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
May 29 - May 31
In two weeks
Jun 5 - Jun 7
In one month
Jun 19 - Jun 21
In two months
Jul 17 - Jul 19

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, (63 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
$178 nightly
The price is $198
May 25 - May 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, (134 reviews)
"We really enjoyed our stay at The Parsonage. The property and room were kept well. The staff were sweet and attentive. Very good location as far as walking distance to shops, restaurants and the waterfront area. I would certainly return and certainly recommend to anyone visiting St. Michael’s. "
United States
Katie
$180 nightly
The price is $198
May 25 - May 26
Total with taxes and fees
Parsonage Inn
Front of property

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
$329 nightly
The price is $362
May 21 - May 22
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
9.6 out of 10, Exceptional, (15 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
$303 nightly
The price is $346
May 27 - May 28
Total with taxes and fees
The Inn at Tacaro Estate
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
"Great location. Beautiful room and exemplary service. "
United States
Nathan
$227 nightly
The price is $259
May 25 - May 26
Total with taxes and fees
Flag House Inn
Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (72 reviews)
"Mr Will very good Host and breakfast very delicious sure we will come back ❤️"
United States
MENBERE
$319 nightly
The price is $351
May 22 - May 23
Total with taxes and fees
George Brooks House B&B
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
May 26 - May 27
Total with taxes and fees
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"The front desk was super helpful & the beds were exceptionally comfortable."
Jenna 1-night trip
Posted 2 hours ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Chester

Chester B&B information

Number of reviews
374
Accommodation
14 B&B
Lowest Price
$198
Highest Price
$538

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 $198 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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