Photo by Patricia Knorr

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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

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, (30)
" Beautiful property, wonderful staff, excellent food service."
The price is SAR 1,550
SAR 1,705 total
includes taxes & fees
11 May - 12 May
The Oaks Waterfront
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 SAR 825
SAR 908 total
includes taxes & fees
30 Apr - 1 May
Parsonage Inn
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.6 out of 10, Excellent, (57)
"Very nice property, cozy and clean rooms, excellent service."
The price is SAR 863
SAR 949 total
includes taxes & fees
29 Apr - 30 Apr
George Brooks House B&B
The Inn at Tacaro Estate
Horseback riding

The Inn at Tacaro Estate

5.0 star property
8.8 out of 10, Excellent, (6)
"Amazing hospitality "
The price is SAR 1,186
SAR 1,352 total
includes taxes & fees
30 Apr - 1 May
The Inn at Tacaro Estate
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, (69)
"Wonderfully friendly staff, great location, and beautiful property "
The price is SAR 1,047
SAR 1,193 total
includes taxes & fees
29 Apr - 30 Apr
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 SAR 1,174
SAR 1,292 total
includes taxes & fees
29 Apr - 30 Apr
Hummingbird Inn
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 SAR 668
SAR 741 total
includes taxes & fees
4 May - 5 May
Inn at Huntingfield Creek
Robert Morris Inn
Boating

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 SAR 1,460
SAR 1,664 total
includes taxes & fees
29 Apr - 30 Apr
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
View from property

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!"
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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Other property types in Chester

Waterfront Sunset Bayview: sleeps 6
Beach

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (14)
"Loved the location, the property, and amenities. Would definitely stay again!"
Waterfront Sunset Bayview: sleeps 6
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (213)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (53)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes
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.

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. 13.3 mi (21.4 km) from the downtown core. 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.