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Compare 7 B&B in Chester with updated reviews, rates, and availability.

Ragland Mansion Bed & Breakfast
Living area

Ragland Mansion Bed & Breakfast

3.5 star property
9.8 out of 10, Exceptional, (328)
"Excellent choice for 1 night or a weekend get away…"
Ragland Mansion Bed & Breakfast
The Boulevard Inn
Front of property

The Boulevard Inn

4.0 star property
9.8 out of 10, Exceptional, (39)
" Beaultiful and spacious rooms. Wonderful hosts. Walking distance to many restaurants and attractions. Parking onsite. "
The price is SAR 1,149
SAR 1,310 total
includes taxes & fees
7 Jan - 8 January 2025
The Boulevard Inn
A house full of steel balls and games
Front of property

A house full of steel balls and games

2.5 star property
9.6 out of 10, Exceptional, (85)
"I stay here every time I come to Richmond for business. It always feels like I'm coming home."
The price is SAR 379
SAR 488 total
includes taxes & fees
1 Jan - 2 January 2025
A house full of steel balls and games
Rent the Entire Historic Vaiden Inn on 8 acres
Main entrance to Vaiden Inn

Rent the Entire Historic Vaiden Inn on 8 acres

10.0 out of 10, Exceptional, (36)
"Vaiden Inn is a very comfortable place to stay. The property is beautiful and the hosts are very communicative and gracious. Coming in the fall afforded us some beautiful foliage on our way to Williamsburg. Although the kitchenette is small, it was well appointed. The bedrooms were gorgeous and the beds were so comfortable. Thank you for a wonderful stay! "
Rent the Entire Historic Vaiden Inn on 8 acres
Gracefield Hall B&B
Porch

Gracefield Hall B&B

3.0 star property
10.0 out of 10, Exceptional, (60)
"We LOVED Gracefield Hall for many reasons: 1) the hosts were warm and accommodating and did everything they could to make our visit perfect. (Including loaning a jacket to one member of our party who planned poorly.) 2) The house itself is an historic masterpiece and the stories behind it are great. 3) Gracefield Hall is close to all three of southeast Virginia's hallmark historic sites, but is located in a calm and quiet part of the state. 4) The breakfast is indescribably delicious --...
The price is SAR 695
SAR 751 total
includes taxes & fees
2 Jan - 3 January 2025
Gracefield Hall B&B
Cozy Suburban Nest Guest Suite separate from main home with hottub
Upstairs hallway

Cozy Suburban Nest Guest Suite separate from main home with hottub

8.8 out of 10, Excellent, (6)
"We have 2 dogs and needed a place for one night. The place was super cute. However, the stairs were very steep. This was mentioned in a review,s so I was prepared. But they are VERY steep, and it was difficult for the dogs to get up/down them. The twin bed's mattress very uncomfortable, but the other one was fine"
The price is SAR 413
SAR 671 total
includes taxes & fees
6 Jan - 7 January 2025
Cozy Suburban Nest Guest Suite separate from main home with hottub
Vaiden Inn c. 1781 - 4 bedrooms, kitchenette, parlor, living/dining, 8+ acres
West entrance with porch swing

Vaiden Inn c. 1781 - 4 bedrooms, kitchenette, parlor, living/dining, 8+ acres

10.0 out of 10, Exceptional, (29)
"We were so lucky to find this amazing property! The pictures don’t do it justice. Beds were extremely comfortable, house was very clean and well maintained. All bedrooms had well-appointed bathrooms. While we were there due to emergency repairs to our home, this would be an amazing place for a bridal party. "
Vaiden Inn c. 1781 - 4 bedrooms, kitchenette, parlor, living/dining, 8+ acres
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

Recline at Timberline! Family friendly!
Large dining rom

Recline at Timberline! Family friendly!

9.4 out of 10, Exceptional, (35)
"The house is very cozy. The kitchen was clean and well stocked. There are Roku TVs in the living room and bedroom. Nice backyard with a swing set if you have kids. There were bowls for pets in the downstairs closet. "
Recline at Timberline! Family friendly!
Downtown Living in Historic Richmond Loft
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Downtown Living in Historic Richmond Loft

8.4 out of 10, Very Good, (48)
"Good place."
The price is SAR 588
SAR 1,186 total
includes taxes & fees
1 Jan - 2 January 2025
Downtown Living in Historic Richmond Loft
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
The GiaMaria resting in only 4 feet of water and a beautiful oxbow on the James.

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

9.6 out of 10, Exceptional, (203)
"Captain Ron is my favorite host so far! He met me at the dock on the cold dark pouring rain, to make sure I got aboard and was comfortable. And the next day, kept me posted on the tide situation. He was helpful in every way possible. The boat is comfortable and welcoming. It is quiet and the water is calm. It is close enough to go do things, but secluded enough to feel like you’re a million miles away from every day life. I definitely will stay again, and I’ve already recommended it to...
The price is SAR 376
SAR 766 total
includes taxes & fees
1 Jan - 2 January 2025
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
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 traveling with your family and want a friendly place to stay, or you’re traveling solo and hoping to get some tips from locals, a B&B can be a good choice for many different types of travelers. If your ideal vacation to Chester includes spending lots of time outside, Henricus Historical Park and Parker’s Battery Park are good spots to enjoy the scenery.
Why consider a B&B over a traditional hotel room?
With attentive service, opportunities to meet other guests, and delectable breakfasts, B&Bs provide a truly one-of-a-kind environment.
What are the top B&Bs in Chester?
Below are some B&Bs in the surrounding area: Ragland Mansion Bed & Breakfast: 8 rooms. 9.4 mi (15.1 km) from the heart of Chester. Enjoy the free cooked breakfast and unique décor. A house full of steel balls and games: 3 rooms. 17 mi (27.4 km) from the downtown core. Enjoy the private yard and unique décor. The Boulevard Inn: 5 rooms. Situated 13.6 mi (22 km) from the heart of Chester. Enjoy the free full breakfast and designer toiletries.
When is the best time to stay at a B&B in Chester?
When you’re dreaming of a 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 76°F, while the coldest months are January and February with an average of 43°F. Average annual precipitation for Chester is 50 inches.
What is there to do in Chester?
Travelers enjoy Chester for its restaurants and shopping. If you’re looking to find something to do during your travels, you might consider checking out Iron Bridge Sports Park and The Lazy Daisy. You might put James River and Henricus Historical Park on your list if you want to see more of the area.
How can I get to and around Chester?
Mapping out your trip in and around Chester is easy with these transportation options. Fly into Richmond Intl. Airport (RIC), which is located 12.2 mi (19.6 km) from the city center. If you’d like to venture out around the area, you may want to rent a car for your trip.