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
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

B&B in Chesterland

1bd Modern Loft in DT Cleveland
Interior

1bd Modern Loft in DT Cleveland

8.0 out of 10, Very Good, (1)
"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. "
The price is AED 258
AED 627 total
includes taxes & fees
16 Jul - 17 Jul
1bd Modern Loft in DT Cleveland
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 AED 709
AED 776 total
includes taxes & fees
21 Jul - 22 Jul
Clifford House Private Home Bed & Breakfast
Industrial 1BD Apt in the Heart of the City
Interior

Industrial 1BD Apt in the Heart of the City

The price is AED 258
AED 629 total
includes taxes & fees
28 Jul - 29 Jul
Industrial 1BD Apt in the Heart of the City
1BD Modern Industrial Loft in DT Cleveland
Interior

1BD Modern Industrial Loft in DT Cleveland

2.0 star property
7.6 out of 10, Good, (4)
"Stay was nice. Nice quit place to just relax. Keep this place in mind for next time. "
The price is AED 258
AED 627 total
includes taxes & fees
15 Jul - 16 Jul
1BD Modern Industrial Loft in DT Cleveland
Industrial 1BD Chic close to Cavs & Browns
Interior

Industrial 1BD Chic close to Cavs & Browns

2.0 star property
8.0 out of 10, Very Good, (1)
"Minor issue with lock but otherwise a nice stay!"
The price is AED 258
AED 627 total
includes taxes & fees
15 Jul - 16 Jul
Industrial 1BD Chic close to Cavs & Browns
Industrial Style Living in Downtown Cleveland!
Interior

Industrial Style Living in Downtown Cleveland!

The price is AED 258
AED 751 total
includes taxes & fees
28 Jul - 29 Jul
Industrial Style Living in Downtown Cleveland!
Trendy Modern 1BD Industrial Loft in DT Cleveland
Interior

Trendy Modern 1BD Industrial Loft in DT Cleveland

2.0 star property
6.0 out of 10, (1)
"First they should advertise free parking with this unit, that's a plus. The bad side: They never reached out with the code to get in, I had to call. They gave us the wrong address. They gave us the wrong code to get in the building. The door to the unit had dead batteries and we had to wait 45 minutes for someone to let us in. The pillows were flat. The towels were small and cheap."
The price is AED 258
AED 627 total
includes taxes & fees
15 Jul - 16 Jul
Trendy Modern 1BD Industrial Loft in DT Cleveland
Chic Industrial style 1BD living in Cleveland!
Interior

Chic Industrial style 1BD living in Cleveland!

2.0 star property
The price is AED 258
AED 627 total
includes taxes & fees
20 Jul - 21 Jul
Chic Industrial style 1BD living in Cleveland!
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
Industrial Townhome Style Loft in DT CLE!
View from property

Industrial Townhome Style Loft in DT CLE!

The price is AED 258
AED 743 total
includes taxes & fees
15 Jul - 16 Jul
Industrial Townhome Style Loft in DT CLE!
1BD Chic Loft in DT Cleveland!
Interior

1BD Chic Loft in DT Cleveland!

2.0 star property
The price is AED 258
AED 627 total
includes taxes & fees
15 Jul - 16 Jul
1BD Chic Loft in DT Cleveland!
The Caboose
Property grounds

The Caboose

9.4 out of 10, Exceptional, (3)
"So cute and the land was beautiful! Owners went above and beyond to make sure we had a wonderful stay 💜"
The price is AED 579
AED 1,030 total
includes taxes & fees
25 Jul - 26 Jul
The Caboose
Cozy 1BD Apt in DT Cleveland
Interior

Cozy 1BD Apt in DT Cleveland

2.0 star property
The price is AED 258
AED 627 total
includes taxes & fees
20 Jul - 21 Jul
Cozy 1BD Apt in DT Cleveland
The Willoughby House
Terrace/patio

The Willoughby House

3.0 star property
The price is AED 859
AED 991 total
includes taxes & fees
15 Jul - 16 Jul
The Willoughby House
Industrial 1BD in DT Cleveland
Interior

Industrial 1BD in DT Cleveland

2.0 star property
The price is AED 258
AED 627 total
includes taxes & fees
11 Aug - 12 Aug
Industrial 1BD in DT Cleveland
Industrial Style Living in Downtown CLE!
Interior

Industrial Style Living in Downtown CLE!

2.0 star property
Industrial Style Living in Downtown CLE!
Cozy 2BD Apartment in the Heart of the City
Interior

Cozy 2BD Apartment in the Heart of the City

2.0 star property
Cozy 2BD Apartment in the Heart of the City
Vibrant 1bd in Downtown Cleveland!
Interior

Vibrant 1bd in Downtown Cleveland!

2.0 star property
Vibrant 1bd in Downtown Cleveland!
Industrial 1BD Apt in Downtown Cleveland
Interior

Industrial 1BD Apt in Downtown Cleveland

2.0 star property
Industrial 1BD Apt in Downtown 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 are some well-liked B&Bs in the surrounding area: Studio Loft in Downtown Cleveland!: 17.6 mi (28.4 km) from the heart of Chesterland.1bd Modern Loft in DT Cleveland: 17.6 mi (28.4 km) from the downtown core. Industrial 2BD Apt in Downtown Cleveland!: Situated 17.6 mi (28.4 km) from the heart of Chesterland.
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.