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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

B&B in Chester

The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (32)
" Beautiful property, wonderful staff, excellent food service."
The price is AED 1,517
AED 1,669 total
includes taxes & fees
20 Jul - 21 Jul
The Oaks Waterfront
Laurel Grove Inn on the South
Outdoor dining

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (516)
"Beautiful property and lovely hosts."
The price is AED 661
AED 754 total
includes taxes & fees
17 Aug - 18 Aug
Laurel Grove Inn on the South
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.8 out of 10, Excellent, (61)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is AED 893
AED 982 total
includes taxes & fees
21 Jul - 22 Jul
George Brooks House B&B
Flag House Inn
Front of property

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (72)
"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!"
The price is AED 640
AED 730 total
includes taxes & fees
22 Jul - 23 Jul
Flag House Inn
The Inn at Tacaro Estate
Horseback riding

The Inn at Tacaro Estate

5.0 star property
9.2 out of 10, Wonderful, (9)
"1940’s estate is maintained to remind you of those times. There was a “Speak-EZ” in the basement they had open Friday and Saturday evenings. My room was spacious and included a balcony. Huge front lawn with a pool and a view to the Bay. "
The Inn at Tacaro Estate
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (52)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
Inn at Huntingfield Creek
Hummingbird Inn
Porch

Hummingbird Inn

3.5 star property
10.0 out of 10, Exceptional, (76)
"Hummingbird Inn is so gracious to all guests. I was there for a triathlon and Eric and Mary made sure I was taken care of to race! Love this Inn!"
Hummingbird Inn
Inn at Horn Point
Beach nearby

Inn at Horn Point

3.0 star property
9.4 out of 10, Exceptional, (19)
"Family owned with care and pride. Excellent food and recommendations for other restaurants and activities. "
The price is AED 1,263
AED 1,440 total
includes taxes & fees
4 Aug - 5 Aug
Inn at Horn Point
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
21 Jul - 22 Jul
Parsonage Inn
Robert Morris Inn
Pool

Robert Morris Inn

3.0 star property
8.4 out of 10, Very Good, (279)
"Lovely historic building with amazing food and fun old books and art. "
Robert Morris Inn
Black Walnut Point Inn
Outdoor pool

Black Walnut Point Inn

3.5 star property
9.0 out of 10, Wonderful, (56)
"Wife and I stayed 3 days for 41st anniversary. Bob and Tracy are wonderful hosts. "
Black Walnut Point Inn
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
The price is AED 902
AED 1,075 total
includes taxes & fees
20 Jul - 21 Jul
Inn at Haven Harbour
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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Great room for a great price... Very friendly staff, too."
Steven 2-night trip
Posted 23 hours ago
Sonesta ES Suites 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: The Oaks Waterfront: 15 rooms. 17 mi (27.4 km) from the heart of Chester. Enjoy the free cooked breakfast and rooftop terrace. Laurel Grove Inn on the South: 5 rooms. 15.8 mi (25.4 km) from the downtown core. Enjoy the deli and arcade game room. Flag House Inn: 5 rooms. Situated 10.6 mi (17 km) from the heart of Chester. Enjoy the local cuisine 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.
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.