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Search B&B in Chesterland

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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 HK$1,671
HK$1,755 total
includes taxes & fees
13 Nov - 14 Nov
The Lost Pearl

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 HK$1,318
HK$1,520 total
includes taxes & fees
13 Nov - 14 Nov
The Willoughby House

Urban Industrial 1BD Stay in Cleveland

2.0 star property
Downtown Cleveland
10.0 out of 10, Exceptional, (1)
The price is HK$546
HK$1,328 total
includes taxes & fees
13 Nov - 14 Nov
Urban Industrial 1BD Stay in Cleveland

Industrial Style Living in Downtown Cleveland!

Cleveland
7.4 out of 10, Good, (3)
"Loved it"
United States
Michael V.
The price is HK$546
HK$1,581 total
includes taxes & fees
17 Nov - 18 Nov
Industrial Style Living in Downtown Cleveland!

Clifford House Private Home Bed & Breakfast

3.0 star property
Ohio City
9.4 out of 10, Exceptional, (68)
"We enjoyed our stay and enjoyed the area a great deal. Jim was a fabulous host and helped make our time there enjoyable. Extremely attentive to communication. We highly recommend!"
United States
Leigh
The price is HK$1,508
HK$1,772 total
includes taxes & fees
21 Nov - 22 Nov
Clifford House Private Home Bed & Breakfast

Cleveland 1BR – Industrial Style Living

2.0 star property
Downtown Cleveland
8.4 out of 10, Very good, (5)
"The no visitors rule is insane. This place seems to be run by AI. No human contact and strict rules with pricey consequences. If you’re a loner on a tight budget, it’s ideal. But it felt like renting out a room in your stringent parent’s house, to me. "
United States
Sherkiya W.
The price is HK$546
HK$1,328 total
includes taxes & fees
13 Nov - 14 Nov
Cleveland 1BR – Industrial Style Living

Modern 2BR Gem in the City’s Heart

2.0 star property
Downtown Cleveland
7.6 out of 10, Good, (8)
"The space in this building has great potential. Pros: Ease of check in, communication with the property manager Cons: Lack of furniture to sit on, showers (water pressure), cleanliness (very dusty), overwhelming scent of “Febreze” type smell on the furniture and sheets, Threadbare linens in the bathroom including no bath mat in one of the bathrooms, We enjoyed our stay, for the most part, because we were catching up with friends. The space has a ton of potential to be clean, comfortable...
United States
Shannon M.
The price is HK$714
HK$1,727 total
includes taxes & fees
13 Nov - 14 Nov
Modern 2BR Gem in the City’s Heart

Industrial Townhome Style Loft in DT CLE!

Cleveland
The price is HK$546
HK$1,581 total
includes taxes & fees
17 Nov - 18 Nov
Industrial Townhome Style Loft in DT CLE!

Industrial 1BD Apt in the Heart of the City

Downtown Cleveland
8.0 out of 10, Very good, (1)
The price is HK$546
HK$1,332 total
includes taxes & fees
17 Nov - 18 Nov
Industrial 1BD Apt in the Heart of the City

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 HK$546
HK$1,328 total
includes taxes & fees
13 Nov - 14 Nov
Industrial-Chic 1BR in Central 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 HK$546
HK$1,328 total
includes taxes & fees
13 Nov - 14 Nov
Stylish Industrial 1BD Apartment – Cleveland

1bd Modern Loft in DT Cleveland

Downtown Cleveland
5.2 out of 10, (5)
"The bed is a flat sheet poorly tucked over the mattress, and an old, stained, flat comforter. Two flat pillows with shams that match the comforter in condition. The cleaning crew isn’t well monitored. The floor is sticky everywhere. When you grab a stool to move it, it’s sticky. The place is cute! I knew what I was getting with the area and the location, but the bed and the filthy apartment ruined it. "
United States
Jennifer L.
The price is HK$546
HK$1,328 total
includes taxes & fees
17 Nov - 18 Nov
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

Find out more about Chesterland

Chesterland B&B information

Number of reviews
150
Accommodation
27 B&B
Lowest Price
HK$1,328
Highest Price
HK$1,772

Frequently asked questions

Searching for B&Bs in Chesterland?
Whether you're on a romantic holiday and want to stay somewhere quiet, or you're a solo traveller hoping to make some connections, B&Bs can be a great choice for many travellers. If you're looking to play some golf while in Chesterland, you can perfect your swing at Berkshire Hill Golf Course and Fowler's Mill Golf Course.
Are you interested in an apartment instead of a traditional hotel?
Every B&B has a unique charm — whether it's a comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the tiny details are what make bed and breakfasts the perfect escape.
What are the top B&Bs in Chesterland?
Take a look at this B&B in the area: The Willoughby House: 10 rooms. 8.6 mi (13.9 km) from the heart of Chesterland. Enjoy the on-site dining and bar/lounge.
When is the best time to book my B&B in Chesterland?
When you're planning your stay in Chesterland, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Chesterland are January, November, December and March, with each month seeing an average of 17 cm 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 should put Alpine Valley and Chester Town Hall on your list if you want to see more of the area.
How can I get to and around Chesterland?
You can plan your excursions 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 heart of the city. 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 to rent a car for your trip.