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

Book Chester Bed & Breakfast

Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

Our top choices for Chester bed & breakfast

Lake

1. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (73 reviews)
"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"
United States
Christine
$200 nightly
The price is $223
Sep 7 - Sep 8
Total with taxes and fees
Inn at Huntingfield Creek
Exterior

2. George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (77 reviews)
"This weekend was an anniversary gift for my daughter and her husband. They had a wonderful time and were highly complimentary of the accommodations, the delicious breakfast and the location."
United States
Erin
$212 nightly
The price is $233
Sep 10 - Sep 11
Total with taxes and fees
George Brooks House B&B
Land view from property

3. Laurel Grove Inn on the South

Laurel Grove Inn on the South
3.5 star property
Annapolis
9.2 out of 10, Wonderful, (530 reviews)
"Beautiful property and lovely hosts."
United States
Ruth
$180 nightly
The price is $205
Oct 1 - Oct 2
Total with taxes and fees
Laurel Grove Inn on the South
Lobby lounge

4. Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (97 reviews)
"Great spot with easy walking downtown or to the Academy. Very nice sitting rooms downstairs with fresh pastries for breakfast. "
United States
Tyler
$218 nightly
The price is $248
Sep 1 - Sep 2
Total with taxes and fees
Flag House Inn
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

5. The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (44 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
$440 nightly
The price is $484
Sep 13 - Sep 14
Total with taxes and fees
The Oaks Waterfront
Front of property

6. Hummingbird Inn

Hummingbird Inn
3.5 star property
Easton
10.0 out of 10, Exceptional, (96 reviews)
" Staff is super friendly. The rooms were very clean and the breakfast was wonderful."
United States
Lewis
$341 nightly
The price is $375
Sep 1 - Sep 2
Total with taxes and fees
Hummingbird Inn
Pool

7. The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (18 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
$441 nightly
The price is $502
Sep 1 - Sep 2
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Clean room ,nice helpful staff and the shuttle service was 👍 great"
mona 1-night trip
Posted 6 hours ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Chester

Chester B&B information

Number of reviews
820
Accommodation
15 B&B
Lowest Price
$205
Highest Price
$502

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 $205 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.

Explore a world of travel with Expedia