Find a Bed and Breakfast in Chester from CA $214

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Our top choices for Chester bed & breakfast

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (72 reviews)
"A beautiful renovated historical house with charm, clean rooms, decorative furnishings and a wonderful hot breakfast. What we enjoyed the most was the warm hospitality of Willard, Valerie, and the other staff. Very close to downtown St. Michael’s, but just far enough away to give a nice feel of natural serenity. Great for a quick getaway from the city. We will be back. "
United States
Charles
The price is CA $214
CA $235 total
includes taxes & fees
Apr 16 - Apr 17
George Brooks House B&B

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
The price is CA $193
CA $214 total
includes taxes & fees
Apr 20 - Apr 21
Inn at Huntingfield Creek

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (133 reviews)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is CA $220
CA $242 total
includes taxes & fees
Apr 19 - Apr 20
Parsonage Inn

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
"The B&B website and other on-line links claims "...excellent breakfast" and "the best breakfast in Annapolis". What was served were mini grocery store bought pastry, no fresh coffee, no juice, no plates, no one around. In addition, they state that for a large fee you can have valet parking on-site. There was no valet. I requested a refund for the valet parking and used that money to have a decent breakfast elsewhere. "
United States
Linda
The price is CA $250
CA $285 total
includes taxes & fees
Apr 20 - Apr 21
Flag House Inn

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
The price is CA $355
CA $404 total
includes taxes & fees
Apr 27 - Apr 28
The Inn at Tacaro Estate

Hummingbird Inn

Hummingbird Inn
3.5 star property
Easton
10.0 out of 10, Exceptional, (89 reviews)
" Staff is super friendly. The rooms were very clean and the breakfast was wonderful."
United States
Lewis
The price is CA $408
CA $448 total
includes taxes & fees
Apr 16 - Apr 17
Hummingbird Inn

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
The price is CA $606
CA $666 total
includes taxes & fees
Apr 16 - Apr 17
The Oaks Waterfront
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.
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Top Chester Hotel Reviews

Find out more about Chester

Chester B&B information

Number of reviews
504
Accommodation
13 B&B
Lowest Price
CA $214
Highest Price
CA $666

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: Flag House Inn: 5 rooms. 10.6 mi (17 km) from the heart of Chester. Enjoy the unique décor and fireplace in the lobby. George Brooks House B&B: 6 rooms. 12.7 mi (20.5 km) from the downtown core. Enjoy the library and fireplace in the lobby. Parsonage Inn: 8 rooms. Situated 13.4 mi (21.5 km) from the heart of Chester. Enjoy the free full breakfast and unique décor. The Oaks Waterfront: 15 rooms. 17 mi (27.4 km) from the heart of downtown. Enjoy the free cooked breakfast and rooftop terrace. Hummingbird Inn: 6 rooms. Located 18.2 mi (29.2 km) from the core of Chester. Enjoy the free full breakfast and massage services.
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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