Book Bed and Breakfast in Chestertown

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured B&B in Chestertown

Don't see what you're looking for?
See all available properties in Chestertown
View all properties
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.

Hotel Options in Chestertown

    The Fern Lodge

    The Fern Lodge

    46 Fiddlehead Bay Rd. Chestertown NY
    $587 nightly
    The price is $652 total per night from Mar 18 to Mar 19
    $652 total
    Mar 18 - Mar 19
    Total with taxes and fees
    10/10 Exceptional! (52 reviews)
    Eagles Nest at Loon Lake near Gore Mountain

    Eagles Nest at Loon Lake near Gore Mountain

    Chestertown NY
    $680 nightly
    The price is $755 total per night from Mar 8 to Mar 9
    $755 total
    Mar 8 - Mar 9
    Total with taxes and fees
    10/10 Exceptional! (115 reviews)
    The Queensbury Hotel

    The Queensbury Hotel

    88 Ridge St Glens Falls NY
    $104 nightly
    The price is $115 total per night from Feb 22 to Feb 23
    $115 total
    Feb 22 - Feb 23
    Total with taxes and fees
    9.4/10 Exceptional! (1,520 reviews)

Bed and Breakfast

Book a bed and breakfast in Chestertown
A romantic getaway awaits when you book a bed and breakfast in Chestertown. The beauty of renting a B&B is that each one is unique. A farm B&B is cozy and rustic, while a luxury B&B provides top-of-the-line luxuries, including in-room jet tubs and thousand thread-count sheets. And let’s not forget the most important part of its name…breakfast! Bed & breakfasts are famous for putting out a great spread each morning. Fill your plate with fluffy pancakes with maple syrup, hot eggs right from the pan, and a cup of hot coffee to help get you ready for the rest of your day.

All are welcome at Chestertown bed n breakfasts
Some cheap accommodations are designed to simply give travelers a roof overhead and a comfortable bed to sleep on between adventures or business meetings. This definitely isn’t the case with a bed and breakfast (also known as a breakfast inn). The right B&B doesn’t just host your vacation to Chestertown, it becomes part of it. In many cases, travelers get to know the manager of the B&B, as well as mingle with other guests. Many B&Bs also arrange activities for guests, such as hikes in the area, bird watching outings, or fun game nights. 

B&B hotels have a reputation as a romantic retreat for couples. However, B&Bs are actually for all sorts of travelers. Book one with a parent, child, or your favorite travel buddy. Want to take your fur child on your adventure to Chestertown? A quick search through Orbitz will bring up pet-friendly B&B options so your best friend can come along.

Chestertown B&B essential information

Accommodation
4 B&B
Lowest Price
$115
Highest Price
$755
Popular accommodation
The Fern Lodge, Rockwell Falls Inn and Wine Bar, 4-bedroom bed & breakfast in distinct North Creek, with a rustic cozy cabin feel, The Loft at The Remington

More to Explore