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

Book Chester Bed & Breakfast

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Jul 24 - Jul 26
In two weeks
Jul 31 - Aug 2
In one month
Aug 14 - Aug 16
In two months
Sep 11 - Sep 13

Our top choices for Chester bed & breakfast

Front of property

Hummingbird Inn

Hummingbird Inn
3.5 star property
Easton
10.0 out of 10, Exceptional, (92 reviews)
" Staff is super friendly. The rooms were very clean and the breakfast was wonderful."
United States
Lewis
$329 nightly
The price is $362
Jul 19 - Jul 20
Total with taxes and fees
Hummingbird Inn
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (42 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
$440 nightly
The price is $484
Jul 26 - Jul 27
Total with taxes and fees
The Oaks Waterfront
Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (75 reviews)
"Mr Will very good Host and breakfast very delicious sure we will come back ❤️"
United States
MENBERE
$235 nightly
The price is $259
Jul 20 - Jul 21
Total with taxes and fees
George Brooks House B&B
Lake

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (66 reviews)
"A beautiful place to spend a few days relaxing and enjoying nature. The owners are friendly, welcoming, and take excellent care of the property."
United States
Myrna
$200 nightly
The price is $223
Jul 19 - Jul 20
Total with taxes and fees
Inn at Huntingfield Creek
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
"Great spot with easy walking downtown or to the Academy. Very nice sitting rooms downstairs with fresh pastries for breakfast. "
United States
Tyler
$227 nightly
The price is $259
Jul 20 - Jul 21
Total with taxes and fees
Flag House Inn
Seasonal outdoor pool, pool umbrellas, sun loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (17 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
$378 nightly
The price is $431
Jul 19 - Jul 20
Total with taxes and fees
The Inn at Tacaro Estate
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

Historic Inns of Annapolis

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!"
Frederick 1-night trip
Posted 12 hours ago
Historic Inns of Annapolis

Find out more about Chester

Chester B&B information

Number of reviews
344
Accommodation
14 B&B
Lowest Price
$223
Highest Price
$484

Frequently asked questions

What is the nightly rate for a B&B in Chester?
Prices for B&Bs in Chester often vary, but you can find a great deal from $223 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
What is the difference between a Chester B&B and a hotel?
Every Chester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chester B&Bs.

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