Compare bed and breakfast in Chestertown, MD from 100+ providers!

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Chestertown, MD B&B
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Chestertown, MD B&B: no available offers. Here are other great options for your stay!

Loft At Fountain Park - Prime Downtown Location - Chestertown, MD
9.9 86 reviews

Loft At Fountain Park - Prime Downtown Location

apartment, Chestertown
This Chestertown apartment is located in the heart of downtown, just steps from High Street's shops and restaurants, and within walking distance of Washington College and the Chester River. It has received excellent ratings for location, cleanliness, and overall experience.
The apartment is a spacious two-level home that can comfortably accommodate up to eight guests. It offers modern amenities like a fully equipped kitchen, air conditioning, and a private garden, perfect for enjoying a relaxing stay in Chestertown.
Lovely Home In Chestertown With Free Ev Charging - Chestertown, MD
10 95 reviews

Lovely Home In Chestertown With Free Ev Charging

apartment, Kingstown
This Kingstown apartment is located in a quiet section of Chestertown, just a block from the waterfront and within walking distance of shops, galleries, and restaurants. It has earned excellent ratings for user experience, location, and cleanliness.
This two-story rental offers ample space for up to seven guests and features a fully equipped kitchen, comfortable bedrooms, air conditioning, a garden, and parking. Guests can enjoy easy access to the waterfront, explore local attractions using the provided guidebook, and prepare meals in the modern kitchen.
Classic Victorian In Chestertown - Chestertown, MD
9.9 163 reviews

Classic Victorian In Chestertown

apartment, Chestertown
This Victorian row house is located in a quiet neighborhood in Chestertown, just a short walk from the historic district and the Chester River waterfront. The apartment consistently receives excellent ratings for its location, cleanliness, and overall guest experience.
The home offers four bedrooms, two and a half bathrooms, and a gourmet kitchen, perfect for families or groups. Enjoy the private garden, pond, and two porches, along with amenities like high-speed internet, EV charging, and on-street parking.
Great Oak Guest House Best- Gated Property - Chestertown, MD
9.8 8 reviews

Great Oak Guest House Best- Gated Property

apartment, Fairlee
This Fairlee apartment is conveniently located in Chestertown, Maryland, just a short distance from popular attractions like Great Oak Manor, Great Oak Landing Marina, and Jellyfish Joel's Beach Bar. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience.
The spacious home features three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Enjoy access to a fully equipped kitchen, a relaxing front porch, and a private garden, as well as amenities like air conditioning, parking, and internet.

Frequently Asked Questions about bed and breakfast in Chestertown, MD

  • What weather can travelers expect when exploring nature in Chestertown, MD?

    Chestertown has four distinct seasons. Summers are hot and humid, with temperatures often reaching the 80s. Winters are mild, with temperatures typically in the 40s. Spring and fall are beautiful times to visit, with mild temperatures and stunning foliage.
  • What are the best bed and breakfasts in Chestertown, MD?

    Among the B&Bs in Chestertown, MD, Piney Grove Farm, Private Room W/bath: Walk To Washington College and Brampton 1860 are the most popular ones.

  • What outdoor activities can visitors enjoy in and around Chestertown, MD?

    Chestertown is a great place for outdoor enthusiasts. You can go kayaking or canoeing on the Chester River, hiking or biking on the Chestertown Greenway, or fishing at one of the many piers along the waterfront.
  • What are the best bed and breakfasts with a pool in Chestertown, MD?

    The best B&B with a pool in Chestertown, MD is Piney Grove Farm.

  • What famous cities can be easily accessed from Chestertown, MD?

    Chestertown is located about an hour and a half drive from Baltimore and Washington, D.C., so you can easily visit these cities on a day trip. It's also about a three-hour drive from Philadelphia.
  • What are the best bed and breakfasts for families and kids in Chestertown, MD?

    The best B&B for families and kids in Chestertown, MD is Private Room W/bath: Walk To Washington College.

  • What local breakfast specialties can you enjoy in Chestertown, MD region?

    You can't beat a breakfast sandwich from The Coffee House on High Street. They're known for their fresh ingredients and delicious coffee. If you're looking for something a little more upscale, try the breakfast at The Inn at Perry Cabin. Their omelets are legendary.
  • What are the best pet friendly bed and breakfasts in Chestertown, MD?

    The best pet friendly B&B in Chestertown, MD is Piney Grove Farm.

  • What are the best bed and breakfasts with parking in Chestertown, MD?

    Piney Grove Farm, Private Room W/bath: Walk To Washington College and Brampton 1860 are the best B&Bs with parking in Chestertown, MD.

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