Photo by Patricia Knorr

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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 12 B&B in Chester with updated reviews, rates, and availability.

The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (30)
"Beautiful decor, exceptional staff, food was delicious. Serene surroundings. Excellent stay!"
The price is AED 1,418
AED 1,560 total
includes taxes & fees
17 Apr - 18 Apr
The Oaks Waterfront
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (127)
"exceptional hosts: above and beyond for service, suggestions, accommodation, effort to assist . impressive found by accident, would reccommend and visit AGAIN"
The price is AED 643
AED 707 total
includes taxes & fees
6 Apr - 7 Apr
Parsonage Inn
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.6 out of 10, Excellent, (57)
"Very nice property, cozy and clean rooms, excellent service."
The price is AED 588
AED 646 total
includes taxes & fees
7 Apr - 8 Apr
George Brooks House B&B
The Inn at Tacaro Estate
Horseback riding

The Inn at Tacaro Estate

5.0 star property
8.8 out of 10, Excellent, (6)
"Amazing hospitality "
The price is AED 937
AED 1,068 total
includes taxes & fees
6 Apr - 7 Apr
The Inn at Tacaro Estate
Flag House Inn
Chesapeake Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (68)
"Comfortable stay, high quality amazing service. Within walking distance to everything "
The price is AED 1,025
AED 1,168 total
includes taxes & fees
6 Apr - 7 Apr
Flag House Inn
Hummingbird Inn
Porch

Hummingbird Inn

3.5 star property
10.0 out of 10, Exceptional, (74)
"The owner and staff are exceedingly gracious, we felt quite welcome. Our room is warmly decorated and comfortable from the bed to the linens to the rain shower and tiled bath. We want to come back next year for New Year’s Eve. The other guests mirror the owner and staff in that they are very friendly. Thank you Eric and Mary!!! Sincerely, James & Chrisy "
The price is AED 1,150
AED 1,265 total
includes taxes & fees
6 Apr - 7 Apr
Hummingbird Inn
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (49)
"We had a great stay at this nice inn. It is exactly what we are looking for: a quiet place on the eastern shore surrounded by nature. The cottage (one of seven) is spacious and well appointed. The bed is very comfortable. The tranquility of sitting on the back porch looking at the golden sunset beyond the vast field and tree line!! We took many walks across the 70 plus acre property to the shore and just absorbed the peace and sound of the wind blowing over the water. It’s amazing. The living...
The price is AED 613
AED 680 total
includes taxes & fees
6 Apr - 7 Apr
Inn at Huntingfield Creek
Robert Morris Inn
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
Inn at Horn Point
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 AED 1,116
AED 1,272 total
includes taxes & fees
13 Apr - 14 Apr
Inn at Horn Point
Black Walnut Point Inn
Outdoor pool

Black Walnut Point Inn

3.5 star property
9.0 out of 10, Wonderful, (55)
"Unique property in beautiful setting. Home made breakfast. Quiet and peaceful. Lives the cats that live here too."
Black Walnut Point Inn
Laurel Grove Inn on the South
View from property

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (513)
"Now I understand why the great ratings! What a wonderful place to stay. Beautiful views, comfortable with all the conveniences of home. Great hosts who go above and beyond to ensure your stay is fabulous. We will definitely return!"
Laurel Grove Inn on the South
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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Other property types in Chester

Waterfront Sunset Bayview: sleeps 6
Beach

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (12)
"Great house, great owner, family had a blast! Thank you!"
Waterfront Sunset Bayview: sleeps 6
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (210)
"We loved our visit to Annapolis, and our stay at 10 Randall was all that we’d imagined it would be.We wish the weather has been a tad warmer, but I don’t think John could have fixed that .We highly recommend this charming home."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (180)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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.

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: The Oaks Waterfront: 15 rooms. 17 mi (27.4 km) from the heart of Chester. Enjoy the free cooked breakfast and rooftop terrace. Parsonage Inn: 8 rooms. 13.3 mi (21.4 km) from the downtown core. Enjoy the free full breakfast and unique décor. George Brooks House B&B: 6 rooms. 12.7 mi (20.5 km) from the heart of downtown. Enjoy the library and fireplace in the lobby. Inn at Huntingfield Creek: 12 rooms. Located 10.1 mi (16.2 km) from the core of Chester. Enjoy the jetted tubs and spa.
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.