A wooden bridge over a snow-covered path in a forest.

Chesterland Hotels from S$100

  • 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

This weekend
17 Jul - 19 Jul
Next weekend
24 Jul - 26 Jul

Filter by

Star rating

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Chesterland hotels

Breakfast included
Free daily buffet breakfast

Holiday Inn Express & Suites Madison by IHG

Holiday Inn Express & Suites Madison by IHG
2.5 star property
Madison
9.4 out of 10, Exceptional, (737 reviews)
"Clean room Very friendly Staff Delicious breakfast"
United States
Catalina
The price is S$164
includes taxes & fees
30 Jul - 31 Jul
Holiday Inn Express & Suites Madison by IHG
Private kitchen

TownePlace Suites by Marriott Painesville Mentor

TownePlace Suites by Marriott Painesville Mentor
3.0 star property
Mentor
9.8 out of 10, Exceptional, (6 reviews)
"This property just recently opened and it was so nice!! The rooms are so clean and stocked with things I wouldnā€™t have expected. On top of the that the staff was so friendly. I will definitely be back. "
United States
Natacia
The price is S$228
includes taxes & fees
19 Jul - 20 Jul
TownePlace Suites by Marriott Painesville Mentor
Breakfast, lunch and dinner served

Best Western Plus Mentor-Cleveland Northeast

Best Western Plus Mentor-Cleveland Northeast
2.5 star property
Mentor
9.2 out of 10, Wonderful, (1,018 reviews)
"Front desk was very courteous. Room and entire hotel was clean. Breakfast was wonderful with a great variety. Definitely recommend this hotel!"
United States
Denise
The price is S$166
includes taxes & fees
20 Jul - 21 Jul
Best Western Plus Mentor-Cleveland Northeast
Serves lunch, dinner and happy hour

The Aurora Inn

The Aurora Inn
3.0 star property
Aurora
9.0 out of 10, Wonderful, (723 reviews)
"Beautiful older inn, we went here for a getaway and really enjoyed our stay."
United States
KIMBERLY
The price is S$151
includes taxes & fees
26 Jul - 27 Jul
The Aurora Inn
Terrace/patio

Hampton Inn Madison

Hampton Inn Madison
2.5 star property
Madison
9.6 out of 10, Exceptional, (854 reviews)
The price is S$195
includes taxes & fees
26 Jul - 27 Jul
Hampton Inn Madison
Free daily buffet breakfast

Fairfield Inn & Suites by Marriott Cleveland Streetsboro

Fairfield Inn & Suites by Marriott Cleveland Streetsboro
3.0 star property
Streetsboro
8.8 out of 10, Excellent, (787 reviews)
"Great stay overall!"
United States
Stephen
The price is S$179
includes taxes & fees
19 Jul - 20 Jul
Fairfield Inn & Suites by Marriott Cleveland Streetsboro
Pool

Comfort Inn Painesville - Concord

Comfort Inn Painesville - Concord
2.5 star property
Painesville
8.4 out of 10, Very good, (1,001 reviews)
"This is a recently renovated Comfort Inn. The lobby is welcoming and the rooms are exceptionally clean. The beds are super comfortable!!"
United States
James
The price is S$183
includes taxes & fees
26 Jul - 27 Jul
Comfort Inn Painesville - Concord
Front of property

Steele Mansion

Steele Mansion
3.5 star property
Painesville
10.0 out of 10, Exceptional, (459 reviews)
"Lovely Inn with beautiful decor and"
United States
Rachel
The price is S$273
includes taxes & fees
21 Jul - 22 Jul
Steele Mansion
Exterior

Red Roof Inn Cleveland - Mentor/ Willoughby

Red Roof Inn Cleveland - Mentor/ Willoughby
2.0 star property
Willoughby
7.4 out of 10, Good, (1,000 reviews)
"You"
United States
Janean
The price is S$96
includes taxes & fees
19 Jul - 20 Jul
Red Roof Inn Cleveland - Mentor/ Willoughby
Front of property ā€“ evening/night

Holiday Inn Express & Suites Painesville - Concord by IHG

Holiday Inn Express & Suites Painesville - Concord by IHG
2.5 star property
Painesville
9.4 out of 10, Exceptional, (942 reviews)
"All staff that we encountered was very friendly and the hotel itself is very clean. Our room was good sized with two queen beds."
United States
David
The price is S$159
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Express & Suites Painesville - Concord by IHG
Individually furnished, desk, free WiFi, bed sheets

Motel 6 Streetsboro, OH

Motel 6 Streetsboro, OH
2.0 star property
Streetsboro
7.4 out of 10, Good, (1,012 reviews)
The price is S$68
includes taxes & fees
1 Aug - 2 Aug
Motel 6 Streetsboro, OH
Exterior

Country Inn & Suites by Radisson, Macedonia, OH

Country Inn & Suites by Radisson, Macedonia, OH
3.0 star property
Macedonia
7.4 out of 10, Good, (1,015 reviews)
"The shower water pressure was amazing and the breakfast was delicious!"
United States
Shelby
The price is S$112
includes taxes & fees
2 Aug - 3 Aug
Country Inn & Suites by Radisson, Macedonia, OH
Indoor pool

Hampton Inn & Suites Cleveland Southeast/Streetsboro

Hampton Inn & Suites Cleveland Southeast/Streetsboro
2.5 star property
Streetsboro
9.0 out of 10, Wonderful, (1,005 reviews)
" The room was very clean, quiet, the breakfast variety was excellent and the atmosphere friendly and relaxing. I will definitely stay again on my way back through. "
United States
Gretchen
The price is S$179
includes taxes & fees
26 Jul - 27 Jul
Hampton Inn & Suites Cleveland Southeast/Streetsboro
Exterior

The Westin Cleveland Downtown

The Westin Cleveland Downtown
4.0 star property
Downtown Cleveland
9.0 out of 10, Wonderful, (96 reviews)
"enjoyed our stay helpful and friendly staff"
United States
Joan
The price is S$227
includes taxes & fees
26 Jul - 27 Jul
The Westin Cleveland Downtown
Bar (on property)

Holiday Inn Cleveland Northeast - Mentor by IHG

Holiday Inn Cleveland Northeast - Mentor by IHG
3.0 star property
Mentor
8.4 out of 10, Very good, (859 reviews)
"Breakfast was great and staff are friendly."
United States
Deborah
The price is S$194
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Cleveland Northeast - Mentor by IHG
Indoor pool

Comfort Inn & Suites Streetsboro - Kent

Comfort Inn & Suites Streetsboro - Kent
2.5 star property
Streetsboro
8.0 out of 10, Very good, (679 reviews)
"Pool was just right for a 5 and 9 year old. Breakfast was good. Cinnamon waffles were a hit."
United States
Margaret
The price is S$177
includes taxes & fees
26 Jul - 27 Jul
Comfort Inn & Suites Streetsboro - Kent
Outdoor pool

The Bertram Inn & Conf Ctr Trademark Collection by Wyndham

The Bertram Inn & Conf Ctr Trademark Collection by Wyndham
3.5 star property
Aurora
7.4 out of 10, Good, (205 reviews)
"Nice staff clean room good price! "
United States
Ryan
The price is S$223
includes taxes & fees
16 Jul - 17 Jul
The Bertram Inn & Conf Ctr Trademark Collection by Wyndham
Lobby

Drury Inn & Suites Cleveland Beachwood

Drury Inn & Suites Cleveland Beachwood
3.0 star property
Orange
9.4 out of 10, Exceptional, (1,024 reviews)
"Good stay will Stay again"
United States
Cari
The price is S$199
includes taxes & fees
19 Jul - 20 Jul
Drury Inn & Suites Cleveland Beachwood
Indoor pool

La Quinta Inn & Suites by Wyndham Cleveland Macedonia

La Quinta Inn & Suites by Wyndham Cleveland Macedonia
3.0 star property
Macedonia
7.6 out of 10, Good, (1,084 reviews)
"It is very close to the national park, making it a convenient place to rest with a great location. The parking lot is large, and while the breakfast is average, it is acceptable"
United States
Liyong
The price is S$141
includes taxes & fees
2 Aug - 3 Aug
La Quinta Inn & Suites by Wyndham Cleveland Macedonia
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

8.0/10 (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
A wooden bridge over a snow-covered path in a forest.

Top Chesterland Hotel Reviews

Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG

8/10 Good
"Lots of noise due to an elevator repair."
Joseph 1-night trip
Posted less than an hour ago
Hotel Indigo Cleveland Downtown by IHG

More cheap stays in Chesterland

SkyLight Inn Cleveland - Willoughby

SkyLight Inn Cleveland - Willoughby

34600 Maplegrove Rd Willoughby OH
The price is S$100 per night from 30 Jul to 31 Jul
S$100
30 Jul - 31 Jul
includes taxes & fees
6.6/10 (1,012 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 Hotel Indigo Cleveland Downtown by IHG and Hilton Garden Inn Cleveland Downtown. 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. Top sights around the area include Progressive Field and Rocket Arena. There are 1477 hotels and other accommodation options in the surrounding area. Find out more about Chesterland.
What is there to see in Chesterland?
Natural beauty is on display at Chesterland City Park, Silo Picnic Area and Chagrin River. Additionally, you'll find Progressive Field and Rocket Arena 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 20Ā°C, while the coldest months are January and February, with an average of -1Ā°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