Chester B&B: Find the Best Bed and Breakfast from CA $281

Q: What are the top B&Bs in Chester?

Here are some B&Bs in the area: Inn at Huntingfield Creek : 12 rooms. 10.1 mi (16.2 km) from the heart of Chester. Enjoy the local cuisine breakfast and jetted tubs. The Oaks Waterfront : 15 rooms. 17 mi (27.4 km) from the downtown core. Enjoy the free cooked breakfast and rooftop terrace. George Brooks House B&B : 6 rooms. Situated 12.7 mi (20.5 km) from the heart of Chester. Enjoy the library and fireplace in the lobby. Flag House Inn : 5 rooms. 10.6 mi (17 km) from the heart of downtown. Enjoy the unique décor and fireplace in the lobby.

A boat docked at a pier during twilight with a city skyline in the background.

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Our top choices for Chester bed & breakfast

Hummingbird Inn

Easton

Lewis

CA $457 total

includes taxes & fees

Jul 22 - Jul 23

Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

The Oaks Waterfront

Easton

Jeffrey

CA $680 total

includes taxes & fees

Jul 26 - Jul 27

George Brooks House B&B

St. Michaels

MENBERE

CA $327 total

includes taxes & fees

Jul 20 - Jul 21

Inn at Huntingfield Creek

Rock Hall

Myrna

CA $281 total

includes taxes & fees

Jul 19 - Jul 20

Flag House Inn

Historic District

Tyler

CA $364 total

includes taxes & fees

Jul 20 - Jul 21

Seasonal outdoor pool, pool umbrellas, sun loungers

The Inn at Tacaro Estate

Tracys Landing

James

CA $545 total

includes taxes & fees

Jul 28 - Jul 29

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Top Chester Hotel Reviews

Historic Inns of Annapolis

10/10 Excellent

"I loved the historic building- upgraded with 21stC amenities of course- like electricity and an elevator. Bed was very cozy. Bathroom window faced St. Mary's church and bedroom faced Capitol bldg. A short 2 block walk to a city owned parking garage, $24 for 24 hours. Not bad. And the restaurants all close by. I've been to Annapolis many times, but never overnight, so this was a great spot that my Lady absolutely adored!"

Courtyard by Marriott Annapolis

8/10 Good

"Overall, my stay at the Courtyard by Marriott in Annapolis had several strong positives, but also a few maintenance and safety concerns that should be addressed. The room was very clean, and the bed was extremely comfortable — both the mattress and pillows made for a great night’s sleep. Breakfast at the Bistro was delicious, and the staff throughout the hotel were friendly and welcoming. I also enjoyed the pool area, which was clean and pleasant. That said, there were some issues that took away from the experience. I cut my finger on a broken elevator button, which definitely needs repair. The whirlpool jets were not working, so it functioned more like a hot tub than an actual whirlpool. More concerning, several of the side exit doors appeared to be broken: guests could enter from the outside, but could not exit from the inside. This was inconvenient, but more importantly, it seems like a potential fire code and safety issue. With some attention to maintenance and safety, this could be a much better stay. The staff, cleanliness, comfortable room, breakfast, and pool area were all highlights, but the hotel should prioritize fixing the broken doors, elevator button, and whirlpool jets."

Find out more about Chester

Chester B&B information

Number of reviews	344
Accommodation	14 B&B
Lowest Price	CA $281
Highest Price	CA $680

Frequently asked questions

Searching for B&Bs in Chester?

Whether you're on a romantic trip and want to stay somewhere quiet and intimate, or you're traveling solo and hoping to get some local recommendations, a B&B can be a good choice for many different types of travelers.

Are you thinking about a B&B instead of a traditional hotel?

With attentive service, an atmosphere suited to mingling with other guests, and of course a full breakfast to start the day, B&Bs all have a one-of-a-kind environment.

What are the top B&Bs in Chester?

Here are some B&Bs in the area: Inn at Huntingfield Creek: 12 rooms. 10.1 mi (16.2 km) from the heart of Chester. Enjoy the local cuisine breakfast and jetted tubs. The Oaks Waterfront: 15 rooms. 17 mi (27.4 km) from the downtown core. Enjoy the free cooked breakfast and rooftop terrace. George Brooks House B&B: 6 rooms. Situated 12.7 mi (20.5 km) from the heart of Chester. Enjoy the library and fireplace in the lobby. Flag House Inn: 5 rooms. 10.6 mi (17 km) from the heart of downtown. Enjoy the unique décor and fireplace in the lobby.

What's the best time of year to book my B&B in Chester?

When you're planning your stay in Chester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chester is 56 inches.

How can I get to and around Chester?

You can map out your trip in and around Chester ahead of time with these transportation options. Fly into Easton, MD (ESN-Easton - Newnam), which is located 16.6 mi (26.7 km) from the city center. Otherwise, look for flights into Baltimore Washington Intl. Airport (BWI), which is 24.8 mi (39.9 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

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