A wooden bridge over a snow-covered path in a forest.

Find a Bed and Breakfast in Chesterland from CA $343

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Check prices for these dates

Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25

Our top choices for Chesterland bed & breakfast

A white house with a gravel driveway, surrounded by lush greenery and flowering bushes.

1. The Lost Pearl

The Lost Pearl
3.5 star property
Madison
9.8 out of 10, Exceptional, (45 reviews)
"Quiet and peaceful. A beautifully restored 19th Century farmhouse, comfortable rooms, friendly hosts, and a great breakfast offered as an add-on."
United States
Jessica
The price is CA $327
CA $343 total
includes taxes & fees
Aug 31 - Sep 1
The Lost Pearl
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

Drury Plaza Hotel Cleveland Downtown

Drury Plaza Hotel Cleveland Downtown

10/10 Excellent
"they have free of everything pretty much and it was a bonus"
Savanna 1-night trip
Posted 5 hours ago
Drury Plaza Hotel Cleveland Downtown

Find out more about Chesterland

Chesterland B&B information

Number of reviews
45
Accommodation
4 B&B
Lowest Price
CA $343
Highest Price
CA $343

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?
Check out this B&B in the area: Homestead House B&B: 5 rooms. Located 8.9 mi (14.3 km) from the core of Chesterland. Enjoy the free cooked breakfast and designer toiletries.
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 Berkshire Hill Golf Course and Fowler's Mill Golf Course 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.

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