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Book Bed and Breakfast in Chestertown

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Featured B&B in Chestertown

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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.

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.

Hotel Options in Chestertown

    Holiday Inn Express Hotel & Suites Chestertown, an IHG Hotel

    Holiday Inn Express Hotel & Suites Chestertown, an IHG Hotel

    150 Scheeler Road, Chestertown, MD
    The price is $85 per night from Apr 25 to Apr 26
    4.2/5Very Good! (24 reviews)
    Holiday Inn Express Hotel & Suites Chestertown, an IHG Hotel
    Great Oak Manor

    Great Oak Manor

    10568 Cliff Rd, Chestertown, MD
    The price is $159 per night from Apr 25 to Apr 26
    Great Oak Manor
    Red Roof Inn & Suites Chestertown

    Red Roof Inn & Suites Chestertown

    160 Scheeler Rd, Chestertown, MD
    The price is $85 per night from May 5 to May 6
    3.9/5Very Good! (12 reviews)
    Red Roof Inn & Suites Chestertown