Book Chester Bed & Breakfast

Check prices for these dates

Next weekend
Apr 3 - Apr 5
In two weeks
Apr 10 - Apr 12
In one month
Apr 24 - Apr 26
In two months
May 22 - May 24

Our top choices for Chester bed & breakfast

Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (70 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
$153 nightly
The price is $168
Apr 1 - Apr 2
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, (62 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
$156 nightly
The price is $173
Mar 25 - Mar 26
Total with taxes and fees
Inn at Huntingfield Creek
Porch

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (131 reviews)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
$149 nightly
The price is $164
Mar 25 - Mar 26
Total with taxes and fees
Parsonage Inn
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (89 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
$174 nightly
The price is $199
Mar 25 - Mar 26
Total with taxes and fees
Flag House Inn
Front of property

Hummingbird Inn

Hummingbird Inn
3.5 star property
Easton
10.0 out of 10, Exceptional, (87 reviews)
"Our stay was excellent in every single way. "
United States
Darren
$301 nightly
The price is $331
Mar 25 - Mar 26
Total with taxes and fees
Hummingbird Inn
Seasonal outdoor pool, pool umbrellas, sun loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
$286 nightly
The price is $326
Mar 25 - Mar 26
Total with taxes and fees
The Inn at Tacaro Estate
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, (41 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
$489 nightly
The price is $538
Mar 25 - Mar 26
Total with taxes and fees
The Oaks Waterfront
Terrace/patio

Inn at Horn Point

Inn at Horn Point
3.0 star property
Eastport
9.6 out of 10, Exceptional, (21 reviews)
"Family owned with care and pride. Excellent food and recommendations for other restaurants and activities. "
United States
Andrew
$524 nightly
The price is $597
Apr 9 - Apr 10
Total with taxes and fees
Inn at Horn Point
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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Excellent hotel "
Samuel 4-night trip
Posted 2 hours ago
Sonesta ES Suites Annapolis

Find out more about Chester

Chester B&B information

Number of reviews
480
Accommodation
14 B&B
Lowest Price
$164
Highest Price
$597

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 $164 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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