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Compare 40 B&B in Chesterland with updated reviews, rates, and availability.

Industrial Style Loft in DT Cleveland!
8.0 out of 10, Very Good, (1)
The price is SAR 282
SAR 789 total
includes taxes & fees
6 Nov - 7 Nov
Industrial Style Loft in DT Cleveland!
Modern Studio in Downtown CLE
5.0 out of 10, (4)
"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 SAR 207
SAR 605 total
includes taxes & fees
1 Dec - 2 Dec
Modern Studio in Downtown CLE
2BD Industrial Style Loft in Downtown Cleveland!
4.0 out of 10, (3)
"It is a really nice oft and very spacious. Beds were comfortable. Glad to have gated parking. There was some confusion with the company who handles the payment process in that they called to cancel the day of, then called to say never mind you’re okay. I did have good response from the owner via Vrbo, but received check in information very last minute that made me nervous. Check in was a breeze. Regarding the place, it was very minimal in furniture as it shows in the picture. Four adults could...
The price is SAR 338
SAR 932 total
includes taxes & fees
10 Nov - 11 Nov
2BD Industrial Style Loft in Downtown Cleveland!
Clifford House Private Home Bed & Breakfast
3.0 star property
9.4 out of 10, Exceptional, (65)
"We had a great time staying here. Neither one of us had been to Cleveland before and it was a perfect location close to great restaurants and activities. The house is beautiful and the area around it is as well. James was a great host and fun to talk to during our amazing breakfasts. We definitely will be back."
Clifford House Private Home Bed & Breakfast
The Lost Pearl
3.5 star property
9.8 out of 10, Exceptional, (43)
"I dint like the room so small i think there should be hand rails at the 2 steps to get in front door."
The price is SAR 808
SAR 848 total
includes taxes & fees
1 Dec - 2 Dec
The Lost Pearl
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 price is SAR 657
SAR 1,130 total
includes taxes & fees
6 Nov - 7 Nov
The Caboose
Homestead House B&B
4.0 star property
10.0 out of 10, Exceptional, (58)
"Dee was great! She's a top-notch, Paris-trained chef and she made the most wonderful breakfasts for us. And on the day we left, we had to leave before breakfast was normally served, so she made us a "to-go" breakfast before we left that was delicious! Thanks so much, Dee, for your wonderful hospitality!!!"
Homestead House B&B
Modern Industrial Style in DT Cleveland!
2.0 out of 10, (1)
"The booking process was a mess. Its not explained at all on the booking. The apartment was not clean! There was green stuff all over the bed. Stained bedding and pillows! Burn holes in the carpet! Burn hole in the toilet seat. There was a glob of hair in the silverware drawer! Contacted the property manager and their solution was to contact the housekeeping team. My solution was not to stay and request a refund. They immediately directed me to VRBO and stopped communicating. DONT DEAL WITH THEM!"
Modern Industrial Style in DT Cleveland!
Studio Loft in Downtown Cleveland!
2.0 star property
The price is SAR 207
SAR 526 total
includes taxes & fees
10 Nov - 11 Nov
Studio Loft in Downtown Cleveland!
Industrial Townhome Style Loft in DT CLE!
The price is SAR 282
SAR 789 total
includes taxes & fees
6 Nov - 7 Nov
Industrial Townhome Style Loft in DT CLE!
Chic Industrial style 1BD living in Cleveland!
2.0 star property
The price is SAR 244
SAR 563 total
includes taxes & fees
9 Nov - 10 Nov
Chic Industrial style 1BD living in Cleveland!
Industrial Style 1BD loft in DT Cleveland!
The price is SAR 244
SAR 649 total
includes taxes & fees
6 Nov - 7 Nov
Industrial Style 1BD loft in DT Cleveland!
Modern 1BD in the Heart of the City!
2.0 star property
10.0 out of 10, Exceptional, (1)
"Updated Modern Warehouse Feel. Nice Accommodations. Secure Gated Parking"
The price is SAR 244
SAR 563 total
includes taxes & fees
6 Nov - 7 Nov
Modern 1BD in the Heart of the City!
1BD Chic Loft in DT Cleveland!
2.0 star property
The price is SAR 244
SAR 563 total
includes taxes & fees
6 Nov - 7 Nov
1BD Chic Loft in DT Cleveland!
Industrial Chic 1BD loft in Downtown Cleveland!
The price is SAR 244
SAR 649 total
includes taxes & fees
6 Nov - 7 Nov
Industrial Chic 1BD loft in Downtown Cleveland!
Stylish 1BD in Downtown Cleveland
10.0 out of 10, Exceptional, (1)
The price is SAR 244
SAR 649 total
includes taxes & fees
6 Nov - 7 Nov
Stylish 1BD in Downtown Cleveland
Industrial 1BD loft in Downtown CLE!
8.0 out of 10, Very Good, (1)
"We were happy with the accommodations. They matched what we saw in the listing. The hosts were responsive on getting back to us when we had questions. The location was very convenient to downtown, and the Rock and Roll Hall of Fame. The neighborhood looks to be in the process of gentrifying, but was generally safe. "
The price is SAR 244
SAR 649 total
includes taxes & fees
6 Nov - 7 Nov
Industrial 1BD loft in Downtown CLE!
Industrial Style Living in Downtown Cleveland!
The price is SAR 282
SAR 789 total
includes taxes & fees
6 Nov - 7 Nov
Industrial Style Living in Downtown Cleveland!
Modern & Cozy Apt in DT Cleveland
2.0 star property
Modern & Cozy Apt in DT Cleveland
Industrial Style Living in Downtown CLE!
2.0 star property
Industrial Style Living in Downtown CLE!
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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Other property types in Chesterland

The Abbey Apartments By Barsala
4.0 star property
8.4 out of 10, Very Good, (65)
"I would highly recommend. The building was incredible. Almost brand new, beautiful and clean. The check in and out process was easy and flawless and the location was convenient to everything you would with to do in downtown. I will definitely be staying here again when I am back in Cleveland. "
The Abbey Apartments By Barsala
CLE BNB Getaway ★ 15 Guests ★ Stunning Kitchen ★ Game Room ★ Big Fenced Yard
8.8 out of 10, Excellent, (67)
"It went well and was beyond what we expected."
The price is SAR 323
SAR 1,108 total
includes taxes & fees
11 Nov - 12 Nov
CLE BNB Getaway ★ 15 Guests ★ Stunning Kitchen ★ Game Room ★ Big Fenced Yard
Relaxing Downtown Apartment
7.8 out of 10, Good, (14)
"This unit suited our needs for an enjoyable weekend stay in Cleveland to check out a couple baseball games and RRHOF. Host was responsive and timely in responses. Location is in the University area about a 15-20 min walk from downtown core. Unit was clean and as described in the ad. Safe above ground parking provided that has in-out access. Re: the odor noted by others: there is a deodorizer continuously circulated into the hallways of the building but I didn’t find it overly noticeable or...
The price is SAR 300
SAR 739 total
includes taxes & fees
7 Nov - 8 Nov
Relaxing Downtown Apartment
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.

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 interested in playing some golf on your trip, Fowler’s Mill Golf Course is a good spot to tee off.
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.
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?
If you’re looking for some activities to entertain you on your trip, consider visiting Fowler’s Mill Golf Course and Alpine Valley. You might check out Chagrin River if you have time 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.