Photo by Kristin DePlatchett

Search B&B in Chesterland

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
17 Oct - 19 Oct
In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec

B&B in Chesterland

The Lost Pearl
Property grounds

The Lost Pearl

3.5 star property
9.8 out of 10, Exceptional, (44)
"It was a wonderful relaxing time spent there!! We were treated very well and the breakfast was delicious!! Definitely plan on going back!!"
The price is SAR 694
SAR 729 total
includes taxes & fees
23 Oct - 24 Oct
The Lost Pearl
The Willoughby House
Terrace/patio

The Willoughby House

3.0 star property
9.6 out of 10, Exceptional, (9)
"Clean rooms and comfortable beds helped us throughly enjoy our stay! "
The price is SAR 733
SAR 845 total
includes taxes & fees
5 Nov - 6 Nov
The Willoughby House
Cleveland 1BR – Industrial Style Living
Interior

Cleveland 1BR – Industrial Style Living

2.0 star property
8.0 out of 10, Very Good, (4)
"The facility it’s is very nice. Getting to the place is not in the best area but no one bothers you and for the most part are pretty friendly "
The price is SAR 263
SAR 641 total
includes taxes & fees
13 Oct - 14 Oct
Cleveland 1BR – Industrial Style Living
Industrial Style Living in Downtown Cleveland!
Interior

Industrial Style Living in Downtown Cleveland!

7.4 out of 10, Good, (3)
"Loved it"
The price is SAR 263
SAR 759 total
includes taxes & fees
12 Oct - 13 Oct
Industrial Style Living in Downtown Cleveland!
Clifford House Private Home Bed & Breakfast
Superior Apartment, 1 Bedroom, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV

Clifford House Private Home Bed & Breakfast

3.0 star property
9.4 out of 10, Exceptional, (67)
"The host was amazing, knowledgeable about the area , and made a delicious breakfast! Highly recommend "
The price is SAR 728
SAR 855 total
includes taxes & fees
13 Oct - 14 Oct
Clifford House Private Home Bed & Breakfast
Modern 2BR Gem in the City’s Heart
Interior

Modern 2BR Gem in the City’s Heart

2.0 star property
7.6 out of 10, Good, (8)
"Very nice accommodations, comfy bed and recommend the Green Goat restaurant on the first floor. "
The price is SAR 344
SAR 822 total
includes taxes & fees
15 Oct - 16 Oct
Modern 2BR Gem in the City’s Heart
Industrial Townhome Style Loft in DT CLE!
View from property

Industrial Townhome Style Loft in DT CLE!

The price is SAR 263
SAR 767 total
includes taxes & fees
16 Oct - 17 Oct
Industrial Townhome Style Loft in DT CLE!
Urban Industrial 1BD Stay in Cleveland
Interior

Urban Industrial 1BD Stay in Cleveland

2.0 star property
The price is SAR 263
SAR 641 total
includes taxes & fees
23 Oct - 24 Oct
Urban Industrial 1BD Stay in Cleveland
Industrial-Chic 1BR in Central Cleveland
Interior

Industrial-Chic 1BR in Central Cleveland

2.0 star property
6.8 out of 10, (3)
"It was good proximity to everything. Parking was ok but had a lot to carry to and from car. It was very empty in the BNB. Could have used a rug or two. The futon was very hard and not comfy. The pillows were flat and only one blanket in the whole place. With the concrete it was kind of dirty on the floor. Nothing to make it cozy. Host did respond in a timely manner. Overall it worked for the occasion. "
The price is SAR 263
SAR 641 total
includes taxes & fees
12 Oct - 13 Oct
Industrial-Chic 1BR in Central Cleveland
Industrial 1BD Apt in the Heart of the City
Interior

Industrial 1BD Apt in the Heart of the City

8.0 out of 10, Very Good, (1)
The price is SAR 263
SAR 643 total
includes taxes & fees
12 Oct - 13 Oct
Industrial 1BD Apt in the Heart of the City
Stylish Industrial 1BD Apartment – Cleveland
Interior

Stylish Industrial 1BD Apartment – Cleveland

"The property was within walking distance of Progressive field, which was the reason for my stay. "
The price is SAR 263
SAR 641 total
includes taxes & fees
14 Oct - 15 Oct
Stylish Industrial 1BD Apartment – Cleveland
1bd Modern Loft in DT Cleveland
Interior

1bd Modern Loft in DT Cleveland

5.2 out of 10, (5)
"Pretty nice place, bring your own pillow for god sake pillows provided were flatter then the Olsen twins, there was a whole finger nail in the middle of the floor and a broken glass in the cabinet. Other than that nice place. "
The price is SAR 263
SAR 641 total
includes taxes & fees
12 Oct - 13 Oct
1bd Modern Loft in DT Cleveland
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterland Hotel Reviews

Fidelity Hotel

Fidelity Hotel

10/10 Excellent
"Everything was awesome! Staff was great, helpful and very friendly. Room was beautiful. Nice being close to everything we wanted to do. "
Aaron 1-night trip
Posted 1 day ago
Fidelity Hotel

Frequently asked questions

Searching for B&Bs in Chesterland?
Whether you're traveling with your family and want a friendly place to stay, or you're a solo traveler hoping to make some connections, B&Bs can be a great choice for many types of vacationers. If you're looking to play some golf while in Chesterland, you can perfect your swing at Berkshire Hill Golf Course and Fowler's Mill Golf Course.
Are you thinking about a B&B instead of a traditional hotel?
Every B&B has its own unique feel. Whether it's a comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the small details are what make bed and breakfasts a home away from home.
What are the top B&Bs in Chesterland?
Below is a B&B in the area: The Willoughby House: 10 rooms. 8.6 mi (13.9 km) from the heart of Chesterland. Enjoy the bar/lounge and onsite dining.
When is the best time to book my B&B in Chesterland?
When you're planning your stay in Chesterland, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Chesterland are January, November, December, and March, with each month seeing an average of 7 inches of snowfall.
What is there to do in Chesterland?
Spend some time exploring Chagrin River and Chesterland City Park if you're hoping to see some of the area's natural features. You might put Alpine Valley and Chester Town Hall on your list if you want to see more of the area.
How can I get to and around Chesterland?
You can map out your trip in and around Chesterland ahead of time with these transportation options. Fly into Cleveland, OH (CGF-Cuyahoga County), which is located 8.6 mi (13.8 km) from the city center. Otherwise, look for flights into Cleveland, OH (BKL-Burke Lakefront), which is 17.7 mi (28.5 km) away. If you'd like to explore around the area, you may want a rental car for your journey.