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
Feb 13 - Feb 15
In two weeks
Feb 20 - Feb 22
In one month
Mar 6 - Mar 8
In two months
Apr 3 - Apr 5

Our top choices for Chester bed & breakfast

Lake

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (59 reviews)
"Quiet. Friendly staff. Beautiful grounds. Very clean."
United States
Brian
$156 nightly
The price is $173
Feb 8 - Feb 9
Total with taxes and fees
Inn at Huntingfield Creek
Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (67 reviews)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
$170 nightly
The price is $187
Feb 9 - Feb 10
Total with taxes and fees
George Brooks House B&B
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
Feb 9 - Feb 10
Total with taxes and fees
Parsonage 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, (41 reviews)
" Beautiful property, wonderful staff, excellent food service."
United States
Seth
$459 nightly
The price is $505
Feb 13 - Feb 14
Total with taxes and fees
The Oaks Waterfront
Front of property

Hummingbird Inn

Hummingbird Inn
3.5 star property
Easton
10.0 out of 10, Exceptional, (87 reviews)
"This place is the cutest and they are the nicest people! The breakfast is delicious!!"
Canada
Chrystine
$301 nightly
The price is $331
Feb 8 - Feb 9
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
$322 nightly
The price is $367
Feb 22 - Feb 23
Total with taxes and fees
The Inn at Tacaro Estate
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.4 out of 10, Exceptional, (86 reviews)
"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "
United States
Elizabeth
$174 nightly
The price is $199
Feb 9 - Feb 10
Total with taxes and fees
Flag House 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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Room was spotless. Staff was very courteous. Would highly recommended."
Jose 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Chester

Chester B&B information

Number of reviews
482
Accommodation
14 B&B
Lowest Price
$164
Highest Price
$505

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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