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Check prices for these dates

Next weekend
12 Sep - 14 Sep
In two weeks
19 Sep - 21 Sep
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov

B&B in Chester

Our top choices for Chester bed & breakfast

Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
8.0 out of 10, Very Good, (3)
"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 "
The price is AED 641
AED 793 total
includes taxes & fees
15 Sep - 16 Sep
Inn at Haven Harbour
Flag House Inn
Front of property

Flag House Inn

3.5 star property
9.4 out of 10, Exceptional, (76)
"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!"
The price is AED 755
AED 861 total
includes taxes & fees
7 Sep - 8 Sep
Flag House Inn
Hummingbird Inn
Porch

Hummingbird Inn

3.5 star property
10.0 out of 10, Exceptional, (79)
"Hummingbird Inn is so gracious to all guests. I was there for a triathlon and Eric and Mary made sure I was taken care of to race! Love this Inn!"
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, (523)
"Great location with fantastic views. Very friendly owner "
The price is AED 661
AED 754 total
includes taxes & fees
5 Oct - 6 Oct
Laurel Grove Inn on the South
The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (38)
"The facility designed was out standing and the staff was very good. "
The price is AED 1,517
AED 1,669 total
includes taxes & fees
7 Sep - 8 Sep
The Oaks Waterfront
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!"
The price is AED 841
AED 925 total
includes taxes & fees
7 Sep - 8 Sep
Parsonage Inn
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.8 out of 10, Excellent, (63)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is AED 760
AED 836 total
includes taxes & fees
8 Sep - 9 Sep
George Brooks House B&B
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 "
The price is AED 1,058
AED 1,206 total
includes taxes & fees
15 Sep - 16 Sep
The Inn at Tacaro Estate
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. "
Inn at Huntingfield Creek
Inn at Horn Point
Beach nearby

Inn at Horn Point

3.0 star property
9.4 out of 10, Exceptional, (19)
"Family owned with care and pride. Excellent food and recommendations for other restaurants and activities. "
The price is AED 1,395
AED 1,590 total
includes taxes & fees
7 Sep - 8 Sep
Inn at Horn Point
Robert Morris Inn
Pool

Robert Morris Inn

3.0 star property
8.4 out of 10, Very Good, (279)
"Lovely historic building with amazing food and fun old books and art. "
Robert Morris Inn
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
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Great location - easy to walk to most anywhere. Parking a bit expensive but overall experience was great "
Jason 2-night trip
Posted 2 days ago
Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"There were two great guys at the bar; they were fun, friendly, and good company. The staff at the front desk was very knowledgeable and friendly."
Michele 3-night trip
Posted 5 days ago
Graduate by Hilton Annapolis

Frequently asked questions

Searching for B&Bs in Chester?
Whether you're on a romantic trip and want to stay somewhere quiet and intimate, or you're traveling solo and hoping to get some local recommendations, a B&B can be a good choice for many different types of travelers.
Are you thinking about a B&B instead of a traditional hotel?
With attentive service, an atmosphere suited to mingling with other guests, and of course a full breakfast to start the day, B&Bs all have a one-of-a-kind environment.
What are the top B&Bs in Chester?
Here are some B&Bs in the area: Inn at Haven Harbour: 24 rooms. 11.6 mi (18.7 km) from the heart of Chester. Enjoy the onsite dining and outdoor pool. Hummingbird Inn: 6 rooms. 18.2 mi (29.2 km) from the downtown core. Enjoy the free full breakfast and massage services. The Oaks Waterfront: 15 rooms. Situated 17 mi (27.4 km) from the heart of Chester. Enjoy the free cooked breakfast and rooftop terrace. Flag House Inn: 5 rooms. 10.6 mi (17 km) from the heart of downtown. Enjoy the local cuisine breakfast and unique décor. Laurel Grove Inn on the South: 5 rooms. Located 15.8 mi (25.4 km) from the core of Chester. Enjoy the deli and arcade game room.
What's the best time of year to book my B&B in Chester?
When you're planning your stay in Chester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chester is 56 inches.
How can I get to and around Chester?
You can map out your trip in and around Chester ahead of time with these transportation options. Fly into Easton, MD (ESN-Easton - Newnam), which is located 16.6 mi (26.7 km) from the city center. Otherwise, look for flights into Baltimore Washington Intl. Airport (BWI), which is 24.8 mi (39.9 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.