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Search B&B in Chesterland

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Our top choices for Chesterland bed & breakfast

The Willoughby House

The Willoughby House
3.0 star property
Willoughby
9.4 out of 10, Exceptional, (16)
"Clean rooms and comfortable beds helped us throughly enjoy our stay! "
United States
Mary
The price is ฿4,817
฿5,551 total
includes taxes & fees
29 Dec - 30 Dec
The Willoughby House

The Lost Pearl

The Lost Pearl
3.5 star property
Madison
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!!"
United States
Jarrod
The price is ฿7,355
฿7,723 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Lost Pearl

Clifford House Private Home Bed & Breakfast

Clifford House Private Home Bed & Breakfast
3.0 star property
Ohio City
9.4 out of 10, Exceptional, (70)
"The host was amazing, knowledgeable about the area , and made a delicious breakfast! Highly recommend "
United States
Jennifer
The price is ฿6,207
฿7,293 total
includes taxes & fees
5 Jan - 6 Jan 2026
Clifford House Private Home Bed & Breakfast
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 Chesterland Hotel Reviews

Find out more about Chesterland

Chesterland B&B information

Number of reviews
128
Accommodation
4 B&B
Lowest Price
฿5,551
Highest Price
฿7,723

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 Fowler's Mill Golf Course and Berkshire Hill 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 bar/lounge and on-site dining.
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 Fowler's Mill Golf Course and Alpine Valley 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.

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