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Check prices for these dates

Next weekend
6 Mar - 8 Mar
In two weeks
13 Mar - 15 Mar
In one month
27 Mar - 29 Mar
In two months
24 Apr - 26 Apr

Our top choices for Chester bed & breakfast

Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (67 reviews)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is SAR 634
SAR 697 total
includes taxes & fees
2 Mar - 3 Mar
George Brooks House B&B
Lake

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (61 reviews)
"Quiet. Friendly staff. Beautiful grounds. Very clean."
United States
Brian
Inn at Huntingfield Creek
Porch

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (131 reviews)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is SAR 559
SAR 615 total
includes taxes & fees
2 Mar - 3 Mar
Parsonage Inn
Front of property

Hummingbird Inn

Hummingbird Inn
3.5 star property
Easton
10.0 out of 10, Exceptional, (87 reviews)
"This place is the cutest and they are the nicest people! The breakfast is delicious!!"
Canada
Chrystine
Hummingbird Inn
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.4 out of 10, Exceptional, (87 reviews)
"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "
United States
Elizabeth
The price is SAR 681
SAR 777 total
includes taxes & fees
1 Mar - 2 Mar
Flag House Inn
Seasonal outdoor pool, pool umbrellas, sun loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
The Inn at Tacaro Estate
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
The price is SAR 1,550
SAR 1,704 total
includes taxes & fees
28 Feb - 1 Mar
The Oaks Waterfront
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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Top Chester Hotel Reviews

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"Nice pl"
Christian 1-night trip
Posted 1 day ago
SpringHill Suites by Marriott Annapolis

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. 13.4 mi (21.5 km) from the heart of Chester. Enjoy the free full breakfast and unique décor. Flag House Inn: 5 rooms. 10.6 mi (17 km) from the downtown core. Enjoy the unique décor and fireplace in the lobby. Inn at Huntingfield Creek: 12 rooms. Situated 10.1 mi (16.2 km) from the heart of Chester. Enjoy the local cuisine breakfast and jetted tubs. The Oaks Waterfront: 15 rooms. 17 mi (27.4 km) from the heart of downtown. Enjoy the free cooked breakfast and rooftop terrace. 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.
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.