Photo by Patricia Knorr

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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

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

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 768
AED 875 total
includes taxes & fees
4 Mar - 5 Mar
Flag House Inn
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (125)
"Great stay. We will be returning"
The price is AED 661
AED 727 total
includes taxes & fees
4 Mar - 5 Mar
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
4 Mar - 5 Mar
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 969
AED 1,105 total
includes taxes & fees
9 Mar - 10 Mar
The Inn at Tacaro Estate
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 1,050
AED 1,155 total
includes taxes & fees
4 Mar - 5 Mar
Hummingbird Inn
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"Beautiful resort, outdated but clean.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
The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (31)
" Beautiful property, wonderful staff, excellent food service."
The price is AED 1,418
AED 1,560 total
includes taxes & fees
17 Mar - 18 Mar
The Oaks Waterfront
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 448
AED 498 total
includes taxes & fees
7 Mar - 8 Mar
Inn at Huntingfield Creek
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 1,316
AED 1,500 total
includes taxes & fees
4 Mar - 5 Mar
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
The Annapolis 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
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
Cass-N-Reel Luxury Houseboat
Smart TV

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (21)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
Sweet Bamboo Beach Cottage
Fridge, microwave, oven, stovetop

Sweet Bamboo Beach Cottage

9.8 out of 10, Exceptional, (70)
"Couldn’t be happier with our stay. The house was exactly as pictured. Neighborhood was quiet with a small town feel. Most of the major appliances appeared relatively new, the beds were comfortable and the house was staffed with an abundance of linens and towels. Front and back yards are completely fenced in which is perfect for those with small dogs. North Beach is only a short drive from College Park, Baltimore and Annapolis. Check in was a breeze. Would definitely consider staying there...
Sweet Bamboo Beach Cottage
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 surrounding area: The Oaks Waterfront: 15 rooms. 17 mi (27.4 km) from the downtown core. Enjoy the free cooked breakfast and rooftop terrace. Flag House Inn: 5 rooms. Situated 10.6 mi (17 km) from the heart of Chester. Enjoy the local cuisine breakfast and unique décor. Parsonage Inn: 8 rooms. 13.3 mi (21.4 km) from the heart of downtown. Enjoy the free full breakfast and unique décor. George Brooks House B&B: 6 rooms. Located 12.7 mi (20.5 km) from the core of Chester. Enjoy the library and fireplace in the lobby.
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.