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

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Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

Our top choices for Chestertown bed & breakfast

A lakeside setting with a boat docked near the shore, surrounded by trees and a fire pit area with seating.

1. The Fern Lodge

The Fern Lodge
3.5 star property
Chestertown
9.8 out of 10, Exceptional, (59 reviews)
"Staff is great,friendly and helpful Loved our stay. Place is beautiful"
United States
robert
$426 nightly
The price is $473
Nov 2 - Nov 3
Total with taxes and fees
The Fern Lodge
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

Nordick's Inn

Nordick's Inn

8/10 Good
"Parking facile, gens très gentil, près du lac, très belle ville pour des vacances d’été, plusieurs restaurants à proximité"
Megan 1-night trip
Posted 3 hours ago
Nordick's Inn

Find out more about Chestertown

Chestertown B&B information

Number of reviews
59
Accommodation
3 B&B
Lowest Price
$473
Highest Price
$473

Frequently asked questions

What are the most popular Chestertown Bed & Breakfasts?
The Fern Lodge is an exceptional choice for travelers seeking a luxurious escape in Chestertown, boasting an impressive 10.0 rating. Nestled in a stunning mountain setting, it offers a breathtaking view that invites guests to immerse themselves in nature. The Lodge features onsite mountain biking and hiking, providing the great adventure for outdoor enthusiasts. Guests rave about the delightful breakfast options and the inviting lobby, creating a cozy atmosphere to unwind after a day of exploration.
What is the nightly rate for a Bed & Breakfast in Chestertown?
Prices for B&Bs in Chestertown often vary, but you can find a great deal from $473 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chestertown B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Chestertown?
The best time to book a B&B in Chestertown is during the late spring to early summer months, particularly from May to June. This period is characterized by pleasant temperatures, ideal for outdoor activities and exploring the charming town. With temperatures ranging from the mid-50s to the low 80s Fahrenheit, visitors can comfortably enjoy Chestertown's beautiful waterfront and historic architecture.

As the weather warms up, Chestertown comes alive with various festivals and events that celebrate local arts and culture. This is an excellent time for travelers who appreciate a vibrant community atmosphere and wish to experience the best of what the town has to offer, including farmers' markets and outdoor dining options.

For those looking for a more budget-friendly experience, November presents a wonderful opportunity to enjoy Chestertown in a quieter setting. During this month, you can witness the enchanting early signs of winter while taking leisurely strolls along the waterfront and enjoying the peaceful ambiance. The town's cozy charm shines through, making it a delightful choice for a relaxing getaway.
What is the difference between a Chestertown Bed and Breakfast and a hotel?
Every Chestertown B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chestertown B&Bs.

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