Photo by Kristin DePlatchett

Chesterland Hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Chesterland hotels

Holiday Inn Express & Suites Madison by IHG

2.5 star property
9.4 out of 10, Exceptional, (582)
"Great place to stay."
The price is P4,926
P5,677 total
includes taxes & fees
Aug 3 - Aug 4
Holiday Inn Express & Suites Madison by IHG

Econo Lodge Cleveland Southeast - Kent

2.0 star property
7.4 out of 10, Good, (972)
"Easy check in, clean, comfortable beds"
The price is P2,824
P3,191 total
includes taxes & fees
Jul 15 - Jul 16
Econo Lodge Cleveland Southeast - Kent

La Quinta Inn & Suites by Wyndham Cleveland Macedonia

3.0 star property
7.6 out of 10, Good, (1013)
"Love to stay at this hotel, very clean and very pleasant staff. Highly recommend !"
The price is P5,219
P6,015 total
includes taxes & fees
Aug 4 - Aug 5
La Quinta Inn & Suites by Wyndham Cleveland Macedonia

Comfort Inn

2.5 star property
8.4 out of 10, Very Good, (931)
"Very clean and friendly staff "
The price is P5,533
P6,377 total
includes taxes & fees
Jul 27 - Jul 28
Comfort Inn

Super 8 by Wyndham Mentor/Cleveland Area

2.0 star property
7.2 out of 10, Good, (903)
"nice place"
The price is P3,938
P4,539 total
includes taxes & fees
Jul 16 - Jul 17
Super 8 by Wyndham Mentor/Cleveland Area

Steele Mansion

3.5 star property
10.0 out of 10, Exceptional, (416)
"Beautifully renovated property with comfortable rooms in a quaint small town. "
The price is P10,515
P11,803 total
includes taxes & fees
Jul 16 - Jul 17
Steele Mansion

Residence Inn By Marriott Cleveland Mentor

3.0 star property
9.0 out of 10, Wonderful, (355)
"Good location nice room pool"
The price is P7,739
P8,919 total
includes taxes & fees
Jul 31 - Aug 1
Residence Inn By Marriott Cleveland Mentor

Best Western Plus Mentor-Cleveland Northeast

2.5 star property
9.2 out of 10, Wonderful, (1006)
"Good breakfast."
The price is P6,194
P7,138 total
includes taxes & fees
Aug 3 - Aug 4
Best Western Plus Mentor-Cleveland Northeast

Motel 6 Streetsboro, OH

2.0 star property
7.4 out of 10, Good, (1002)
"This was by far the best motel ive ever been to"
The price is P2,711
P3,064 total
includes taxes & fees
Jul 15 - Jul 16
Motel 6 Streetsboro, OH

Holiday Inn Express And Suites Painesville - Concord by IHG

2.5 star property
9.4 out of 10, Exceptional, (808)
"Clean,comfortable and loved the location. "
The price is P6,055
P6,979 total
includes taxes & fees
Jul 20 - Jul 21
Holiday Inn Express And Suites Painesville - Concord by IHG

Super 8 by Wyndham Twinsburg/Cleveland Area

2.0 star property
7.0 out of 10, Good, (813)
"Easy check in room was clean, clerk was nice, price was great!"
The price is P3,107
P3,581 total
includes taxes & fees
Jul 20 - Jul 21
Super 8 by Wyndham Twinsburg/Cleveland Area

Country Inn & Suites by Radisson, Macedonia, OH

3.0 star property
7.6 out of 10, Good, (1016)
"Comfortable beds, clean facilities, coffee available upon arrival. Quiet & convenient to interstate. "
The price is P4,813
P5,547 total
includes taxes & fees
Aug 13 - Aug 14
Country Inn & Suites by Radisson, Macedonia, OH

Holiday Inn Cleveland Northeast - Mentor by IHG

3.0 star property
8.4 out of 10, Very Good, (747)
"Onsite restaurant and bar "
The price is P6,055
P6,979 total
includes taxes & fees
Jul 20 - Jul 21
Holiday Inn Cleveland Northeast - Mentor by IHG

Fairbridge Hotel Cleveland East

3.0 star property
6.2 out of 10, (1008)
"The room was clean and the staff was friendly "
The price is P3,660
P4,218 total
includes taxes & fees
Jul 28 - Jul 29
Fairbridge Hotel Cleveland East

Quality Inn

2.5 star property
7.2 out of 10, Good, (694)
"The space met our family's needs and we enjoyed the breakfast!"
The price is P3,330
P3,763 total
includes taxes & fees
Jul 27 - Jul 28
Quality Inn

Comfort Suites Twinsburg

2.5 star property
7.8 out of 10, Good, (745)
"Staff was great"
The price is P5,195
P6,326 total
includes taxes & fees
Aug 4 - Aug 5
Comfort Suites Twinsburg

Mentor Home Inn

2.0 star property
5.8 out of 10, (624)
"The renovations are coming along nicely, and it's convenient for getting off from I-90."
The price is P4,016
P4,629 total
includes taxes & fees
Jul 15 - Jul 16
Mentor Home Inn

Hampton Inn Madison

2.5 star property
9.6 out of 10, Exceptional, (703)
"We felt so welcomed here. The staff was kind and attentive. The complimentary breakfast was great! We would definitely stay here again and recommend to friends and family."
The price is P5,954
P6,862 total
includes taxes & fees
Jul 27 - Jul 28
Hampton Inn Madison

The Aurora Inn

3.0 star property
9.0 out of 10, Wonderful, (481)
"Thank you Dayton for making our stay pleasant and memorable. "
The price is P6,761
P7,640 total
includes taxes & fees
Jul 28 - Jul 29
The Aurora Inn

Extended Stay America Select Suites - Cleveland - Mentor

2.5 star property
6.2 out of 10, (590)
"The property was very clean and safe. We greatly enjoyed our visit to Mentor, OH."
The price is P3,406
P3,925 total
includes taxes & fees
Jul 15 - Jul 16
Extended Stay America Select Suites - Cleveland - Mentor
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

The Westin Cleveland Downtown, located 18.3 mi (29.5 km) from the heart of Chesterland, is a top choice for your stay based on our traveler data. Two other choices for your visit to the area are Crowne Plaza Cleveland at Playhouse Square by IHG and Hotel Indigo Cleveland Downtown 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 room reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you have a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chesterland.

Where can I learn more about changing or cancelling my trip to Chesterland?

For more details about picking new dates or cancelling your trip to Chesterland, go to https://www.expedia.com/service/.

What's the best place to stay near Alpine Valley?

Punderson Manor Lodge and Conference Center is one of the top choices for your stay based on our traveler data, and this 3.5-star hotel offers a marina and a golf course. You'll find it 5.4 mi (8.7 km) from Alpine Valley. Other good options in the area include Red Maple Inn and Holiday Inn Express And Suites Painesville - Concord, an IHG Hotel.

What about the best place to stay close to Fowler's Mill Golf Course?

One of the top choices for your stay is Punderson Manor Lodge and Conference Center, located 4.9 mi (7.9 km) from Fowler's Mill Golf Course, and this 3.5-star hotel offers a marina and a golf course. Red Maple Inn and Staybridge Suites Cleveland Mayfield Heights Beachwood, an IHG Hotel are two other good choices within the area.

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 onsite pool.

What is the best hotel near Hopkins International Airport (CLE)?

Sheraton Cleveland Airport Hotel is a popular 3.5-star hotel featuring a restaurant and an indoor pool. It's located a short 0.3 mi (0.4 km) from Hopkins Intl. Airport. Other accommodations close to the airport are Hilton Garden Inn Cleveland Airport and Howard Johnson by Wyndham Cleveland Airport.

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 1353 hotels and other accommodations in the surrounding area. Find out more about Chesterland.

What is there to see in Chesterland?

Favorite places to visit include Fowler's Mill Golf Course, Alpine Valley, and Chagrin River. Additionally, you'll find Progressive Field in the area. Check out what more 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 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.