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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 11 B&B in Chester with updated reviews, rates, and availability.

The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (31)
" Beautiful property, wonderful staff, excellent food service."
The price is AED 1,517
AED 1,669 total
includes taxes & fees
22 Jun - 23 Jun
The Oaks Waterfront
The Inn at Tacaro Estate
Horseback riding

The Inn at Tacaro Estate

5.0 star property
9.0 out of 10, Wonderful, (7)
"Amazing hospitality "
The price is AED 1,753
AED 1,998 total
includes taxes & fees
5 Jun - 6 Jun
The Inn at Tacaro Estate
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (128)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is AED 955
AED 1,050 total
includes taxes & fees
9 Jun - 10 Jun
Parsonage Inn
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.6 out of 10, Excellent, (58)
"Very nice property, cozy and clean rooms, excellent service."
The price is AED 992
AED 1,091 total
includes taxes & fees
2 Jun - 3 Jun
George Brooks House B&B
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (50)
"Lovely property with wonderful owners and staff, including three very welcoming dogs. We had a perfect weekend getaway."
The price is AED 654
AED 726 total
includes taxes & fees
1 Jun - 2 Jun
Inn at Huntingfield Creek
Flag House Inn
Chesapeake Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (70)
"Wonderfully friendly staff, great location, and beautiful property "
The price is AED 1,025
AED 1,168 total
includes taxes & fees
1 Jun - 2 Jun
Flag House Inn
Hummingbird Inn
Porch

Hummingbird Inn

3.5 star property
10.0 out of 10, Exceptional, (74)
"Very hospitable staff."
The price is AED 1,150
AED 1,265 total
includes taxes & fees
1 Jun - 2 Jun
Hummingbird Inn
Robert Morris Inn
Front of property

Robert Morris Inn

3.0 star property
8.4 out of 10, Very Good, (279)
"We enjoyed our stay."
Robert Morris Inn
Inn at Horn Point
Beach nearby

Inn at Horn Point

3.0 star property
9.4 out of 10, Exceptional, (19)
"This B&B was centrally located, clean,safe and quiet. However, even though I knew there would be no breakfast, I thought that like most B&B’s there would be the possibility of coffee or tea in the morning. There was no one home to welcome us or give information about nearby restaurants, etc. Why take the reservation if you can’t provide the amenities most B&B’s feature?"
The price is AED 1,288
AED 1,469 total
includes taxes & fees
1 Jun - 2 Jun
Inn at Horn Point
Black Walnut Point Inn
Outdoor pool

Black Walnut Point Inn

3.5 star property
9.0 out of 10, Wonderful, (55)
"Wife and I stayed 3 days for 41st anniversary. Bob and Tracy are wonderful hosts. "
Black Walnut Point Inn
Laurel Grove Inn on the South
Interior detail

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (513)
"Now I understand why the great ratings! What a wonderful place to stay. Beautiful views, comfortable with all the conveniences of home. Great hosts who go above and beyond to ensure your stay is fabulous. We will definitely return!"
The price is AED 661
AED 754 total
includes taxes & fees
1 Jul - 2 Jul
Laurel Grove Inn on the South
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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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: The Oaks Waterfront: 15 rooms. 17 mi (27.4 km) from the heart of Chester. Enjoy the free cooked breakfast and rooftop terrace. Parsonage Inn: 8 rooms. Situated 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 heart of downtown. Enjoy the library and fireplace in the lobby. Inn at Huntingfield Creek: 12 rooms. Located 10.1 mi (16.2 km) from the core of Chester. Enjoy the jetted tubs and spa.
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.
What is there to do in Chester?
Spend some time exploring Eastern Neck National Wildlife Refuge and Sandy Point Beach if you’re hoping to see some of the area’s natural features. You might put Queenstown Premium Outlets and Sandy Point State Park on your list if you want to see more of the area.
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.