Book Bed & Breakfasts in Chestertown, USA

Find your next stay with 2,200,000+ Hotels, Homes, Apartments & Villas

magnifying-glass.svgclose.svg
January 2026
Jan 2026
MonTueWedThuFriSatSun
Feb 2026
MonTueWedThuFriSatSun

Thursday 01 January 2026 - Friday 02 January 2026 (1 night)

calender.png
01 Jan 2026
Thursday
calender.png
02 Jan 2026
Friday
people.png
2 Adults - 0 Child
1 room

Chestertown - 1 Bed & Breakfasts to Choose From

Find deals where other travellers are staying
See map view
best price
Best Price Guarantee

We guarantee we won't be beaten on price. If you find a cheaper hotel deal on another website after you book with us, we’ll refund the difference!

See the latest prices and deals by choosing your dates. Choose dates

The Fern Lodge

46 Fiddlehead Bay Rd., Chestertown, USA - See map
Free WiFiParking availableDining servicesAmenities

Exceptional

40 Guest reviews

9.8
Cleanliness9.8/10
Service9.8/10
Comfort9.8/10
Condition9.8/10
location9.2/10
Neighborhood9.6/10
Quality10/10
Value10/10
Amenities9.8/10
Check Availability
See all bed & breakfasts in Chestertown

Explore Chestertown

Discover new destinations in Chestertown and find your next stay!
Loading...

Search by Holiday Style

Discover your ideal stay: explore pet-friendly homes, eco retreats, luxury accommodations, and more
Loading...

FAQs About Bed & Breakfasts in Chestertown

What's the best place to stay in Chestertown, New York, USA?
plus-blue.svg
There are several great places to stay in Chestertown, New York, USA including The Fern Lodge and Friends Lake Inn.
What's the best place to stay on a budget in Chestertown, New York, USA?
plus-blue.svg
For budget-friendly options in Chestertown, consider The Alpine Lodge or The Sunset Mountain Lodge.
What are some family-friendly bed-breakfasts in Chestertown, New York, USA?
plus-blue.svg
Some family-friendly bed and breakfast options in Chestertown include The Loon Lake Lodge and The Carol Theatre.
What's the best accommodation for a romantic getaway to Chestertown, New York, USA?
plus-blue.svg
For a romantic getaway, consider staying at The Friends Lake Inn or The Copperfield Inn Resort.
What's the best accommodation for an all-inclusive stay in Chestertown, New York, USA?
plus-blue.svg
Unfortunately, there are no all-inclusive accommodations in Chestertown, but many places offer inclusive packages.
Where can I find pet-friendly bed-breakfasts in Chestertown, New York, USA?
plus-blue.svg
Some pet-friendly bed and breakfast options in Chestertown include The Black Mountain Lodge and The Bailey House.
What's the best boutique bed-breakfasts in Chestertown, New York, USA?
plus-blue.svg
The Adirondack House Bed & Breakfast and The Big Moose Inn are great boutique bed and breakfast options in Chestertown.
What's the best spa bed-breakfasts in Chestertown, New York, USA?
plus-blue.svg
For a spa bed and breakfast experience, you can consider The Lake Placid Lodge or The Mirror Lake Inn Resort and Spa.
What bed-breakfasts in Chestertown, New York, USA have nice views?
plus-blue.svg
The Lake George Boathouse Bed & Breakfast and The Hedges on Blue Mountain Lake offer stunning views in Chestertown.
Do bed-breakfasts in Chestertown, New York, USA offer airport transportation services?
plus-blue.svg
Most bed and breakfasts in Chestertown do not offer airport transportation services. It's recommended to arrange transportation in advance.
Destination

Discovering Chestertown's Coastal Charm and Urban Wonders

Discover what to do and what to see in Chestertown

Welcome to Chestertown, New York, USA! A hidden gem nestled in the heart of the Adirondack Mountains, this picturesque town is brimming with charm and natural beauty. With its tranquil lakes, towering peaks, and friendly atmosphere, Chestertown is the perfect destination for those seeking a peaceful retreat. One of the highlights of a visit to Chestertown is exploring its historic landmarks. Step back in time and wander through the quaint streets lined with beautiful Victorian homes. Marvel at the stunning architecture of the Chester Inn, a beloved local landmark. For nature enthusiasts, a trip to the nearby Pharaoh Lake Wilderness Area is a must. Here, you can hike through lush forests, fish in pristine lakes, and admire the breathtaking views of the surrounding mountains. When it comes to accommodations, look no further than the bed and breakfasts in Chestertown listed on Travala.com. These charming establishments offer a cozy and intimate stay, allowing you to truly experience the essence of this enchanting town. From rustic cabins nestled in the woods to elegant Victorian mansions, there is a bed and breakfast to suit every taste. Booking your stay is made easy with a variety of payment options. Whether you prefer to pay with your credit card, debit card, or even cryptocurrencies like Bitcoin, Travala.com has got you covered. Our secure payment gateway ensures hassle-free transactions, giving you peace of mind as you plan your trip to Chestertown. Escape the hustle and bustle of everyday life and immerse yourself in the beauty of Chestertown. Discover its charming landmarks, breathe in the fresh mountain air, and create memories that will last a lifetime. Book your bed and breakfast accommodation now on Travala.com and embark on a truly unforgettable journey to Chestertown, New York, USA.

Read more

Continue Your Adventure

  • All Cities in the USA
  • Explore More Hotels

Explore Our Travel Guides

  • Travel Planning
  • CRYPTO
  • Travel Destination
  • Accommodation Guides
  • Travel Trends
  • News

FAQs

      More Ways to Explore Chestertown, the USA

      See what else the USA has to offer
      Type of Accommodation in Chestertown, the USA
      Budget Options in Chestertown, the USA

      Customer Reviews
      What our customers say

      Crypto-friendly Bookings

      Your money’s good here.

      Loading...

      We pride ourselves on being the leading crypto-native travel platform. Pay for your travel anywhere in the world seamlessly using 100+ cryptocurrencies or traditional payments.