Best Bed and Breakfast Chestertown - £123 B&Bs in Chestertown

Q: What are the best B&Bs in Chestertown?

Here are some B&Bs in the area: Inn at Huntingfield Creek : 12 rooms. 11.3 mi (18.2 km) from the city centre. Enjoy the local cuisine breakfast and Jetted bath. Inn at Haven Harbour : 24 rooms. Located 11 mi (17.7 km) from the core of Chestertown. Enjoy the on-site dining and outdoor pool.

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Our top choices for Chestertown bed & breakfast

Vandiver Inn

Havre De Grace

Danielle

includes taxes & fees

25 Jun - 26 Jun

Flag House Inn

Historic District

Nathan

includes taxes & fees

21 Jun - 22 Jun

Inn at Huntingfield Creek

Rock Hall

Myrna

includes taxes & fees

16 Jul - 17 Jul

Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy

Smyrna

David W.

includes taxes & fees

30 Jun - 1 Jul

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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

10/10 Excellent

"We had an amazing stay at the Historic Inns of Annapolis and would absolutely stay here again. From the moment we arrived, the valet staff was incredible. Everyone was warm, welcoming, and genuinely helpful. One thing that really stood out was that they allowed us to keep our car with valet service until 2:00 p.m. on the day we checked out so we could spend a little more time exploring Annapolis before heading to the airport. That extra accommodation made a huge difference and was very much appreciated. The grounds and buildings are beautiful, and the historic charm throughout the property is amazing. Our room was comfortable, clean, and exactly what we hoped for in a historic inn. The only downside was the bathroom. The shower/tub area was very small. I'm not even 5 feet tall and barely 100 pounds, and it felt pretty cramped even for me. That said, it certainly wasn't enough to take away from an otherwise excellent stay. The bar was fantastic, and the bartender was awesome. I wish I could remember his name because he made the best chocolate martini I've ever had. While chatting with us, he even gave us a little tour of some of the downstairs historic lobby areas, which was such a nice touch and made us appreciate the property's history even more. Overall, everything was wonderful. Beautiful property, great staff, excellent service, and a perfect location. We'd absolutely stay here again and do it all over in a heartbeat."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"When we arrived people were still checking out because of the problem with the elevators. So we have to wait for the room to be cleaned. We booked a handicap room but was giving a standard room I called down to the desk and they did move us to a handicap room. The Restaurant was closed for remodeling. One of the two elevators was not working. The hallways were hot. The a/c was working in our room just fine. It could be a nice place to stay. The location is great for someone that wants to shop etc. I felt it was a little pricey."

Find out more about Chestertown

Chestertown B&B information

Number of reviews	713
Accommodation	6 B&B
Lowest Price	£123
Highest Price	£307

Frequently asked questions

Searching for B&Bs in Chestertown?

If you're interested in something a little more offbeat than the traditional hotel experience, a stay at a bed and breakfast could be a great option for your holiday. While you're enjoying your trip to Chestertown, Chestertown Dog Park and Urieville Park are perfect spots to get in some fresh air and greenery.

Why should you consider a B&B over a traditional hotel room?

Every B&B has a unique charm — whether it's a comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the tiny details are what make bed and breakfasts the perfect escape.

What are the best B&Bs in Chestertown?

Here are some B&Bs in the area: Inn at Huntingfield Creek: 12 rooms. 11.3 mi (18.2 km) from the city centre. Enjoy the local cuisine breakfast and Jetted bath. Inn at Haven Harbour: 24 rooms. Located 11 mi (17.7 km) from the core of Chestertown. Enjoy the on-site dining and outdoor pool.

When is the best time to book my B&B in Chestertown?

When you're planning your escape to Chestertown, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.

What is there to do in Chestertown?

When you want to explore some cultural attractions on your trip, Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater are worthy sites to visit. You should put Chestertown Historic District and Rolphs Wharf Marina on your list if you want to see more of the area.

How can I get to and around Chestertown?

You can plan your excursions in and around Chestertown ahead of time with these transportation options. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) away from the heart of the city. Otherwise, look for flights into Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, consider renting a car to explore more sights.

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