Photo by Kristin DePlatchett

Chesterland Hotels

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check Chesterland hotel prices

Tomorrow night
Next weekend

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Chesterland hotels

Holiday Inn Express And Suites Painesville - Concord, an IHG Hotel

2.5 star property
9.4 out of 10, Exceptional, (739)
"Excellent service, above and beyond the call of duty. Aaron provided ketchup for an order of food we brought in to eat in the common area. And the breakfast was outstanding. We would definitely stay here again!"
The price is €104
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express And Suites Painesville - Concord, an IHG Hotel

Punderson Manor Lodge and Conference Center

3.5 star property
9.0 out of 10, Wonderful, (228)
"The Punderson Lodge does not have an elevator. You have go up one flight of stairs and then back down another half-flight to get to your room. This is major points off. "
Punderson Manor Lodge and Conference Center

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

10.0 out of 10, Exceptional, (14)
"Very clean and organized space, had everything we needed. Great response from the host. "
The price is €134
includes taxes & fees
25 Nov - 26 Nov
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Equestrian facility .Cozy apartment in nice Chardon with AC, fitness room, WiFi

The price is €139
includes taxes & fees
25 Nov - 26 Nov
Equestrian facility .Cozy apartment in nice Chardon with AC, fitness room, WiFi

Pine Lake Trout Club Cabin #8!!!

8.0 out of 10, Very good, (7)
"It was a wonderful stay and experience! The only things was little things like the floor seemed like it was in need of vacuuming and we found looked like little kids boy short on the side of the couch but overall it was a pleasant time we had thank you!!"
The price is €187
includes taxes & fees
25 Nov - 26 Nov
Pine Lake Trout Club Cabin #8!!!

Pine Lake Trout Club Cabin #4!!!

10.0 out of 10, Exceptional, (2)
"My wife and I enjoyed our stay so much that we for sure will be returning.."
The price is €207
includes taxes & fees
25 Nov - 26 Nov
Pine Lake Trout Club Cabin #4!!!

Quiet Country Get-Away

8.8 out of 10, Excellent, (29)
"House was wonderful- especially enjoyed the jacuzzi tub. Quiet, owners easy to work with - communication excellent. Had more space than we thought it might have."
The price is €153
includes taxes & fees
2 Dec - 3 Dec
Quiet Country Get-Away

Pine Lake Trout Club Cabin #1!!!

10.0 out of 10, Exceptional, (1)
"Perfect spot for a cabin in the woods, yet centrally locate to many great offerings."
The price is €192
includes taxes & fees
25 Nov - 26 Nov
Pine Lake Trout Club Cabin #1!!!

Rustic Western Getaway

8.4 out of 10, Very good, (26)
"My husband and I stayed in the area for a wedding and wanted somewhere close to the venue, since I was in the wedding. The check-in process was so easy and convenient. The space was a little smaller than anticipated, however it was perfect for the two of us and was nice and cozy. I can’t say enough great things about the customer service, I requested a late check-out the morning we were supposed to depart (realizing a little more sleep would be nice), I received approval of my request within...
The price is €139
includes taxes & fees
2 Dec - 3 Dec
Rustic Western Getaway

Cozy two bedroom house close to Middlefield, and close to Route 80 and 422

10.0 out of 10, Exceptional, (10)
"Love staying here. It’s peaceful, quiet, clean and well set up. This is my first choice if I’m in the area! "
The price is €129
includes taxes & fees
25 Nov - 26 Nov
Cozy two bedroom house close to Middlefield, and close to Route 80 and 422

Pine Lake Trout Club Cabin #7!!!

10.0 out of 10, Exceptional, (5)
"We rented this cabin overnight to give us somewhere comfortable to stay after an event in Cleveland. The cabin was comfy, cute, and it was honestly a great time, I wish we had known how much we had liked it, we would’ve booked an extra day!"
The price is €223
includes taxes & fees
25 Nov - 26 Nov
Pine Lake Trout Club Cabin #7!!!

Pine Lake Trout Club Cabin #3!!!

8.6 out of 10, Excellent, (4)
"This cabin is absolutely beautiful. Even better... It's actually a cabin. It's not a tract house with a bunch of cutesy junk on the walls. It's an honest, purpose-built cabin. Walls are made of wood, the setting is stunning (in the woods where you can hear the trout stream), and you're set away from other properties. The kitchen is well stocked. The water pressure is good in the shower. You get hotel-style toiletries (no gross old bottles of Suave!). The beds are more comfortable than you'll...
The price is €250
includes taxes & fees
25 Nov - 26 Nov
Pine Lake Trout Club Cabin #3!!!

Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.

10.0 out of 10, Exceptional, (3)
"Cozy cabin in a private setting amongst nature but not far from sites and additional amenities. Host is gracious and has thought of just about everything one could need in an off-grid setting."
The price is €338
includes taxes & fees
26 Nov - 27 Nov
Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.

Cozy Farm Apartment

9.4 out of 10, Exceptional, (48)
"Great place with all the necessary essentials for your stay. A home away from home."
The price is €153
includes taxes & fees
2 Dec - 3 Dec
Cozy Farm Apartment

Beautiful cabin situated on wooded land with nice yard clearing and small stream

10.0 out of 10, Exceptional, (7)
"Very cozy cabin. Situated in the wilderness, the scenery is beautiful and it's very clean"
The price is €160
includes taxes & fees
28 Nov - 29 Nov
Beautiful cabin situated on wooded land with nice yard clearing and small stream

Loft Unplugged w/ Outdoor Space in Amish Country!

2.0 star property
8.0 out of 10, Very good, (2)
"The property was just beautiful!! The host and hostess was just amazing, so polite and friendly. The loft was everything I expected!! I made 2 blankets while I was there .. I didn’t use the electric!! Or battery light I saved it for my daughter and grandson for the last 2 days. And now I have not watched tv since I have been home. And I quit social media. I could live there. Please go stay !! Best thing ever !! "
Loft Unplugged w/ Outdoor Space in Amish Country!

1br-1bth- Furnished Apartment in Chardon

9.6 out of 10, Exceptional, (4)
"The apartment was very nice and the hosts appointed it very well. It is a great place to stay!"
The price is €148
includes taxes & fees
25 Nov - 26 Nov
1br-1bth- Furnished Apartment in Chardon

Geauga Maple Cottage

10.0 out of 10, Exceptional, (168)
"A friend got married in Novelty and my choice of close places to stay were hotels East or Chagrin - I made the right choice. House is on a Main Street, but it is quiet, I didn’t hear a thing either night of our stay. Owners next door and friendly. There is a bar 100 yards away which I didn’t hear a peep from. I would stay again. If you want to have cable you need to bring a fire stick or other plug in device for the tv. "
Geauga Maple Cottage

Loft Unplugged w/ Outdoor Space in Amish Country!

9.2 out of 10, Wonderful, (27)
"Really enjoyed our time here. Everything was as expected. Beautiful peaceful setting with friendly horses and helpful hosts. Highly recommended."
Loft Unplugged w/ Outdoor Space in Amish Country!

Bonnie's Guesthouse @ Peridot Equine Sanctuary

9.6 out of 10, Exceptional, (70)
"We admire folks that do good works. It is amazing to experience the love and compassion that these folks provide to these beautiful misfits. The peaceful setting and stay was a humbling experience. The location was great for our visit to Presque Isle in Erie, Pa and then to Cuyoga National Park in Ohio for bike trail rides. Highly recommend a stay and a visits to both of these beautiful parks. Mark and Vicki"
The price is €169
includes taxes & fees
29 Nov - 30 Nov
Bonnie's Guesthouse @ Peridot Equine Sanctuary
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.
Don't see what you're looking for?
See all available properties in Chesterland
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Where is the best place for a stay in Chesterland?

Extended Stay America Premier Suites - Cleveland - Independence, located 18.3 mi (29.5 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 Drury Plaza Hotel Cleveland Downtown and DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside. See all available top hotels, or vacation rentals in Chesterland.

What are some of the best holiday rentals that Chesterland has to offer?

Ohio City Getaway! Sleeps 12, Games, Near Downtown: This holiday home rental outside of Chesterland has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. See all 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 1147 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 Fowler's Mill Golf Course, Chagrin River and Alpine Valley. 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.