Photo by Patricia Knorr

Search B&B in Chester

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare B&B in Chester with updated reviews, rates, and availability.

Porch
Hummingbird Inn
3.5 star property
10.0 out of 10, Exceptional, (63)
"Wonderful stay at this cozy B&B. Proprietors are kind and helpful, and make an amazing breakfast. Rooms are bright and spacious with all the necessary amenities. Looking forward to visiting again during summer months. "
The price is NT$10,081
per night
May 28 - May 29
Hummingbird Inn
Lake
Inn at Huntingfield Creek
3.5 star property
10.0 out of 10, Exceptional, (44)
"Lovely property with wonderful owners and staff, including three very welcoming dogs. We had a perfect weekend getaway."
The price is NT$7,395
per night
May 29 - May 30
Inn at Huntingfield Creek
Front of property
The Oaks Waterfront
4.0 star property
9.8 out of 10, Exceptional, (48)
"Beautiful facility and grounds and friendly staff."
The Oaks Waterfront
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Chesapeake Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar
Flag House Inn
3.5 star property
9.8 out of 10, Exceptional, (48)
"Very close to downtown!"
The price is NT$9,624
per night
May 28 - May 29
Flag House Inn
Beach nearby
Inn at Horn Point
3.0 star property
9.6 out of 10, Exceptional, (18)
"I booked the trip to celebrate an anniversary weekend away with my husband. The property came up through a Yelp review so I checked it out. I was impressed with the location, the detail to cleanliness, and the commitment to the environment. Once I booked the room, the innkeepers were very helpful in offering things to do and places to eat, as well as offering to help make our anniversary stay more memorable. Once we arrived, Cory took the time to greet us as we came in and share some of the...
The price is NT$11,330
per night
May 28 - May 29
Inn at Horn Point
Porch
Parsonage Inn
3.5 star property
9.2 out of 10, Wonderful, (119)
"The owners were great hosts"
The price is NT$7,408
per night
May 29 - May 30
Parsonage Inn
View from property
Laurel Grove Inn on the South
3.5 star property
9.0 out of 10, Wonderful, (505)
"It was a short stay. We are local and wanted a nice place to stay while we were having noisy plumbing repairs done at home. Tiffany, the inn keeper, Was very accommodating for my elderly wheelchair-bound mother. Views of the river were beautiful. I look forward to coming sometime when I can stay and perhaps kayak the river."
The price is NT$5,959
per night
Jun 16 - Jun 17
Laurel Grove Inn on the South
Outdoor pool
Black Walnut Point Inn
3.5 star property
9.0 out of 10, Wonderful, (53)
"Wife and I stayed 3 days for 41st anniversary. Bob and Tracy are wonderful hosts. "
The price is NT$5,741
per night
May 29 - May 30
Black Walnut Point Inn
Luxury Suite, Garden View (Rutland Suite) | Egyptian cotton sheets, premium bedding, pillowtop beds
The Annapolis Inn
4.0 star property
9.0 out of 10, Wonderful, (4)
"The Annapolis Inn exceed every expectation! The owners are absolutely fabulous. The property is gorgeous and exceptionally appointed. Alex is a gourmet chef who left us wanting more each breakfast. Joe is a tremendous story teller and you will want to sit for hours listening and conversing. Both are wonderful and kind humans who gave us their undivided attention and complete care. This was my first experience at a bed and breakfast and I am forever spoiled. You won’t find better accommodations...
The Annapolis Inn
Exterior
George Brooks House B&B
3.0 star property
8.6 out of 10, Excellent, (51)
"We loved that the historic house was built by the son of freedenslaved African Americans."
The price is NT$8,696
per night
May 28 - May 29
George Brooks House B&B
Boating
Robert Morris Inn
3.0 star property
8.4 out of 10, Very Good, (279)
"Beautiful resort, outdated but clean. We went on the weekend before ownership changed so the menu was limited and the breakfast was undercooked but the server was AWESOME! He remembered us and catered to us like we were the only customers."
Robert Morris Inn
Horseback riding
The Inn at Tacaro Estate
4.5 star property
8.0 out of 10, Very Good, (4)
"It was amazing. The place was nicely decorated. Food was great. Highly recommended."
The price is NT$13,845
per night
May 22 - May 23
The Inn at Tacaro Estate
Don't see what you're looking for?
See all available properties in Chester
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.

Other property types in Chester

Chester B&B information

Number of reviews
Accommodation
 B&B
Lowest Price
Highest Price

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: Parsonage Inn: 8 rooms. 13.3 mi (21.4 km) from the heart of Chester. Enjoy the free full breakfast and unique décor. George Brooks House B&B: 6 rooms. 12.7 mi (20.5 km) from the downtown core. Enjoy the library and fireplace in the lobby. 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. Hummingbird Inn: 6 rooms. Located 18.2 mi (29.2 km) from the core of Chester. Enjoy the free full breakfast and massage services.
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.
What is there to do in Chester?
Spend some time exploring Eastern Neck National Wildlife Refuge and Sandy Point Beach if you’re hoping to see some of the area’s natural features. You might put Queenstown Premium Outlets and Sandy Point State Park on your list if you want to see more of the area.
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.

Recent reviews of Chester hotels
Expedia verified reviews

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

5/5 Excellent
"All was good for our stay. There is a charge for parking which I did not see indicated on the website before booking. "
A verified traveler stayed at Hilton Garden Inn Annapolis
Posted 2 days ago
Hilton Garden Inn Annapolis