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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

B&B in Chester

Lake
Inn at Huntingfield Creek
Inn at Huntingfield Creek
3.5 star property
10.0 out of 10, Exceptional, (56)
"We stayed one night for our Anniversary, and the stay was so peaceful. The grounds are beautiful, the staff so nice, and the main house is amazing. We definitely plan on making this an annual thing!"
United States
Aaron
Inn at Huntingfield Creek
Exterior
George Brooks House B&B
George Brooks House B&B
3.0 star property
8.6 out of 10, Excellent, (64)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is AED 661
AED 727 total
includes taxes & fees
27 Oct - 28 Oct
George Brooks House B&B
Porch
Parsonage Inn
Parsonage Inn
3.5 star property
9.2 out of 10, Wonderful, (130)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
United States
John
The price is AED 841
AED 925 total
includes taxes & fees
27 Oct - 28 Oct
Parsonage Inn
Front of property
The Oaks Waterfront
The Oaks Waterfront
4.0 star property
10.0 out of 10, Exceptional, (39)
"This was one of the nicest hotels I've stayed at. The property was absolutely beautiful. The public and guest rooms were immaculate and nicely decorated. All staff went out of their way to be helpful and make you feel welcome. We had breakfast and dinner in the restaurant and the food was phenomenal, and the beautiful view of the water was a bonus."
United States
Deborah
The price is AED 1,517
AED 1,669 total
includes taxes & fees
27 Oct - 28 Oct
The Oaks Waterfront
Porch
Hummingbird Inn
Hummingbird Inn
3.5 star property
10.0 out of 10, Exceptional, (83)
"Our 2nd time here to spend our Anniversary. Lovely locale. Eric is a wonderful host and marvelous chef. We're thinkimg of returing for a 3rd visit next October. Birdie is a treasure too. All Inns should have dogs! :-)"
United States
Brenda
Hummingbird Inn
Beach nearby
Inn at Horn Point
Inn at Horn Point
3.0 star property
9.6 out of 10, Exceptional, (21)
"Family owned with care and pride. Excellent food and recommendations for other restaurants and activities. "
United States
Andrew
The price is AED 1,244
AED 1,419 total
includes taxes & fees
27 Oct - 28 Oct
Inn at Horn Point
Front of property
Flag House Inn
Flag House Inn
3.5 star property
9.4 out of 10, Exceptional, (79)
"Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!"
United States
Linda
The price is AED 672
AED 766 total
includes taxes & fees
2 Nov - 3 Nov
Flag House Inn
Horseback riding
The Inn at Tacaro Estate
The Inn at Tacaro Estate
5.0 star property
9.2 out of 10, Wonderful, (10)
"Amazing hospitality "
United States
Gary
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

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

10/10 Excellent
"Great having the kitchen set-up so I didn't have to dine out during my stay. Very clean, room, bed was comfortable, front desk staff friendly and helpful. Convenient location."
Carolyn 2-night trip
Posted 1 day ago
Candlewood Suites Annapolis by IHG

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: Inn at Haven Harbour: 24 rooms. 11.6 mi (18.7 km) from the heart of Chester. Enjoy the onsite dining and outdoor pool. The Oaks Waterfront: 15 rooms. 17 mi (27.4 km) from the downtown core. Enjoy the free cooked breakfast and rooftop terrace. George Brooks House B&B: 6 rooms. Situated 12.7 mi (20.5 km) from the heart of Chester. Enjoy the library and fireplace in the lobby. Hummingbird Inn: 6 rooms. 18.2 mi (29.2 km) from the heart of downtown. Enjoy the free full breakfast and massage services. Parsonage Inn: 8 rooms. Located 13.3 mi (21.4 km) from the core of Chester. Enjoy the free full breakfast and unique décor.
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.