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    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 3 - Oct 5
In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23

B&B in Chester

Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
8.6 out of 10, Excellent, (4)
"Steps to the 3rd floor attic Low headroom every where 4' to 5' headroom in front of the toilet 8 yr old banged his head Everything was good except the very small room Don't rent this room unless you're 4' tall I'm surprised it passed inspection "
$206 nightly
The price is $229
Sep 29 - Sep 30
Total with taxes and fees
Inn at Haven Harbour
The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (38)
"Loved the Oaks! Fabulous accommodations and excellent staff"
$459 nightly
The price is $505
Sep 28 - Sep 29
Total with taxes and fees
The Oaks Waterfront
Hummingbird Inn
Porch

Hummingbird Inn

3.5 star property
10.0 out of 10, Exceptional, (80)
"The Hummingbird Inn is a Ritz Carlton (service wise) disguised as a BnB. It’s cute, has charm, but moreover, you immediately feel a sincere sense of welcome. And the breakfast is first rate. Well done Mary and Eric!"
$313 nightly
The price is $344
Sep 28 - Sep 29
Total with taxes and fees
Hummingbird Inn
Laurel Grove Inn on the South
Outdoor dining

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (527)
"Great location with fantastic views. Very friendly owner "
$200 nightly
The price is $228
Oct 6 - Oct 7
Total with taxes and fees
Laurel Grove Inn on the South
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.6 out of 10, Excellent, (64)
"Gorgeous quaint historic house. Friendly owner, close to town "
$207 nightly
The price is $228
Sep 29 - Sep 30
Total with taxes and fees
George Brooks House B&B
Flag House Inn
Front of property

Flag House Inn

3.5 star property
9.4 out of 10, Exceptional, (78)
"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!"
$165 nightly
The price is $188
Sep 28 - Sep 29
Total with taxes and fees
Flag House Inn
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (130)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
$229 nightly
The price is $252
Sep 28 - Sep 29
Total with taxes and fees
Parsonage Inn
The Inn at Tacaro Estate
Horseback riding

The Inn at Tacaro Estate

5.0 star property
9.2 out of 10, Wonderful, (9)
"It was perfect!! We had a great stay. Luca was so kind and attentive. The property is astonishing. Perfect weekend retreat! Thank you so much "
$365 nightly
The price is $417
Sep 29 - Sep 30
Total with taxes and fees
The Inn at Tacaro Estate
Inn at Horn Point
Beach nearby

Inn at Horn Point

3.0 star property
9.6 out of 10, Exceptional, (21)
"Family owned with care and pride. Excellent food and recommendations for other restaurants and activities. "
$344 nightly
The price is $392
Sep 29 - Sep 30
Total with taxes and fees
Inn at Horn Point
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
Robert Morris Inn
Pool

Robert Morris Inn

3.0 star property
8.4 out of 10, Very Good, (280)
"Lovely historic building with amazing food and fun old books and art. "
Robert Morris Inn
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (53)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
$178 nightly
The price is $198
Sep 29 - Sep 30
Total with taxes and fees
Inn at Huntingfield Creek
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

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

10/10 Excellent
"Very clean and updated. Wonderful staff too"
Walter 1-night trip
Posted 1 day ago
Candlewood Suites Annapolis by IHG

Find out more about Chester

Find out more about Chester

Chester B&B information

Number of reviews
1,067
Accommodation
12 B&B
Lowest Price
$188
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 $188 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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