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Book Chester Bed & Breakfast

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Aug 15 - Aug 17
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Oct 3 - Oct 5

B&B in Chester

Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
10.0 out of 10, Exceptional, (1)
"We recently had the pleasure of staying at the Inn at Haven Harbour, specifically at their south location, and can't say enough good things about our experience! From the moment we arrived, we were captivated by the immaculate property and stunning surroundings. The views of the water were breathtaking, and having access to a private beach made our stay feel even more special. The amenities were top-notch, with a pool available for those who prefer a swim to the beach. The staff were incredibly...
$227 nightly
The price is $252
Aug 6 - Aug 7
Total includes taxes and fees
Inn at Haven Harbour
Laurel Grove Inn on the South
Outdoor dining

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (517)
"Beautiful property and lovely hosts."
$200 nightly
The price is $228
Aug 7 - Aug 8
Total includes taxes and fees
Laurel Grove Inn on the South
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.8 out of 10, Excellent, (61)
"Gorgeous quaint historic house. Friendly owner, close to town "
$243 nightly
The price is $267
Aug 6 - Aug 7
Total includes taxes and fees
George Brooks House B&B
The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (33)
"Loved the Oaks! Fabulous accommodations and excellent staff"
$459 nightly
The price is $505
Aug 6 - Aug 7
Total includes taxes and fees
The Oaks Waterfront
Flag House Inn
Front of property

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (73)
"Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!"
$140 nightly
The price is $159
Aug 6 - Aug 7
Total includes taxes and fees
Flag House Inn
The Inn at Tacaro Estate
Horseback riding

The Inn at Tacaro Estate

5.0 star property
9.2 out of 10, Wonderful, (9)
"1940’s estate is maintained to remind you of those times. There was a “Speak-EZ” in the basement they had open Friday and Saturday evenings. My room was spacious and included a balcony. Huge front lawn with a pool and a view to the Bay. "
$355 nightly
The price is $405
Aug 10 - Aug 11
Total includes taxes and fees
The Inn at Tacaro Estate
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (52)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
$189 nightly
The price is $210
Aug 6 - Aug 7
Total includes taxes and fees
Inn at Huntingfield Creek
Hummingbird Inn
Porch

Hummingbird Inn

3.5 star property
10.0 out of 10, Exceptional, (77)
"Hummingbird Inn is so gracious to all guests. I was there for a triathlon and Eric and Mary made sure I was taken care of to race! Love this Inn!"
$284 nightly
The price is $312
Aug 11 - Aug 12
Total includes taxes and fees
Hummingbird Inn
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (129)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
$229 nightly
The price is $252
Aug 6 - Aug 7
Total includes taxes and fees
Parsonage Inn
Inn at Horn Point
Beach nearby

Inn at Horn Point

3.0 star property
9.4 out of 10, Exceptional, (19)
"Family owned with care and pride. Excellent food and recommendations for other restaurants and activities. "
$344 nightly
The price is $392
Aug 6 - Aug 7
Total includes taxes and fees
Inn at Horn Point
Robert Morris Inn
Pool

Robert Morris Inn

3.0 star property
8.4 out of 10, Very Good, (279)
"Lovely historic building with amazing food and fun old books and art. "
Robert Morris Inn
Black Walnut Point Inn
Outdoor pool

Black Walnut Point Inn

3.5 star property
9.0 out of 10, Wonderful, (56)
"Wife and I stayed 3 days for 41st anniversary. Bob and Tracy are wonderful hosts. "
Black Walnut Point Inn
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Great visit "
Chris 6-night trip
Posted 21 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

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 $159 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.