Bed and Breakfast in Chestertown, MD

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7 nights
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Chestertown, MD bed and breakfast
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Chestertown, MD Bed and breakfast: no available offers. Here are other great options for your stay!

Magnolia House Is For Sale! Historic Chestertown - Chestertown, MD
10 60 reviews

Magnolia House Is For Sale! Historic Chestertown

apartment, Chestertown
This charming 3-bedroom apartment is situated in the historic district of Chestertown, just a short walk from the bustling High Street and two blocks from the picturesque Chester River. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment offers ample space for families or groups of friends, with three bathrooms and a capacity of six guests. Enjoy modern amenities such as a fully equipped kitchen, a washer and dryer, a gas fireplace, and a private garden with a screened porch and a brick terrace, perfect for relaxing evenings.
Circa 1900 Home In The Heart Of Historic Downtown Chestertown - Chestertown, MD
10 89 reviews

Circa 1900 Home In The Heart Of Historic Downtown Chestertown

apartment, Chestertown
This family-friendly house is situated in the centre of Chestertown, just half a mile from Washington College and 4.6 miles from Rolphs Wharf Marina. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and convenient stay.
The property offers four bedrooms, accommodating up to six guests, making it ideal for families or groups of friends. Amenities include a fully equipped kitchen, a private garden, a terrace or balcony, a spa, and parking, ensuring a relaxing and enjoyable stay.
Cozy Carriage House - Chestertown, MD
9.7 194 reviews

Cozy Carriage House

house, Chestertown
This Chestertown carriage house, situated at the rear of a Victorian property, offers a peaceful retreat a short walk from the town centre.
The property comprises a fully equipped kitchen, modern bathroom, and private garden with covered parking including EV charging; sleeping two guests, it provides all linens and towels.
Pet-friendly Home On Chester River W/ Dock! - Chestertown, MD
9.4 25 reviews

Pet-friendly Home On Chester River W/ Dock!

apartment, Kingstown
This Chestertown holiday home, located less than 1.6km from Kings Town Park and under 3.2km from the Garfield Centre for the Arts and Wilmer Park, offers convenient access to Kingstown's cultural attractions.
The 300 square metre property boasts a spacious layout with four bedrooms, five bathrooms, and ample room for up to fourteen guests, featuring a private pool, fully equipped kitchen, and outdoor amenities including a terrace and garden.

Frequently asked questions about bed and breakfast in Chestertown, MD

  • What are the must-see sights for first-time visitors on a day trip to Chestertown, MD region?

    For a day trip, you'll want to check out the historic Chestertown waterfront. The charming shops and restaurants along High Street are a must, and you can't miss the beautiful colonial architecture of the Washington College campus. A short walk from the waterfront is the historic Wilmer Park, a lovely green space perfect for a picnic.
  • 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 weather can travelers expect when exploring nature in Chestertown, MD?

    Chestertown has four distinct seasons. Summers are warm and humid, with temperatures averaging around 25°C. Winters are mild, with average temperatures around 5°C, but it can get chilly with the wind. Spring and autumn are beautiful, with mild temperatures and stunning foliage.
  • 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 outdoor activities can visitors enjoy in and around Chestertown, MD?

    Chestertown is a great place for outdoor activities. You can enjoy hiking and biking on the Chester River Trail, kayaking or canoeing on the Chester River, or fishing from the banks of the river. There's also the beautiful Wilmer Park, perfect for a stroll or a picnic.
  • 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 famous cities can be easily accessed from Chestertown, MD?

    Chestertown is a great base for exploring the Eastern Shore of Maryland. Baltimore, with its vibrant Inner Harbor and historic Fells Point, is about a 90-minute drive. Washington D.C., with its world-class museums and monuments, is about a two-hour drive. And if you're looking for a beach getaway, Ocean City is about a two-hour drive.
  • 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 local breakfast specialties can you enjoy in Chestertown, MD region?

    Start your day with a classic Chesapeake Bay breakfast at one of Chestertown's local restaurants. Try a crab cake Benedict, a Chesapeake Bay crab omelet, or a breakfast sandwich with locally sourced ingredients. You'll find plenty of options for a delicious and hearty breakfast.
  • 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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