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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 34 B&B in Chesterland with updated reviews, rates, and availability.

Studio Loft in Downtown Cleveland!
Interior

Studio Loft in Downtown Cleveland!

2.0 star property
8.0 out of 10, Very Good, (3)
"Great location!!! Prompt communication from the manager! Would stay again! "
The price is AED 298
AED 634 total
includes taxes & fees
2 Jun - 3 Jun
Studio Loft in Downtown 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 298
AED 634 total
includes taxes & fees
1 Jun - 2 Jun
Industrial 1BD Chic close to Cavs & Browns
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 298
AED 634 total
includes taxes & fees
3 Jun - 4 Jun
1bd Modern Loft in DT Cleveland
1BD Modern Industrial Loft in DT Cleveland
Interior

1BD Modern Industrial Loft in DT Cleveland

2.0 star property
7.4 out of 10, Good, (3)
"Stay was nice. Nice quit place to just relax. Keep this place in mind for next time. "
The price is AED 298
AED 634 total
includes taxes & fees
1 Jun - 2 Jun
1BD Modern Industrial Loft in DT Cleveland
Industrial 1BD Apt in the Heart of the City
Interior

Industrial 1BD Apt in the Heart of the City

The price is AED 298
AED 636 total
includes taxes & fees
2 Jun - 3 Jun
Industrial 1BD Apt in the Heart of the City
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, (65)
"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
3 Jun - 4 Jun
Clifford House Private Home Bed & Breakfast
Industrial 2BD Apt in Downtown Cleveland!
Interior

Industrial 2BD Apt in Downtown Cleveland!

2.0 star property
8.0 out of 10, Very Good, (6)
"Weekend trip to Cleveland "
The price is AED 397
AED 902 total
includes taxes & fees
1 Jun - 2 Jun
Industrial 2BD Apt in Downtown Cleveland!
Industrial Style Living in Downtown Cleveland!
Interior

Industrial Style Living in Downtown Cleveland!

The price is AED 298
AED 801 total
includes taxes & fees
1 Jun - 2 Jun
Industrial Style Living in Downtown Cleveland!
Chic Industrial style 1BD living in Cleveland!
Interior

Chic Industrial style 1BD living in Cleveland!

2.0 star property
The price is AED 298
AED 634 total
includes taxes & fees
2 Jun - 3 Jun
Chic Industrial style 1BD living in Cleveland!
Modern Studio in Downtown CLE
Interior

Modern Studio in Downtown CLE

4.8 out of 10, (6)
"The property owners insisted on collecting my credit card information instead of charging you through VRBO. They tried to put a surprise damage deposit charge on my credit card (that wasn't mentioned in the listing) two days before check in. They didn't send the check in instructions until I called from the airport in the evening. And the apartment was filthy! I don't think the carpets had been vacuumed in weeks. I recommend you stay away from this one."
The price is AED 298
AED 704 total
includes taxes & fees
2 Jun - 3 Jun
Modern Studio in Downtown CLE
Modern 1BD in the Heart of the City!
Interior

Modern 1BD in the Heart of the City!

The price is AED 298
AED 634 total
includes taxes & fees
1 Jun - 2 Jun
Modern 1BD in the Heart of the City!
1BD Chic Loft in DT Cleveland!
Interior

1BD Chic Loft in DT Cleveland!

2.0 star property
The price is AED 298
AED 634 total
includes taxes & fees
1 Jun - 2 Jun
1BD Chic Loft in DT Cleveland!
The Lost Pearl
Exterior

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 price is AED 790
AED 829 total
includes taxes & fees
28 Jun - 29 Jun
The Lost Pearl
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 298
AED 634 total
includes taxes & fees
3 Jun - 4 Jun
Trendy Modern 1BD Industrial Loft in DT Cleveland
Industrial Townhome Style Loft in DT CLE!
View from property

Industrial Townhome Style Loft in DT CLE!

The price is AED 298
AED 801 total
includes taxes & fees
1 Jun - 2 Jun
Industrial Townhome Style Loft in DT CLE!
2BD Industrial Style Loft in Downtown Cleveland!
Interior

2BD Industrial Style Loft in Downtown Cleveland!

3.6 out of 10, (4)
"There were many deficiencies including living room seating for 2 or three only, broken appliances lack of towels and toiletries no tourist brochures, some food left in one of the cupboards code to the door did not work upon arrival, With all this said we did have regular contact with the management it just took to long for some of the items to be looked after. After many emails they did refund 1 of the 2 days we were there. The location is great for walking to downtown through the day time...
The price is AED 397
AED 1,004 total
includes taxes & fees
1 Jun - 2 Jun
2BD Industrial Style Loft in Downtown 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
The Caboose
Property grounds

The Caboose

9.4 out of 10, Exceptional, (3)
"Very unique property set in beautiful scenery. Very friendly hosts. Tiny space but perfect for 2 adults. Would definitely return. "
The Caboose
Industrial 1BD in DT Cleveland
Exterior

Industrial 1BD in DT Cleveland

2.0 star property
Industrial 1BD in DT Cleveland
Cozy 1BD Apt in DT Cleveland
Interior

Cozy 1BD Apt in DT Cleveland

2.0 star property
The price is AED 298
AED 634 total
includes taxes & fees
18 Jun - 19 Jun
Cozy 1BD 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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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.Industrial 1BD Chic close to Cavs & Browns: 17.6 mi (28.4 km) from the downtown core. 1BD Modern Industrial Loft in DT Cleveland: Situated 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 heart of downtown.
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.