𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chesterland (2026)

Our top choices for Chesterland hotels

Individually furnished, desk, free WiFi, bed sheets

Motel 6 Streetsboro, OH

Streetsboro

Rupert

includes taxes & fees

2 Jun - 3 Jun

Pillow-top beds, blackout curtains, WiFi, bed sheets

Willow Lodge Willoughby – Cleveland Mentor

Willoughby

Kynyon

includes taxes & fees

31 May - 1 Jun

Desk, blackout curtains, iron/ironing board, free cots/infant beds

Super 8 by Wyndham Mentor/Cleveland Area

Mentor

Brian

includes taxes & fees

14 Jun - 15 Jun

Holiday Inn Express & Suites Madison by IHG

Madison

Jacquelyn

includes taxes & fees

1 Jun - 2 Jun

Red Roof Inn Cleveland - Mentor/ Willoughby

Willoughby

Richard

includes taxes & fees

23 Jun - 24 Jun

Desk, blackout curtains, iron/ironing board, free WiFi

SkyLight Inn Cleveland - Willoughby

Willoughby

Joyce

includes taxes & fees

31 May - 1 Jun

The Aurora Inn

Aurora

Jonathan

includes taxes & fees

31 May - 1 Jun

Country Inn & Suites by Radisson, Macedonia, OH

Macedonia

Francine

includes taxes & fees

31 May - 1 Jun

Comfort Inn Painesville - Concord

Painesville

Cynthia

includes taxes & fees

21 Jun - 22 Jun

Best Western Plus Mentor-Cleveland Northeast

Mentor

Keith

includes taxes & fees

11 Jun - 12 Jun

Drury Inn & Suites Cleveland Beachwood

Orange

Tiffany

includes taxes & fees

31 May - 1 Jun

Desk, iron/ironing board, cots/infant beds, free WiFi

Quality Inn Streetsboro - Kent

Streetsboro

Nathan

includes taxes & fees

31 May - 1 Jun

Fairfield Inn & Suites by Marriott Cleveland Streetsboro

Streetsboro

Stephen

includes taxes & fees

14 Jun - 15 Jun

Holiday Inn Express & Suites Painesville - Concord by IHG

Painesville

David

includes taxes & fees

21 Jun - 22 Jun

Hampton Inn & Suites Cleveland Southeast/Streetsboro

Streetsboro

Michael

includes taxes & fees

21 Jun - 22 Jun

Desk, soundproofing, free cots/infant beds, free WiFi

Super 8 by Wyndham Twinsburg/Cleveland Area

Twinsburg

Alicia

includes taxes & fees

28 Jun - 29 Jun

Hampton Inn Madison

Madison

Joseph

includes taxes & fees

28 Jun - 29 Jun

La Quinta Inn & Suites by Wyndham Cleveland Macedonia

Macedonia

April

includes taxes & fees

31 May - 1 Jun

Red Carpet Inn

Garfield Heights

Ryan

includes taxes & fees

31 May - 1 Jun

TownePlace Suites by Marriott Cleveland Solon

Solon

vedat

includes taxes & fees

7 Jun - 8 Jun

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Stay near popular Chesterland attractions

Fowler's Mill Golf Course

4.0/5 (1 review)

This Pete Dye masterpiece challenges golfers with three distinct nine-hole courses woven through natural landscapes. Test your strategy on the Lake nine's signature Coastline hole where precision trumps power.

See properties

Learn more about Chesterland

Maple syrup flows freely at Patterson Fruit Farm, where families pick seasonal produce and enjoy fresh-baked treats. Explore the Western Reserve's rural charm at Holden Arboretum in nearby Kirtland, or sample local wines along the Grand River Valley wine trail.

See all hotels in Chesterland

Chesterland, Ohio, USA - 2-21-22: A small bridge in the Bessie Benner Metzenbaum Park

Top Chesterland Hotel Reviews

Holiday Inn Cleveland Clinic by IHG

10/10 Excellent

"I always stay here when I have appointments at Cleveland Clinic. The staff are always nice. The restaurant has good food. The rooms are always clean. My number1 choice😊😊"

Hotel Indigo Cleveland Downtown by IHG

6/10 Okay

"Positives first, loved how spacious the rooms are, the breakfast is to die for. The BEST hotel breakfast I’ve had so far & friendly staff. Negatives, my first room (my original) door did not close properly unless you lifted and closed it due to the alignment. When I moved to my second room the bath tub could use a DEEP cleaning plus the paint was chipped by the drain."

Fidelity Hotel

10/10 Excellent

"From start to finish, our stay was perfect. The hotel is gorgeous inside with attention to detail, the textures and warm palette made you feel very comfortable. Our room was comfortable with high end finishings, the shower was great. Well stocked mini bar and I loved that a steamer was in the closet. Nice touch. King size bed was very comfortable with a good pillow selection. Now for The Club Room restaurant, our first night we went in for a nightcap and the east meets west old fashioned was divine! We went back the next day for happy hour and tried a variety of local brews with the herbed fries, delicious. The staff are really what make this hotel stand out though, service was impeccable and the location is situated that we didn’t need our car and just walked everywhere. We will be back!"

The Glidden House

10/10 Excellent

"We loved our stay. We drove in and parked and left the car for the two days we stayed and explored the Art Museum. The location is perfect to go see some art then go to the room for a break, and then back to the museum. We took advantage of both the coffee and tea available 24hrs, and even drink on the patio. Both nights were quiet and comfortable, we slept wonderfully. The shower was good, both of us had hot water and good pressure throughout. I would definitely stay again for an art museum get away next exhibition."

Drury Plaza Hotel Cleveland Downtown

10/10 Excellent

"Awesome all around !!!!! Clean and comfortable room. Very convenient! Breakfast every morning. with Fresh eggs AND Pancakes as well as more! Something for everyone! Also the evening with light dinners /and snacks- 5:30 pm to 7pm including wine, beer and drinks The perfect location -Could easily walk to sites-and also there are free trollies that can take u around the center. if u want But most important - the staff are amazing! Very helpful and personable ! Definitely recommend!"

Wyndham Independence

2/10 Terrible

"Stay away from this place the rooms were disgusting and not clean at all I literally slept in my street clothes after a long trip as a trucker I wanted a shower but I wasn’t going anywhere near that shower. Between the beds smelled like piss there was thousands of rat or rodent turds in the AC vent so I didn’t dare turn on the air I baked all night. I’m praying to god I can post the pics here also had freshly dried blood on my sheets"

More cheap stays in Chesterland

Econo Lodge Cleveland Southeast - Kent

9789 State Route 14 Streetsboro OH

S$82

14 Jun - 15 Jun

includes taxes & fees

7.8/10 Good! (1,003 reviews)

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 Hotel Cleveland, Autograph Collection. 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 is staying in Chesterland like?

Visitors can enjoy all that Chesterland has to offer, including the golf courses and ski areas. There are 1543 hotels and other accommodation options in the surrounding area. Find out more about Chesterland.

What is there to see in Chesterland?

The picturesque setting of Chagrin River and Chesterland City Park exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Fowler's Mill Golf Course and West Geauga Plaza. 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.

Chesterland Hotels from S$82

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chesterland

Check prices for these dates

Filter by

Our top choices for Chesterland hotels

Motel 6 Streetsboro, OH

Willow Lodge Willoughby – Cleveland Mentor

Super 8 by Wyndham Mentor/Cleveland Area

Holiday Inn Express & Suites Madison by IHG

Red Roof Inn Cleveland - Mentor/ Willoughby

SkyLight Inn Cleveland - Willoughby

The Aurora Inn

Country Inn & Suites by Radisson, Macedonia, OH

Comfort Inn Painesville - Concord

Best Western Plus Mentor-Cleveland Northeast

Drury Inn & Suites Cleveland Beachwood

Quality Inn Streetsboro - Kent

Fairfield Inn & Suites by Marriott Cleveland Streetsboro

Holiday Inn Express & Suites Painesville - Concord by IHG

Hampton Inn & Suites Cleveland Southeast/Streetsboro

Super 8 by Wyndham Twinsburg/Cleveland Area

Hampton Inn Madison

La Quinta Inn & Suites by Wyndham Cleveland Macedonia

Red Carpet Inn

TownePlace Suites by Marriott Cleveland Solon

Stay near popular Chesterland attractions

Fowler's Mill Golf Course

Learn more about Chesterland

Top Chesterland Hotel Reviews

Holiday Inn Cleveland Clinic by IHG

More cheap stays in Chesterland

Econo Lodge Cleveland Southeast - Kent

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app