Chester B&B: Find the Best Bed and Breakfast from CA $221

Q: What are the top B&Bs in Chester?

Here are some B&Bs in the area: Flag House Inn : 5 rooms. 10.6 mi (17 km) from the heart of Chester. Enjoy the unique décor and fireplace in the lobby. 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. Laurel Grove Inn on the South : 5 rooms. Situated 15.8 mi (25.4 km) from the heart of Chester. Enjoy the deli and arcade game room. The Oaks Waterfront : 15 rooms. 17 mi (27.4 km) from the heart of downtown. Enjoy the free cooked breakfast and rooftop terrace. Hummingbird Inn : 6 rooms. Located 18.2 mi (29.2 km) from the core of Chester. Enjoy the free full breakfast and massage services.

A coastal town with a marina, a bridge, and a highway.

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Our top choices for Chester bed & breakfast

A boat deck with a white bench and a view of a calm lake and distant trees.

1. Inn at Huntingfield Creek

Rock Hall

Christine

CA $221 total

includes taxes & fees

Nov 16 - Nov 17

A room with a dark blue wall, a fireplace with lit candles, a leather armchair, and a bookshelf with decorative items.

2. Flag House Inn

Historic District

Nathan

CA $352 total

includes taxes & fees

Oct 18 - Oct 19

3. Laurel Grove Inn on the South

Annapolis

Ruth

CA $291 total

includes taxes & fees

Nov 1 - Nov 2

A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

4. Parsonage Inn

Downtown St. Michaels

Paul

CA $390 total

includes taxes & fees

Nov 2 - Nov 3

A two-story house with a swimming pool, outdoor seating, and a covered patio area.

5. George Brooks House B&B

St. Michaels

Erin

CA $303 total

includes taxes & fees

Nov 2 - Nov 3

A residential street with parked cars, a sidewalk, and a tree.

6. Charming Living room in beautiful Annapolis with AC discount long stay

Historic District

CA $490 total

includes taxes & fees

Oct 27 - Oct 28

Two wooden chairs facing a calm body of water at sunset.

7. Inn at Horn Point

Eastport

JOHN

CA $728 total

includes taxes & fees

Oct 30 - Oct 31

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

8. The Oaks Waterfront

Easton

Jeffrey

CA $687 total

includes taxes & fees

Oct 19 - Oct 20

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Top Chester Hotel Reviews

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"The staff was awesome. Very professional and helpful. Our room was cleaned and well maintained. The food was great and the spa service was awesome as well."

Historic Inns of Annapolis

10/10 Excellent

"The convenience to downtown was the biggest plus for me. The Maryland Inn is on Main street so shopping and dining are an easy walk. I was in town for the Annapolis boat show so walking to and from the show was a fairly easy commute. The hotel was very clean, my room was well maintained each day. The only issue I had was the TV was not working but upon notification, it was fixed right away. Otherwise I'd say the only other thing that visitors will be surprised with is Check in is located at another hotel (all tied to same company), so there is a short walk to this property if you are getting dropped off. Overall impression - This is an OLD historic building and hotel - actually a meeting spot for the Annapolis Ghost Tours :-). So set your expectations for that, it is not an upscale, modern resort hotel experience. For me, it was perfect, and much better than some of the rental houses I've stayed in over the years. If you're excited about historic places and buildings, this will be a great experience for you."

St Michaels Inn

10/10 Excellent

"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."

Find out more about Chester

Chester B&B information

Number of reviews	935
Accommodation	15 B&B
Lowest Price	CA $221
Highest Price	CA $728

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: Flag House Inn: 5 rooms. 10.6 mi (17 km) from the heart of Chester. Enjoy the unique décor and fireplace in the lobby. 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. Laurel Grove Inn on the South: 5 rooms. Situated 15.8 mi (25.4 km) from the heart of Chester. Enjoy the deli and arcade game room. The Oaks Waterfront: 15 rooms. 17 mi (27.4 km) from the heart of downtown. Enjoy the free cooked breakfast and rooftop terrace. 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.

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.

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