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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

B&B in Chester

Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
8.0 out of 10, Very Good, (3)
"Steps to the 3rd floor attic Low headroom every where 4' to 5' headroom in front of the toilet 8 yr old banged his head Everything was good except the very small room Don't rent this room unless you're 4' tall I'm surprised it passed inspection "
The price is NT$5,939
NT$7,259 total
includes taxes & fees
Aug 26 - Aug 27
Inn at Haven Harbour
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
Flag House Inn
Front of property

Flag House Inn

3.5 star property
9.4 out of 10, Exceptional, (76)
"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 NT$4,184
NT$4,770 total
includes taxes & fees
Aug 20 - Aug 21
Flag House Inn
Laurel Grove Inn on the South
Outdoor dining

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (519)
"Beautiful property and lovely hosts."
The price is NT$5,406
NT$6,163 total
includes taxes & fees
Sep 18 - Sep 19
Laurel Grove Inn on the South
The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (34)
"The facility designed was out standing and the staff was very good. "
The price is NT$12,391
NT$13,630 total
includes taxes & fees
Aug 28 - Aug 29
The Oaks Waterfront
Parsonage Inn
Porch

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!"
The price is NT$6,869
NT$7,556 total
includes taxes & fees
Aug 20 - Aug 21
Parsonage Inn
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 NT$6,209
NT$6,830 total
includes taxes & fees
Aug 20 - Aug 21
George Brooks House B&B
Hummingbird Inn
Porch

Hummingbird Inn

3.5 star property
10.0 out of 10, Exceptional, (77)
"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
The Inn at Tacaro Estate
Horseback riding

The Inn at Tacaro Estate

5.0 star property
9.2 out of 10, Wonderful, (9)
"Amazing hospitality "
The price is NT$10,409
NT$11,866 total
includes taxes & fees
Aug 27 - Aug 28
The Inn at Tacaro Estate
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 NT$10,313
NT$11,756 total
includes taxes & fees
Aug 20 - Aug 21
Inn at Horn Point
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

The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Great place! "
Stuart W 2-night trip
Posted 10 hours ago
The Westin 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: Flag House Inn: 5 rooms. 10.6 mi (17 km) from the heart of Chester. Enjoy the local cuisine breakfast and unique décor. The Oaks Waterfront: 15 rooms. 17 mi (27.4 km) from the downtown core. Enjoy the free cooked breakfast and rooftop terrace. Inn at Haven Harbour: 24 rooms. Situated 11.6 mi (18.7 km) from the heart of Chester. Enjoy the onsite dining and outdoor pool. Laurel Grove Inn on the South: 5 rooms. 15.8 mi (25.4 km) from the heart of downtown. Enjoy the deli and arcade game room. 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.