Find a Bed and Breakfast in Chester from CA $98

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Chester B&B

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, (92)
"Great place to stay. Pete is a great host, easy check in great communication, pinball machines and games in the rooms really great. Quick drive to some good dining."
The price is CA $98
CA $132 total
includes taxes & fees
Aug 31 - Sep 1
A house full of steel balls and games
Ragland Mansion Bed & Breakfast
Front of property

Ragland Mansion Bed & Breakfast

3.5 star property
9.8 out of 10, Exceptional, (349)
"This historic property is a great place to share time with family and friends before Amtrak trip the next morning . Convenient to Old Town restaurants. We were welcomed and truly enjoyed the individual attention. The whole experience was perfect."
The price is CA $158
CA $213 total
includes taxes & fees
Sep 3 - Sep 4
Ragland Mansion Bed & Breakfast
The Boulevard Inn
Terrace/patio

The Boulevard Inn

4.0 star property
9.8 out of 10, Exceptional, (56)
"What a lovely gem of a boutique inn! Conveniently located to shops, restaurants, the VMFA and one of the prettiest neighborhoods in Richmond. This place exudes southern hospitality and charm. Amazing wine and cheese, amazing breakfast, and just amazing all around. We will be back!"
The price is CA $387
CA $441 total
includes taxes & fees
Aug 24 - Aug 25
The Boulevard Inn
Gracefield Hall B&B
Front of property

Gracefield Hall B&B

3.0 star property
10.0 out of 10, Exceptional, (67)
"Great location for Colonial Downs racing, beautiful accommodations and your hosts, Patricia and Larry could not have done more for us."
The price is CA $255
CA $275 total
includes taxes & fees
Aug 14 - Aug 15
Gracefield Hall B&B
Historic Vaiden House, c.1781, on 8 acres: Modern Amenities with Old World Charm
Interior

Historic Vaiden House, c.1781, on 8 acres: Modern Amenities with Old World Charm

10.0 out of 10, Exceptional, (37)
"Came together with a group of friends to celebrate many things. Can’t say enough about the host and staff’s friendliness as well as maintaining a beautiful location at the Vaiden Inn. We’ll be back!!"
The price is CA $274
CA $559 total
includes taxes & fees
Sep 8 - Sep 9
Historic Vaiden House, c.1781, on 8 acres: Modern Amenities with Old World Charm
Rent the Entire Historic Vaiden Inn on 8 acres
Interior

Rent the Entire Historic Vaiden Inn on 8 acres

10.0 out of 10, Exceptional, (36)
"Lots of space, comfortable beds."
Rent the Entire Historic Vaiden Inn on 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

The Jefferson Hotel

The Jefferson Hotel

10/10 Excellent
"Concierge and transportation staff were nothing short of amazing."
April 3-night trip
Posted 5 hours ago
The Jefferson Hotel

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Chester?
Prices for B&Bs in Chester often vary, but you can find a great deal from CA $98 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Chester?
The best time to book a B&B in Chester is during the enchanting spring months of April to June. This period attracts visitors eager to immerse themselves in the rich history and vibrant culture of this charming city. With the arrival of warmer weather, the historic streets come alive, and outdoor sightseeing becomes a true pleasure.

April, in particular, is a lovely time to visit, with temperatures typically ranging from 10 to 15 degrees Celsius. The blossoming gardens and parks, like Grosvenor Park, offer a picturesque setting for leisurely strolls, and the city's famous Roman walls provide a unique vantage point to appreciate Chester's scenic beauty.

If you're looking for a more budget-friendly option, consider visiting in November. This quieter month allows for a more relaxed exploration of Chester's attractions, including the stunning Chester Cathedral and the captivating Rows. You'll find that the city's charm remains intact, with fewer crowds and the opportunity to enjoy the local shops and cafés at your own pace.
What is the difference between a Chester B&B and a hotel?
Every Chester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chester B&Bs.