Chester B&B: Find the Best Bed and Breakfast from CA $278

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. Inn at Huntingfield Creek : 12 rooms. 10.1 mi (16.2 km) from the downtown core. Enjoy the local cuisine breakfast and jetted tubs. The Oaks Waterfront : 15 rooms. Situated 17 mi (27.4 km) from the heart of Chester. Enjoy the free cooked breakfast and rooftop terrace. 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.

A boat docked at a pier during twilight with a city skyline in the background.

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Our top choices for Chester bed & breakfast

1. Inn at Huntingfield Creek

Rock Hall

Christine

CA $278 total

includes taxes & fees

Sep 7 - Sep 8

2. George Brooks House B&B

St. Michaels

Erin

CA $324 total

includes taxes & fees

Sep 1 - Sep 2

3. Laurel Grove Inn on the South

Annapolis

Ruth

CA $285 total

includes taxes & fees

Sep 7 - Sep 8

4. Flag House Inn

Historic District

Tyler

CA $345 total

includes taxes & fees

Sep 1 - Sep 2

Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

5. The Oaks Waterfront

Easton

Jeffrey

CA $673 total

includes taxes & fees

Sep 1 - Sep 2

6. Hummingbird Inn

Easton

Lewis

CA $469 total

includes taxes & fees

Sep 1 - Sep 2

Seasonal outdoor pool, pool umbrellas, sun loungers

7. The Inn at Tacaro Estate

Tracys Landing

James

CA $629 total

includes taxes & fees

Sep 1 - Sep 2

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Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Clean room ,nice helpful staff and the shuttle service was 👍 great"

The Wildset

10/10 Excellent

"We very much enjoyed our stay! Staff is very friendly and helpful. The inn is run very professionally and it is very well maintained. The breakfast looked nice but I am gluten free so there were very limited items that were GF. One suggestion would be some sort of magnifying mirror in bathrooms for those who don’t see well. We will stay again when in the area!"

St Michaels Inn

8/10 Good

"The rooms, though dated, are clean. I did bring to the attention of the manager that the towel bar in my bathroom was coming off. The handrail to walk down the steps into the pool was also loose, which I think is a safety hazard. The manager acknowledged he knew about it, but despite tons of cosmetic work being done outside, which was a bit inconvenient, the hand rail was not tightened Staff was nice, especially Tamia at the front desk and Helena in the breakfast room. The rooms are spacious and the A/C works fine!"

The Tidewater Inn

10/10 Excellent

"We had a lovely stay at Tidewater Inn centrally located in downtown Easton within walking distance of charming shops and delicious restaurants. Our room was spacious and light filled. The bathroom was small but adequate. We ate at the restaurant in the hotel (Hunters Tavern) and had a fabulous meal. Will definitely be back."

Find out more about Chester

Chester B&B information

Number of reviews	820
Accommodation	14 B&B
Lowest Price	CA $278
Highest Price	CA $673

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. Inn at Huntingfield Creek: 12 rooms. 10.1 mi (16.2 km) from the downtown core. Enjoy the local cuisine breakfast and jetted tubs. The Oaks Waterfront: 15 rooms. Situated 17 mi (27.4 km) from the heart of Chester. Enjoy the free cooked breakfast and rooftop terrace. 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.

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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