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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Chesterland bed & breakfast

Property grounds
The Lost Pearl

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 AED 870
AED 914 total
includes taxes & fees
14 Dec - 15 Dec
The Lost Pearl
Exterior
The Willoughby House

The Willoughby House

The Willoughby House
3.0 star property
Willoughby
9.6 out of 10, Exceptional, (13)
"Clean rooms and comfortable beds helped us throughly enjoy our stay! "
United States
Mary
The price is AED 519
AED 598 total
includes taxes & fees
14 Dec - 15 Dec
The Willoughby House
Terrace/patio
The Caboose

The Caboose

The Caboose
Madison
9.6 out of 10, Exceptional, (5)
"So cute and the land was beautiful! Owners went above and beyond to make sure we had a wonderful stay 💜"
United States
Melissa C.
The Caboose
Outdoor dining
Urban Industrial 1BD Stay in Cleveland

Urban Industrial 1BD Stay in Cleveland

Urban Industrial 1BD Stay in Cleveland
2.0 star property
Downtown Cleveland
10.0 out of 10, Exceptional, (1)
The price is AED 258
AED 627 total
includes taxes & fees
14 Dec - 15 Dec
Urban Industrial 1BD Stay in Cleveland
Outdoor dining
Industrial Style Living in Downtown Cleveland!

Industrial Style Living in Downtown Cleveland!

Industrial Style Living in Downtown Cleveland!
Cleveland
7.4 out of 10, Good, (3)
"Loved it"
United States
Michael V.
The price is AED 258
AED 743 total
includes taxes & fees
16 Dec - 17 Dec
Industrial Style Living in Downtown Cleveland!
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

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 AED 735
AED 863 total
includes taxes & fees
14 Dec - 15 Dec
Clifford House Private Home Bed & Breakfast
Outdoor dining
Cleveland 1BR – Industrial Style Living

Cleveland 1BR – Industrial Style Living

Cleveland 1BR – Industrial Style Living
2.0 star property
Downtown Cleveland
8.4 out of 10, Very Good, (5)
"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 "
United States
Barry H.
The price is AED 258
AED 627 total
includes taxes & fees
11 Jan - 12 January 2026
Cleveland 1BR – Industrial Style Living
Outdoor dining
Industrial Townhome Style Loft in DT CLE!

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
14 Dec - 15 Dec
Industrial Townhome Style Loft in DT CLE!
Outdoor dining
Industrial Style 1BD Loft in CLE!

Industrial Style 1BD Loft in CLE!

Industrial Style 1BD Loft in CLE!
2.0 star property
Downtown Cleveland
The price is AED 147
AED 544 total
includes taxes & fees
17 Dec - 18 Dec
Industrial Style 1BD Loft in CLE!
Outdoor dining
Industrial-Style Townhome Loft in Cleveland

Industrial-Style Townhome Loft in Cleveland

Industrial-Style Townhome Loft in Cleveland
2.0 star property
Downtown Cleveland
The price is AED 258
AED 664 total
includes taxes & fees
11 Jan - 12 January 2026
Industrial-Style Townhome Loft in Cleveland
Outdoor dining
Chic & Cozy 2BD Stay in Downtown

Chic & Cozy 2BD Stay in Downtown

Chic & Cozy 2BD Stay in Downtown
2.0 star property
Downtown Cleveland
The price is AED 337
AED 812 total
includes taxes & fees
11 Jan - 12 January 2026
Chic & Cozy 2BD Stay in Downtown
Outdoor dining
Industrial 1BD Apt in the Heart of the City

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)
The price is AED 258
AED 629 total
includes taxes & fees
11 Jan - 12 January 2026
Industrial 1BD Apt in the Heart of the City
Outdoor dining
Stylish Industrial 1BD Apartment – Cleveland

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 627 total
includes taxes & fees
11 Jan - 12 January 2026
Stylish Industrial 1BD Apartment – Cleveland
Outdoor dining
Stylish 1BD Apt in the Heart of City

Stylish 1BD Apt in the Heart of City

Stylish 1BD Apt in the Heart of City
2.0 star property
Downtown Cleveland
The price is AED 258
AED 627 total
includes taxes & fees
11 Jan - 12 January 2026
Stylish 1BD Apt in the Heart of City
Outdoor dining
Industrial-Chic 1BR in Central Cleveland

Industrial-Chic 1BR in Central Cleveland

Industrial-Chic 1BR in Central Cleveland
2.0 star property
Downtown Cleveland
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. "
United States
Brooke F.
The price is AED 258
AED 627 total
includes taxes & fees
11 Jan - 12 January 2026
Industrial-Chic 1BR in Central Cleveland
Outdoor dining
1bd Modern Loft in DT Cleveland

1bd Modern Loft in DT Cleveland

1bd Modern Loft in DT Cleveland
Downtown 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. "
United States
andrew
The price is AED 258
AED 627 total
includes taxes & fees
11 Jan - 12 January 2026
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.
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Top Chesterland Hotel Reviews

Hilton Garden Inn Cleveland East/Mayfield Village

Hilton Garden Inn Cleveland East/Mayfield Village

10/10 Excellent
"Yes"
Osamwonyi Eden 1-night trip
Posted 19 hours ago
Hilton Garden Inn Cleveland East/Mayfield Village

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?
Check out this B&B in the area: The Willoughby House: 10 rooms. 8.6 mi (13.9 km) from the downtown core. Enjoy the onsite dining and bar/lounge.
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.