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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sep - 7 Sep
In one month
19 Sep - 21 Sep
In two months
17 Oct - 19 Oct

B&B in Chesterland

Our top choices for Chesterland bed & breakfast

The Caboose
Property grounds

The Caboose

9.6 out of 10, Exceptional, (4)
"We enjoyed staying the weekend in The Caboose. My husband would have enjoyed a love seat inside to sit and watch tv versus lying in bed but, it is a little place to rest your head and shower and get on with adventures. I love the outdoors and having a fire in the evening. Easy drive to a plethora of wineries. In the summer do not turn the AC down no matter what. We were comfortable and had a wonderful time."
The price is SAR 591
SAR 1,056 total
includes taxes & fees
22 Aug - 23 Aug
The Caboose
The Willoughby House
Terrace/patio

The Willoughby House

3.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful property. Nice location. Excellent lounge & restaurant."
The price is SAR 804
SAR 926 total
includes taxes & fees
4 Sep - 5 Sep
The Willoughby House
Industrial 1BD Chic close to Cavs & Browns
Interior

Industrial 1BD Chic close to Cavs & Browns

2.0 star property
9.0 out of 10, Wonderful, (2)
"Great location and very welcoming. Easy to communicate with the host. Suggested a few things to the host that would have made our stay even more fantastic. Would definitely book again when in Cleveland. "
The price is SAR 263
SAR 641 total
includes taxes & fees
24 Aug - 25 Aug
Industrial 1BD Chic close to Cavs & Browns
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, (67)
"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!"
The price is SAR 724
SAR 793 total
includes taxes & fees
25 Aug - 26 Aug
Clifford House Private Home Bed & Breakfast
Industrial Townhome Style Loft in DT CLE!
View from property

Industrial Townhome Style Loft in DT CLE!

The price is SAR 263
SAR 759 total
includes taxes & fees
25 Aug - 26 Aug
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 SAR 263
SAR 641 total
includes taxes & fees
24 Aug - 25 Aug
1BD Chic Loft in DT Cleveland!
Industrial 2BD Apt in Downtown Cleveland!
Interior

Industrial 2BD Apt in Downtown Cleveland!

2.0 star property
8.4 out of 10, Very Good, (7)
"Weekend trip to Cleveland "
The price is SAR 345
SAR 834 total
includes taxes & fees
24 Aug - 25 Aug
Industrial 2BD Apt in Downtown Cleveland!
Chic Industrial style 1BD living in Cleveland!
Interior

Chic Industrial style 1BD living in Cleveland!

2.0 star property
6.0 out of 10, (1)
The price is SAR 263
SAR 641 total
includes taxes & fees
24 Aug - 25 Aug
Chic Industrial style 1BD living in Cleveland!
Cozy 1BD Apt in DT Cleveland
Interior

Cozy 1BD Apt in DT Cleveland

2.0 star property
The price is SAR 263
SAR 641 total
includes taxes & fees
14 Sep - 15 Sep
Cozy 1BD Apt in DT Cleveland
1BD Modern Industrial Loft in DT Cleveland
Interior

1BD Modern Industrial Loft in DT Cleveland

2.0 star property
6.0 out of 10, (6)
"Stay was nice. Nice quit place to just relax. Keep this place in mind for next time. "
The price is SAR 263
SAR 641 total
includes taxes & fees
15 Sep - 16 Sep
1BD Modern Industrial Loft in DT Cleveland
Industrial Style Living in Downtown Cleveland!
Interior

Industrial Style Living in Downtown Cleveland!

6.0 out of 10, (2)
"This was a nice stay. It was rushed to get there due to outside circumstances but the unit was nice and I have no complaints. I love the windows in the living room and the fake plants were a lovely touch. I was worried about the parking situation going into it but it felt very safe and not too far of a walk. "
The price is SAR 263
SAR 759 total
includes taxes & fees
16 Sep - 17 Sep
Industrial Style Living in Downtown Cleveland!
Industrial 1BD in DT Cleveland
Interior

Industrial 1BD in DT Cleveland

2.0 star property
The price is SAR 263
SAR 641 total
includes taxes & fees
25 Aug - 26 Aug
Industrial 1BD in DT 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 SAR 263
SAR 641 total
includes taxes & fees
3 Sep - 4 Sep
Trendy Modern 1BD Industrial Loft in DT Cleveland
Industrial 1BD Apt in the Heart of the City
Interior

Industrial 1BD Apt in the Heart of the City

8.0 out of 10, Very Good, (1)
The price is SAR 263
SAR 643 total
includes taxes & fees
24 Aug - 25 Aug
Industrial 1BD Apt in the Heart of the City
1bd industrial apt in DT Cleveland
Interior

1bd industrial apt in DT Cleveland

The price is SAR 263
SAR 641 total
includes taxes & fees
24 Aug - 25 Aug
1bd industrial apt in DT Cleveland
1bd Modern Loft in DT Cleveland
Interior

1bd Modern Loft in DT Cleveland

5.0 out of 10, (4)
"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 SAR 263
SAR 641 total
includes taxes & fees
24 Aug - 25 Aug
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

Drury Plaza Hotel Cleveland Downtown

Drury Plaza Hotel Cleveland Downtown

10/10 Excellent
"Amazing hotel, great location, super comfortable room. Will definitely stay here again the next time we’re in town"
Ian 1-night trip
Posted 11 hours ago
Drury Plaza Hotel Cleveland Downtown

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 Berkshire Hill Golf Course and Fowler's Mill 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 is a B&B in the area: The Willoughby House: 10 rooms. 8.6 mi (13.9 km) from the heart of Chesterland. 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 West Geauga Plaza and West Geauga Public Library 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.