Photo by Kristin DePlatchett

Search B&B in Chesterland

    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
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sep - 7 Sep
In two months
3 Oct - 5 Oct

Browse Select Chesterland B&B

The Willoughby House
Terrace/patio

The Willoughby House

3.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful property. Nice location. Excellent lounge & restaurant."
The price is ฿6,810
฿7,848 total
includes taxes & fees
11 Aug - 12 Aug
The Willoughby House
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 Lost Pearl
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, (66)
"Charming 100year(ish) home in Cleveland’s bustling Ohio City neighborhood. Easy walk to bars and restaurants. Friendly host and outstanding breakfasts!!"
The price is ฿6,241
฿6,834 total
includes taxes & fees
11 Aug - 12 Aug
Clifford House Private Home Bed & Breakfast
Homestead House B&B
Front of property

Homestead House B&B

4.0 star property
10.0 out of 10, Exceptional, (58)
"Beautiful B&B, fantastic breakfasts, quiet, comfy rooms!!"
Homestead House B&B
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 Chesterland Hotel Reviews

Fidelity Hotel

Fidelity Hotel

10/10 Excellent
"Lovely stay!"
Saemi 1-night trip
Posted 17 hours ago
Fidelity Hotel

Frequently asked questions

Searching for B&Bs in Chesterland?
Whether you're on a romantic holiday and want to stay somewhere quiet, or you're a solo traveller hoping to make some connections, B&Bs can be a great choice for many travellers. 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 interested in an apartment instead of a traditional hotel?
Every B&B has a unique charm — whether it's a comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the tiny details are what make bed and breakfasts the perfect escape.
What are the top B&Bs in Chesterland?
Take a look at this B&B in the area: The Willoughby House: 10 rooms. 8.6 mi (13.9 km) from the heart of Chesterland. Enjoy the on-site dining and bar/lounge.
When is the best time to book my B&B in Chesterland?
When you're planning your stay in Chesterland, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Chesterland are January, November, December and March, with each month seeing an average of 17 cm 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 should put Chester Town Hall and West Geauga Plaza on your list if you want to see more of the area.
How can I get to and around Chesterland?
You can plan your excursions 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 heart of the city. 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 to rent a car for your trip.