Photo by Kristin DePlatchett
Hotels in Chesterland
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Crowne Plaza Cleveland at Playhouse Square by IHG
Crowne Plaza Cleveland at Playhouse Square by IHG
3.5 star property
Downtown Cleveland
9.0 out of 10, Wonderful, (1300)
9.0/10
Wonderful
(1300)
The price is $93
$93
$109 total
includes taxes & fees
Dec 23 - Dec 24
The Westin Cleveland Downtown
The Westin Cleveland Downtown
4.0 star property
Downtown Cleveland
8.6 out of 10, Excellent, (1903)
8.6/10
Excellent
(1903)
The price is $109
$109
$128 total
includes taxes & fees
Dec 22 - Dec 23
Hyatt Regency Cleveland At The Arcade
Hyatt Regency Cleveland At The Arcade
4.0 star property
Downtown Cleveland
9.0 out of 10, Wonderful, (1078)
9.0/10
Wonderful
(1078)
The price is $136
$136
$160 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Drury Inn & Suites Cleveland Beachwood
Drury Inn & Suites Cleveland Beachwood
3.0 star property
Orange
9.4 out of 10, Exceptional, (1000)
9.4/10
Exceptional
(1000)
The price is $110
$110
$129 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Hilton Garden Inn Cleveland East/Mayfield Village
Hilton Garden Inn Cleveland East/Mayfield Village
3.0 star property
Mayfield
8.4 out of 10, Very Good, (1002)
8.4/10
Very Good
(1002)
The price is $51
$51
$60 total
includes taxes & fees
Dec 29 - Dec 30
Spark by Hilton Cleveland Beachwood
Spark by Hilton Cleveland Beachwood
3.0 star property
Beachwood
9.2 out of 10, Wonderful, (116)
9.2/10
Wonderful
(116)
The price is $73
$73
$86 total
includes taxes & fees
Dec 25 - Dec 26
Tru By Hilton Cleveland Midtown
Tru By Hilton Cleveland Midtown
2.5 star property
Hough
8.4 out of 10, Very Good, (1501)
8.4/10
Very Good
(1501)
The price is $93
$93
$109 total
includes taxes & fees
Dec 25 - Dec 26
Wyndham Independence
Wyndham Independence
4.0 star property
Independence
6.6 out of 10, (1008)
6.6/10
(1008)
The price is $67
$67
$78 total
includes taxes & fees
Dec 21 - Dec 22
Hampton Inn Cleveland-Downtown
Hampton Inn Cleveland-Downtown
3.0 star property
Downtown Cleveland
8.8 out of 10, Excellent, (1436)
8.8/10
Excellent
(1436)
The price is $74
$74
$86 total
includes taxes & fees
Dec 26 - Dec 27
Drury Plaza Hotel Cleveland Downtown
Drury Plaza Hotel Cleveland Downtown
3.0 star property
Downtown Cleveland
9.4 out of 10, Exceptional, (2634)
9.4/10
Exceptional
(2634)
The price is $128
$128
$150 total
includes taxes & fees
Dec 23 - Dec 24
Holiday Inn Express Cleveland Downtown by IHG
Holiday Inn Express Cleveland Downtown by IHG
2.5 star property
Downtown Cleveland
8.0 out of 10, Very Good, (1690)
8.0/10
Very Good
(1690)
The price is $95
$95
$112 total
includes taxes & fees
Dec 25 - Dec 26
Home2 Suites by Hilton Cleveland Independence
Home2 Suites by Hilton Cleveland Independence
3.0 star property
Independence
8.8 out of 10, Excellent, (669)
8.8/10
Excellent
(669)
The price is $106
$106
$124 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hotel Indigo Cleveland-Beachwood by IHG
Hotel Indigo Cleveland-Beachwood by IHG
3.5 star property
Beachwood
8.2 out of 10, Very Good, (1000)
8.2/10
Very Good
(1000)
The price is $105
$105
$123 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cleveland Marriott East
Cleveland Marriott East
3.5 star property
Warrensville Heights
8.8 out of 10, Excellent, (1000)
8.8/10
Excellent
(1000)
The price is $121
$121
$142 total
includes taxes & fees
Dec 21 - Dec 22
SpringHill Suites by Marriott Cleveland/Solon
SpringHill Suites by Marriott Cleveland/Solon
3.0 star property
Solon
9.0 out of 10, Wonderful, (1010)
9.0/10
Wonderful
(1010)
The price is $110
$110
$129 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Hyatt Place Cleveland/Lyndhurst/Legacy Village
Hyatt Place Cleveland/Lyndhurst/Legacy Village
3.0 star property
Lyndhurst
9.0 out of 10, Wonderful, (1001)
9.0/10
Wonderful
(1001)
The price is $101
$101
$119 total
includes taxes & fees
Dec 28 - Dec 29
Embassy Suites by Hilton Cleveland Rockside
Embassy Suites by Hilton Cleveland Rockside
3.5 star property
Independence
7.4 out of 10, Good, (1000)
7.4/10
Good
(1000)
The price is $118
$118
$139 total
includes taxes & fees
Dec 22 - Dec 23
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, (1000)
7.6/10
Good
(1000)
The price is $81
$81
$93 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Cleveland Downtown
Hilton Cleveland Downtown
4.0 star property
Downtown Cleveland
9.2 out of 10, Wonderful, (1259)
9.2/10
Wonderful
(1259)
The price is $144
$144
$169 total
includes taxes & fees
Dec 26 - Dec 27
Aloft Cleveland Downtown
Aloft Cleveland Downtown
3.0 star property
Downtown Cleveland
8.4 out of 10, Very Good, (1001)
8.4/10
Very Good
(1001)
The price is $110
$110
$129 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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.
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.
Budget hotels in Chesterland and vicinity
7.4 out of 10, Good, (1002)
7.4/10
Good
(1002)
The price is $37
$37
$42 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Econo Lodge Cleveland Southeast - Kent
Econo Lodge Cleveland Southeast - Kent2.0 star property
Streetsboro
7.6 out of 10, Good, (1001)
7.6/10
Good
(1001)
The price is $43
$43
$48 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Super 8 by Wyndham Twinsburg/Cleveland Area
Super 8 by Wyndham Twinsburg/Cleveland Area2.0 star property
Twinsburg
7.0 out of 10, Good, (874)
7.0/10
Good
(874)
The price is $47
$47
$54 total
includes taxes & fees
Dec 28 - Dec 29
Hilton Garden Inn Cleveland East/Mayfield Village
Hilton Garden Inn Cleveland East/Mayfield Village3.0 star property
Mayfield
8.4 out of 10, Very Good, (1002)
8.4/10
Very Good
(1002)
The price is $51
$51
$60 total
includes taxes & fees
Dec 29 - Dec 30
7.2 out of 10, Good, (780)
7.2/10
Good
(780)
The price is $57
$57
$64 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Willow Lodge Willoughby – Cleveland Mentor
Willow Lodge Willoughby – Cleveland Mentor2.0 star property
Willoughby
7.0 out of 10, Good, (917)
7.0/10
Good
(917)
The price is $60
$60
$69 total
includes taxes & fees
Dec 21 - Dec 22
Red Roof Inn Cleveland - Mentor/ Willoughby
Red Roof Inn Cleveland - Mentor/ Willoughby2.0 star property
Willoughby
7.4 out of 10, Good, (1002)
7.4/10
Good
(1002)
The price is $60
$60
$69 total
includes taxes & fees
Dec 22 - Dec 23
Super 8 by Wyndham Mentor/Cleveland Area
Super 8 by Wyndham Mentor/Cleveland Area2.0 star property
Mentor
7.2 out of 10, Good, (965)
7.2/10
Good
(965)
The price is $60
$60
$69 total
includes taxes & fees
Dec 21 - Dec 22
9.2 out of 10, Wonderful, (116)
9.2/10
Wonderful
(116)
The price is $73
$73
$86 total
includes taxes & fees
Dec 25 - Dec 26
8.8 out of 10, Excellent, (1436)
8.8/10
Excellent
(1436)
The price is $74
$74
$86 total
includes taxes & fees
Dec 26 - Dec 27
Hilton Garden Inn Cleveland Downtown
Hilton Garden Inn Cleveland Downtown3.0 star property
Downtown Cleveland
7.4 out of 10, Good, (1000)
7.4/10
Good
(1000)
The price is $77
$77
$90 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Country Inn & Suites by Radisson, Macedonia, OH
Country Inn & Suites by Radisson, Macedonia, OH3.0 star property
Macedonia
7.4 out of 10, Good, (1001)
7.4/10
Good
(1001)
The price is $72
$72
$83 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Holiday Inn Express & Suites Madison by IHG
Holiday Inn Express & Suites Madison by IHG2.5 star property
Madison
9.4 out of 10, Exceptional, (667)
9.4/10
Exceptional
(667)
The price is $78
$78
$90 total
includes taxes & fees
Jan 5 - Jan 6, 2026
8.8 out of 10, Excellent, (792)
8.8/10
Excellent
(792)
The price is $78
$78
$92 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Comfort Inn Independence - Cleveland
Comfort Inn Independence - Cleveland2.5 star property
Independence
7.8 out of 10, Good, (1004)
7.8/10
Good
(1004)
The price is $80
$80
$94 total
includes taxes & fees
Dec 28 - Dec 29
7.6 out of 10, Good, (822)
7.6/10
Good
(822)
The price is $80
$80
$95 total
includes taxes & fees
Dec 22 - Dec 23
La Quinta Inn & Suites by Wyndham Cleveland Macedonia
La Quinta Inn & Suites by Wyndham Cleveland Macedonia3.0 star property
Macedonia
7.6 out of 10, Good, (1000)
7.6/10
Good
(1000)
The price is $81
$81
$93 total
includes taxes & fees
Dec 21 - Dec 22
Extended Stay America Premier Suites - Cleveland - Independence
Extended Stay America Premier Suites - Cleveland - Independence2.5 star property
Independence
7.2 out of 10, Good, (1802)
7.2/10
Good
(1802)
The price is $77
$77
$90 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Hampton Inn & Suites Cleveland/Independence
Hampton Inn & Suites Cleveland/Independence2.5 star property
Independence
8.8 out of 10, Excellent, (1001)
8.8/10
Excellent
(1001)
The price is $89
$89
$105 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Comfort Inn Mayfield Heights Cleveland East
Comfort Inn Mayfield Heights Cleveland East2.5 star property
Mayfield Heights
8.4 out of 10, Very Good, (1002)
8.4/10
Very Good
(1002)
The price is $87
$87
$102 total
includes taxes & fees
Dec 28 - Dec 29
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.
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.
Go beyond your typical stay in Chesterland
Pet friendly
Apartment
Family friendly
Cottage
Top landmarks in Chesterland
Fowler's Mill Golf Course
You might want to practice your swing at Fowler's Mill Golf Course, a golf course located 3.3 mi (5.4 km) from central Chesterland. If Fowler's Mill Golf Course doesn't quite scratch your golfing itch, Berkshire Hill Golf Course, and Pleasant Hill Golf Course are also nearby.
Learn more about Chesterland
Chesterland is well-known for its attractions such as Fowler's Mill Golf Course and Alpine Valley.
Photo by Kristin DePlatchett
Open Photo by Kristin DePlatchett
Check out reviews of Chesterland hotels guests love
Hyatt Regency Cleveland At The Arcade
10/10 Excellent
"Very nice rooms, great gym facilities, loved the historic location, close to downtown attractions."
Tru By Hilton Cleveland Midtown
10/10 Excellent
"Menu fresh sausage undercooked "
Hotel Indigo Cleveland Downtown by IHG
10/10 Excellent
"Great"
Drury Plaza Hotel Cleveland Downtown
10/10 Excellent
"Clean ... friendly staff ... always a great place to stay."
Hilton Garden Inn Cleveland Downtown
10/10 Excellent
"All was excellent except lack of hot water in bath and shower, very disappointing. When i pay for a room i expect hot water."
Fidelity Hotel
10/10 Excellent
"Staff was amazing food was excellent!! Will definitely stay again!"
The Westin Cleveland Downtown
10/10 Excellent
"Nice room, good location, convenient parking garage, friendly staff "
Hilton Cleveland Downtown
10/10 Excellent
"Room was spotless. Property was clean and well decorated. Staff are professional all around."
Wyndham Independence
10/10 Excellent
"Yes everything was great "
Frequently asked questions
What hotels do travelers recommend in Chesterland?
Guests like Hilton Garden Inn Cleveland East/Mayfield Village.
Can I book refundable accommodations in Chesterland?
If you need the flexibility to change your travel plans to Chesterland, most hotels offer refundable* bookable rates. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.
What will the weather in Chesterland be like during my vacation?
The warmest months in Chesterland are usually July and August with an average temp of 68°F. January and February are the chilliest months when the average temp is 31°F. The rainiest months are June and July.
Why should I book my Chesterland accommodation with Hotels.com?
There are plenty of reasons to book your Chesterland travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.