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Book Chester Bed & Breakfast

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Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
In one month
Dec 5 - Dec 7
In two months
Jan 2 - Jan 4

B&B in Chester

Lake
Inn at Huntingfield Creek

Inn at Huntingfield Creek

3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (56)
"Wonderful! Quiet and relaxing anniversary! Pool was great, dock is beautiful, room was clean, comfortable and spacious. Water bottles and cookies are such a nice touch. Breakfast was delicious. Amazing property and genuine hosts. Thank you"
United States
Cristy
$144 nightly
The price is $160
Dec 1 - Dec 2
Total with taxes and fees
Inn at Huntingfield Creek
Exterior
George Brooks House B&B

George Brooks House B&B

3.0 star property
St. Michaels
8.6 out of 10, Excellent, (65)
"We thoroughly enjoyed all aspects of our stay. The Inn is spotless and wonderfully decorated. The grounds are beautiful gardens and relaxing pool and hot tub. They even have electric vehicle charging stations. The food was absolutely delicious and the proprietors friendly while allowing for privacy"
United States
Sharon
$200 nightly
The price is $220
Nov 10 - Nov 11
Total with taxes and fees
George Brooks House B&B
Front of property
Flag House Inn

Flag House Inn

3.5 star property
Historic District
9.4 out of 10, Exceptional, (80)
"Overpriced for what it offered. $500+ for a single night at the property sans breakfast or parking. Room itself was small with no real historic flair or charm. Found a used washcloth on the floor housekeeping had overlooked. To check in during peak hours we had to call hotel staff (attending to other properties when we arrived) in order to get access to the room. If this property were about $200 less expensive, I would have zero complaints, but to spend that amount of money I expected way...
United States
Kathy
$105 nightly
The price is $119
Nov 9 - Nov 10
Total with taxes and fees
Flag House Inn
Front of property
The Oaks Waterfront

The Oaks Waterfront

4.0 star property
Easton
10.0 out of 10, Exceptional, (40)
"Loved the Oaks! Fabulous accommodations and excellent staff"
United States
Barbara
$459 nightly
The price is $505
Nov 9 - Nov 10
Total with taxes and fees
The Oaks Waterfront
Beach nearby
Inn at Horn Point

Inn at Horn Point

3.0 star property
Eastport
9.6 out of 10, Exceptional, (21)
"Great place in an awesome location. Very friendly staff. Easy street side parking."
United States
Anonymous traveler
$344 nightly
The price is $392
Nov 9 - Nov 10
Total with taxes and fees
Inn at Horn Point
Porch
Parsonage Inn

Parsonage Inn

3.5 star property
St. Michaels
9.2 out of 10, Wonderful, (130)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
$229 nightly
The price is $252
Nov 10 - Nov 11
Total with taxes and fees
Parsonage Inn
Porch
Hummingbird Inn

Hummingbird Inn

3.5 star property
Easton
10.0 out of 10, Exceptional, (85)
"Chef Eric provided excellent breakfast Very good"
United States
Paul
$313 nightly
The price is $344
Nov 9 - Nov 10
Total with taxes and fees
Hummingbird Inn
Horseback riding
The Inn at Tacaro Estate

The Inn at Tacaro Estate

5.0 star property
Tracys Landing
9.2 out of 10, Wonderful, (10)
"The place was gorgeous. Very private and peaceful. Staff was great and i will definitely go back ."
United States
Jeffrey
$315 nightly
The price is $360
Dec 1 - Dec 2
Total with taxes and fees
The Inn at Tacaro Estate
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Beautiful"
LEIGH 1-night trip
Posted 1 day ago
Historic Inns of Annapolis

Find out more about Chester

Chester B&B information

Number of reviews
485
Accommodation
12 B&B
Lowest Price
$119
Highest Price
$505

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. 13.3 mi (21.4 km) from the heart of Chester. Enjoy the free full breakfast and unique décor. 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. The Oaks Waterfront: 15 rooms. Situated 17 mi (27.4 km) from the heart of Chester. Enjoy the free cooked breakfast and rooftop terrace. Inn at Haven Harbour: 24 rooms. 11.6 mi (18.7 km) from the heart of downtown. Enjoy the onsite dining and outdoor pool. 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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