern Lodge
Relax by the water's edge in this serene outdoor seating area, complete with a fire pit and comfortable seating.

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (47)
"We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer."
The price is CA $682
CA $758 total
includes taxes & fees
Sep 8 - Sep 9
The Fern Lodge
Rockwell Falls Inn and Wine Bar
Relax on the covered porch with wicker chairs and a glass table, surrounded by lush greenery and hanging flower baskets.

Rockwell Falls Inn and Wine Bar

3.5 star property
9.4 out of 10, Exceptional, (212)
"Beautiful room (Sunrise Suite), delicious breakfast, friendly staff, comfy porch for reading! Wish there could have been a few more choices for dinner food with our wine in the evening."
Rockwell Falls Inn and Wine Bar
4-bedroom bed & breakfast in distinct North Creek, with a rustic cozy cabin feel
Interior

4-bedroom bed & breakfast in distinct North Creek, with a rustic cozy cabin feel

4-bedroom bed & breakfast in distinct North Creek, with a rustic cozy cabin feel
The Loft at The Remington
Interior

The Loft at The Remington

3.5 star property
The Loft at The Remington
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

Surfside On The Lake

Surfside On The Lake

10/10 Excellent
"Beautiful view of the lake. Will definitely go back"
Tammy 2-night trip
Posted 22 hours ago
Surfside On The Lake