Photo by Kristin DePlatchett

Search Chesterland hotels

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov

Filter by

Guest rating
Guest rating
Star rating

Top hotels and accommodation in Chesterland

Free daily buffet breakfast
Holiday Inn Express & Suites Madison by IHG
Holiday Inn Express & Suites Madison by IHG
2.5 star property
9.4 out of 10, Exceptional, (654)
"Great room and location"
United States
Francisco
The price is AU$145
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Express & Suites Madison by IHG
Room, 2 Queen Beds, Non Smoking (Pet Friendly)
Econo Lodge Cleveland Southeast - Kent
Econo Lodge Cleveland Southeast - Kent
2.0 star property
7.6 out of 10, Good, (1002)
"Good place to stay. "
United States
Michelle
The price is AU$82
includes taxes & fees
2 Nov - 3 Nov
Econo Lodge Cleveland Southeast - Kent
Lobby
La Quinta Inn & Suites by Wyndham Cleveland Macedonia
La Quinta Inn & Suites by Wyndham Cleveland Macedonia
3.0 star property
7.6 out of 10, Good, (1028)
"Great property. Good value for around $100 per night"
United States
EDWARD
The price is AU$139
includes taxes & fees
2 Nov - 3 Nov
La Quinta Inn & Suites by Wyndham Cleveland Macedonia
Pool
Comfort Inn
Comfort Inn
2.5 star property
8.4 out of 10, Very good, (1009)
"Great Place to stay in Painesville. "
United States
Robert
The price is AU$179
includes taxes & fees
23 Nov - 24 Nov
Comfort Inn
Exterior
Super 8 by Wyndham Mentor/Cleveland Area
Super 8 by Wyndham Mentor/Cleveland Area
2.0 star property
7.2 out of 10, Good, (950)
"Friendly and very clean"
United States
Patti
The price is AU$111
includes taxes & fees
2 Nov - 3 Nov
Super 8 by Wyndham Mentor/Cleveland Area
Property entrance
Motel 6 Streetsboro, OH
Motel 6 Streetsboro, OH
2.0 star property
7.4 out of 10, Good, (1004)
"great location. wonderful staff. "
United States
gaspar
The price is AU$82
includes taxes & fees
9 Nov - 10 Nov
Motel 6 Streetsboro, OH
Property grounds
Super 8 by Wyndham Twinsburg/Cleveland Area
Super 8 by Wyndham Twinsburg/Cleveland Area
2.0 star property
7.0 out of 10, Good, (862)
"Friendly staff, clean room. "
United States
Tim
The price is AU$103
includes taxes & fees
27 Oct - 28 Oct
Super 8 by Wyndham Twinsburg/Cleveland Area
Lobby
Best Western Plus Mentor-Cleveland Northeast
Best Western Plus Mentor-Cleveland Northeast
2.5 star property
9.2 out of 10, Wonderful, (1023)
"Good place to stay "
United States
Randall
The price is AU$179
includes taxes & fees
4 Nov - 5 Nov
Best Western Plus Mentor-Cleveland Northeast
Free daily buffet breakfast
Holiday Inn Express & Suites Painesville - Concord by IHG
Holiday Inn Express & Suites Painesville - Concord by IHG
2.5 star property
9.4 out of 10, Exceptional, (861)
"Number one place to stay in Lake county"
United States
Heidi
The price is AU$237
includes taxes & fees
9 Nov - 10 Nov
Holiday Inn Express & Suites Painesville - Concord by IHG
Free daily buffet breakfast
Country Inn & Suites by Radisson, Macedonia, OH
Country Inn & Suites by Radisson, Macedonia, OH
3.0 star property
7.4 out of 10, Good, (1023)
"Nice stay, clean rooms. "
United States
Rachel
The price is AU$129
includes taxes & fees
24 Nov - 25 Nov
Country Inn & Suites by Radisson, Macedonia, OH
Desk, iron/ironing board, cots/infant beds, free WiFi
Quality Inn
Quality Inn
2.5 star property
7.2 out of 10, Good, (760)
"Great price and great room"
United States
Tara
The price is AU$100
includes taxes & fees
2 Nov - 3 Nov
Quality Inn
Deluxe Room, 2 Queen Beds, Non Smoking
Fairbridge Hotel Cleveland East
Fairbridge Hotel Cleveland East
3.0 star property
6.2 out of 10, (1003)
"Everything was Great I enjoy myself I’ll be back soon thanks again."
United States
Kenneth
The price is AU$109
includes taxes & fees
27 Oct - 28 Oct
Fairbridge Hotel Cleveland East
Daily buffet breakfast (USD 7.49 per person)
Holiday Inn Cleveland Northeast - Mentor by IHG
Holiday Inn Cleveland Northeast - Mentor by IHG
3.0 star property
8.4 out of 10, Very good, (795)
"Was a great place to stay"
United States
david f
The price is AU$195
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Cleveland Northeast - Mentor by IHG
Lobby
Comfort Suites Twinsburg
Comfort Suites Twinsburg
2.5 star property
7.6 out of 10, Good, (803)
"Great location, great staff, great price."
United States
Samuel
The price is AU$159
includes taxes & fees
23 Nov - 24 Nov
Comfort Suites Twinsburg
Front of property
Steele Mansion
Steele Mansion
3.5 star property
10.0 out of 10, Exceptional, (440)
"Family had a wonderful stay while here."
United States
James
The price is AU$340
includes taxes & fees
28 Oct - 29 Oct
Steele Mansion
Lobby
Comfort Inn & Suites Streetsboro - Kent
Comfort Inn & Suites Streetsboro - Kent
2.5 star property
8.0 out of 10, Very good, (636)
"Good stay, the front desk associates were very friendly and helpful, there was a good variety on the breakfast buffet:)"
United States
Diana
The price is AU$205
includes taxes & fees
2 Nov - 3 Nov
Comfort Inn & Suites Streetsboro - Kent
Indoor pool, open 6:00 AM to 9:00 PM, pool loungers
The Aurora Inn
The Aurora Inn
3.0 star property
9.0 out of 10, Wonderful, (562)
"love staying here. food is good, rooms are nice, and the sauna is perfect "
United States
Brandon
The price is AU$195
includes taxes & fees
6 Nov - 7 Nov
The Aurora Inn
Reception
Hilton Garden Inn Cleveland East/Mayfield Village
Hilton Garden Inn Cleveland East/Mayfield Village
3.0 star property
8.4 out of 10, Very good, (978)
"Great hotel"
United States
Jude
The price is AU$151
includes taxes & fees
2 Nov - 3 Nov
Hilton Garden Inn Cleveland East/Mayfield Village
Exterior
Fairfield Inn & Suites by Marriott Cleveland Streetsboro
Fairfield Inn & Suites by Marriott Cleveland Streetsboro
2.5 star property
8.8 out of 10, Excellent, (700)
"Great place "
United States
Eric
The price is AU$197
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Cleveland Streetsboro
Property amenity
Towneplace Suites By Marriott Streetsboro
Towneplace Suites By Marriott Streetsboro
3.0 star property
8.8 out of 10, Excellent, (328)
"Clean cozy and convenient "
United States
john
The price is AU$196
includes taxes & fees
18 Nov - 19 Nov
Towneplace Suites By Marriott Streetsboro
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.
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

Enjoy a round of golf in Chesterland at Fowler's Mill Golf Course. While in this quaint area, you can savour the top-notch restaurants.
See properties

Chesterland City Park

Explore the great outdoors at Chesterland City Park, a lovely green space in Chesterland.
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
Pumpkin pickin'!
Photo by Kristin DePlatchett
Open Photo by Kristin DePlatchett

Top Chesterland Hotel Reviews

Crowne Plaza Cleveland at Playhouse Square by IHG

Crowne Plaza Cleveland at Playhouse Square by IHG

10/10 Excellent
"The stay was great. I would come back again"
David 2-night trip
Posted 1 day ago
Crowne Plaza Cleveland at Playhouse Square by IHG

More cheap accommodation in Chesterland

Econo Lodge Cleveland Southeast - Kent

Econo Lodge Cleveland Southeast - Kent

9789 State Route 14, Streetsboro, OH
The price is AU$82 per night from 2 Nov to 3 Nov
AU$82
2 Nov - 3 Nov
includes taxes & fees
7.4/10 Good! (1,001 reviews)

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 traveller data. Other good options for your stay in the area are Ramada by Wyndham Cleveland Independence and Kimpton Schofield Hotel by IHG. See all available top hotels, or vacation rentals in Chesterland.
What are some of the best holiday rentals that Chesterland has to offer?
Crown royal presidential suite and fitness center: This holiday home rental outside of Chesterland has air conditioning and WiFi 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 is staying in Chesterland like?
Visitors can enjoy all that Chesterland has to offer, including the golf courses and ski areas. There are 1495 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 Alpine Valley and Chester Town Hall. 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.

Explore a world of travel with Expedia