Photo by Kristin DePlatchett

Chesterland Hotels from from S$53

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Top 10 trending Chesterland hotels

Hampton Inn Madison

2.5 star property
9.6 out of 10, Exceptional, (665)
"Loved it! Very clean, comfortable, and relaxing. Shower was great and bed was comfortable. Room was very spacious. "
The price is S$156
includes taxes & fees
16 Apr - 17 Apr
Hampton Inn Madison

Holiday Inn Express & Suites Madison by IHG

2.5 star property
9.4 out of 10, Exceptional, (523)
"Clean room, fast service, nice bed, good breakfast "
The price is S$134
includes taxes & fees
20 Apr - 21 Apr
Holiday Inn Express & Suites Madison by IHG

Holiday Inn Express And Suites Painesville - Concord by IHG

2.5 star property
9.4 out of 10, Exceptional, (773)
"My stay was great. Everything was clean and organized and breakfast was perfect. Thanks for having an egg whites option. Only tiny issues were a light bulb needed to be replaced in the corner lamp and I noticed a small section of caulk missing in the shower. "
The price is S$178
includes taxes & fees
27 Apr - 28 Apr
Holiday Inn Express And Suites Painesville - Concord by IHG

Comfort Inn

2.5 star property
8.4 out of 10, Very good, (886)
"Location to entertainment and dining "
The price is S$136
includes taxes & fees
20 Apr - 21 Apr
Comfort Inn

Steele Mansion

3.5 star property
10.0 out of 10, Exceptional, (401)
"The history of the house was very interesting. The atmosphere and the house were beautiful. "
The price is S$263
includes taxes & fees
16 Apr - 17 Apr
Steele Mansion

Motel 6 Streetsboro, OH

2.0 star property
7.4 out of 10, Good, (1074)
"Loved the easy and fast check in. Clean room. Friendly staff! "
The price is S$53
includes taxes & fees
6 Apr - 7 Apr
Motel 6 Streetsboro, OH

Quality Inn

2.5 star property
7.4 out of 10, Good, (660)
"This was an impromptu stay and was worth it. The staff was friendly and helpful. The place was clean. The hallways were clean also. The room was clean. The light switch did not work but the lamp was bright enough. There was plenty of towels. The water was nice and hot (just like I like it)! There were 2 beds in our room. The one we slept in was perfect! It was comfortable and with 4 pillows (which is a plus) because my husband gets 1 and I get the other 3! The stay was quiet but there is outside...
The price is S$83
includes taxes & fees
13 Apr - 14 Apr
Quality Inn

Comfort Inn & Suites Streetsboro - Kent

2.5 star property
8.0 out of 10, Very good, (505)
"Friendly staff "
The price is S$147
includes taxes & fees
21 Apr - 22 Apr
Comfort Inn & Suites Streetsboro - Kent

The Aurora Inn

3.0 star property
9.0 out of 10, Wonderful, (421)
"Very cute. "
The price is S$153
includes taxes & fees
20 Apr - 21 Apr
The Aurora Inn

Holiday Inn Express Hotel & Suites Cleveland-Streetsboro by IHG

2.5 star property
8.2 out of 10, Very good, (643)
"Front desk was great at checkin. Original room was an adjoining room but there was loud children next door. Went to the front desk and they moved my room. Very helpful & friendly "
The price is S$150
includes taxes & fees
6 Apr - 7 Apr
Holiday Inn Express Hotel & Suites Cleveland-Streetsboro by IHG

Extended Stay America Select Suites - Cleveland - Mentor

2.5 star property
6.2 out of 10, (560)
"It was ok .. until some kid was screaming continuously off and on for hours throughout the night "
The price is S$103
includes taxes & fees
13 Apr - 14 Apr
Extended Stay America Select Suites - Cleveland - Mentor

Hampton Inn & Suites Cleveland Mentor

2.5 star property
8.6 out of 10, Excellent, (664)
"Needed to have a meat not sausage and gravy "
The price is S$161
includes taxes & fees
27 Apr - 28 Apr
Hampton Inn & Suites Cleveland Mentor

Residence Inn By Marriott Cleveland Mentor

3.0 star property
9.0 out of 10, Wonderful, (336)
"Nice staff"
The price is S$230
includes taxes & fees
27 Apr - 28 Apr
Residence Inn By Marriott Cleveland Mentor

Hampton Inn & Suites Cleveland Southeast/Streetsboro

2.5 star property
9.0 out of 10, Wonderful, (901)
"Friendly staff. Room was clean and comfortable. Hotel is showing a little wear and tear. Bit of an odd smell (locker room?) that I would have said something about if we were staying longer than one night. "
The price is S$166
includes taxes & fees
16 Apr - 17 Apr
Hampton Inn & Suites Cleveland Southeast/Streetsboro

Econo Lodge Cleveland Southeast - Kent

2.0 star property
7.4 out of 10, Good, (871)
"Good"
The price is S$58
includes taxes & fees
6 Apr - 7 Apr
Econo Lodge Cleveland Southeast - Kent

Fairfield Inn & Suites by Marriott Cleveland Streetsboro

2.5 star property
8.8 out of 10, Excellent, (600)
"The staff. "
The price is S$142
includes taxes & fees
20 Apr - 21 Apr
Fairfield Inn & Suites by Marriott Cleveland Streetsboro

Towneplace Suites By Marriott Streetsboro

3.0 star property
8.6 out of 10, Excellent, (293)
"Great staff. "
The price is S$142
includes taxes & fees
20 Apr - 21 Apr
Towneplace Suites By Marriott Streetsboro

The Bertram Inn & Conf Ctr Trademark Collection by Wyndham

3.5 star property
7.6 out of 10, Good, (159)
"Rooms are huge and clean, Friendly staff, great location. "
The price is S$221
includes taxes & fees
10 Apr - 11 Apr
The Bertram Inn & Conf Ctr Trademark Collection by Wyndham

Best Western Plus Mentor-Cleveland Northeast

2.5 star property
9.2 out of 10, Wonderful, (1068)
"Very safe location and reasonable price"
The price is S$156
includes taxes & fees
27 Apr - 28 Apr
Best Western Plus Mentor-Cleveland Northeast
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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Learn more about Chesterland

Experience Chesterland: its golf, skiing and more!

Photo by Kristin DePlatchett
Open Photo by Kristin DePlatchett

Frequently asked questions

Where is the best place for a stay in Chesterland?

Hotel Indigo Cleveland Downtown by IHG, located 18.2 mi (29.2 km) from the heart of Chesterland, is a top choice for your stay, based on our traveller data. Other good options for your stay in the area are The Westin Cleveland Downtown and Crowne Plaza Cleveland at Playhouse Square by IHG. See all available top hotels, or vacation rentals in Chesterland.

If I need to cancel my hotel reservation in Chesterland, will I receive a refund?

Yes, the majority of hotel reservations are refundable if you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If you have a reservation that's non-refundable, it might still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Chesterland.

What are some hotels with pools in Chesterland?

Drury Plaza Hotel Cleveland Downtown: 3-star hotel, 9-minute walk from Rocket Mortgage FieldHouse. Provides a snack bar, an indoor pool and free buffet breakfast. Hilton Cleveland Downtown and Embassy Suites by Hilton Cleveland Beachwood are two additional hotels that offer an on-site pool.

What is staying in Chesterland like?

Visitors can enjoy all that Chesterland has to offer, including the golf courses and ski areas. A top sight in the area is Progressive Field. There are 1240 hotels and other accommodation options in the surrounding area. Find out more about Chesterland.

What is there to see in Chesterland?

Favourite places to visit include Alpine Valley, Chagrin River and Fowler's Mill Golf Course. Additionally, you'll find Progressive Field in the area. Take a look at what more there is to see and do in Expedia's Chesterland guide.

What's the seasonal weather like in Chesterland?

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.