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Check prices for these dates

Next weekend
30 Jan - 1 Feb
In two weeks
6 Feb - 8 Feb
In one month
20 Feb - 22 Feb
In two months
20 Mar - 22 Mar

Our top choices for Chesterland bed & breakfast

Property grounds

The Lost Pearl

The Lost Pearl
3.5 star property
Madison
9.8 out of 10, Exceptional, (44 reviews)
"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 AED 830
AED 872 total
includes taxes & fees
15 Feb - 16 Feb
The Lost Pearl
Outdoor dining

Stylish Industrial 1BD Apartment – Cleveland

Stylish Industrial 1BD Apartment – Cleveland
Downtown Cleveland
"The property was within walking distance of Progressive field, which was the reason for my stay. "
United States
Ryan
The price is AED 258
AED 700 total
includes taxes & fees
16 Feb - 17 Feb
Stylish Industrial 1BD Apartment – Cleveland
Outdoor dining

Industrial Townhome Style Loft in DT CLE!

Industrial Townhome Style Loft in DT CLE!
Cleveland
The price is AED 258
AED 743 total
includes taxes & fees
26 Jan - 27 Jan
Industrial Townhome Style Loft in DT CLE!
Exterior

The Willoughby House

The Willoughby House
3.0 star property
Willoughby
9.0 out of 10, Wonderful, (19 reviews)
"Clean rooms and comfortable beds helped us throughly enjoy our stay! "
United States
Mary
The price is AED 622
AED 717 total
includes taxes & fees
26 Jan - 27 Jan
The Willoughby House
Superior Apartment, 1 Bedroom, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV

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 reviews)
"The host was amazing, knowledgeable about the area , and made a delicious breakfast! Highly recommend "
United States
Jennifer
The price is AED 713
AED 837 total
includes taxes & fees
26 Jan - 27 Jan
Clifford House Private Home Bed & Breakfast
Outdoor dining

Cleveland 1BR – Industrial Style Living

Cleveland 1BR – Industrial Style Living
Downtown Cleveland
8.4 out of 10, Very Good, (5 reviews)
"Super clean and secure location with great parking! If you are looking to catch a game or just hang out in downtown Cleveland this is the place!"
United States
Scott P.
The price is AED 258
AED 700 total
includes taxes & fees
27 Jan - 28 Jan
Cleveland 1BR – Industrial Style Living
Outdoor dining

Industrial-Style Townhome Loft in Cleveland

Industrial-Style Townhome Loft in Cleveland
Downtown Cleveland
The price is AED 258
AED 743 total
includes taxes & fees
26 Jan - 27 Jan
Industrial-Style Townhome Loft in Cleveland
Outdoor dining

Industrial Style 1BD Loft in CLE!

Industrial Style 1BD Loft in CLE!
Downtown Cleveland
The price is AED 258
AED 743 total
includes taxes & fees
26 Jan - 27 Jan
Industrial Style 1BD Loft in CLE!
Outdoor dining

Cozy Industrial Style in DT Cleveland!

Cozy Industrial Style in DT Cleveland!
Downtown Cleveland
The price is AED 258
AED 700 total
includes taxes & fees
26 Jan - 27 Jan
Cozy Industrial Style in DT Cleveland!
Outdoor dining

Stylish 1BD Apt in the Heart of City

Stylish 1BD Apt in the Heart of City
Downtown Cleveland
The price is AED 258
AED 700 total
includes taxes & fees
26 Jan - 27 Jan
Stylish 1BD Apt in the Heart of City
Outdoor dining

Industrial Style Living in Downtown Cleveland!

Industrial Style Living in Downtown Cleveland!
Cleveland
7.4 out of 10, Good, (3 reviews)
"Loved it"
United States
Michael V.
The price is AED 258
AED 743 total
includes taxes & fees
27 Jan - 28 Jan
Industrial Style Living in Downtown Cleveland!
Outdoor dining

Industrial 1BD in DT Cleveland

Industrial 1BD in DT Cleveland
Downtown Cleveland
7.4 out of 10, Good, (3 reviews)
"Great place to stay for a football game! Didn’t need much coming from Canada."
United States
Tim M.
The price is AED 258
AED 700 total
includes taxes & fees
26 Jan - 27 Jan
Industrial 1BD in DT Cleveland
Outdoor dining

Industrial 1BD Apt in the Heart of the City

Industrial 1BD Apt in the Heart of the City
Downtown Cleveland
8.0 out of 10, Very Good, (1 review)
The price is AED 258
AED 700 total
includes taxes & fees
26 Jan - 27 Jan
Industrial 1BD Apt in the Heart of the City
Outdoor dining

Chic & Cozy 2BD Stay in Downtown

Chic & Cozy 2BD Stay in Downtown
Downtown Cleveland
The price is AED 337
AED 901 total
includes taxes & fees
26 Jan - 27 Jan
Chic & Cozy 2BD Stay in Downtown
Outdoor dining

Industrial-Chic 1BR in Central Cleveland

Industrial-Chic 1BR in Central Cleveland
Downtown Cleveland
6.8 out of 10, (3 reviews)
"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. "
United States
Brooke F.
The price is AED 258
AED 700 total
includes taxes & fees
27 Jan - 28 Jan
Industrial-Chic 1BR in Central Cleveland
TV

1BD Apt in Downtown Cleveland!

1BD Apt in Downtown Cleveland!
Downtown Cleveland
The price is AED 258
AED 700 total
includes taxes & fees
26 Jan - 27 Jan
1BD Apt in Downtown Cleveland!
Outdoor dining

1bd Modern Apt in DT Cleveland

1bd Modern Apt in DT Cleveland
Downtown Cleveland
5.2 out of 10, (5 reviews)
"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. "
United States
andrew
The price is AED 258
AED 700 total
includes taxes & fees
26 Jan - 27 Jan
1bd Modern Apt 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.
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Top Chesterland Hotel Reviews

Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

10/10 Excellent
"Very nice lobby and restaurant. Room clean & beds comfortable. Shuttle to Cleveland clinic the most convenient way there especially when it’s 15 degrees out. "
Christine 3-night trip
Posted 2 days ago
Holiday Inn Cleveland Clinic by IHG

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 Fowler's Mill Golf Course and Berkshire Hill 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 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 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.