Photo by Kristin DePlatchett

Chesterland Holiday Rentals

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Check prices for these dates

Tonight
27 Dec - 28 Dec
Tomorrow
28 Dec - 29 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Chesterland holiday rentals

1 bedroom, WiFi, bed sheets
Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside
Garrettsville
10.0 out of 10, Exceptional, (3)
"We had a wonderful experience! The bed was very comfortable and the space was beautiful and clean. We enjoyed how quiet the area was and it was perfect for our weekend getaway. We will absolutely be staying here the next time we are out this way!"
United States
Ashley
The price is HK$699
HK$1,483 total
includes taxes & fees
29 Dec - 30 Dec
Peaceful private apartment in the charming Hiram countryside
Outdoor dining
Crisp 2 bedroom upstairs apartment in historic duplex

Crisp 2 bedroom upstairs apartment in historic duplex

Crisp 2 bedroom upstairs apartment in historic duplex
Stockyards
10.0 out of 10, Exceptional, (47)
"Had a great stay here while in Cleveland for a concert. Clean, comfortable, and great location. Would definitely stay again if in the area! "
United States
Ashley F.
The price is HK$762
HK$1,172 total
includes taxes & fees
29 Dec - 30 Dec
Crisp 2 bedroom upstairs apartment in historic duplex
TV
Nice Apartment next to Christmas Story House

Nice Apartment next to Christmas Story House

Nice Apartment next to Christmas Story House
Tremont
9.8 out of 10, Exceptional, (25)
"We absolutely loved this place ! "
United States
Celeste K.
The price is HK$459
HK$1,199 total
includes taxes & fees
5 Jan - 6 Jan 2026
Nice Apartment next to Christmas Story House
Exterior detail
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!
Buckeye-Shaker
9.8 out of 10, Exceptional, (58)
"Great location. Host was very responsive. This unit is comfortable, well stocked and was perfect for our trip to Cleveland Clinic!"
United States
Anonymous traveller
The price is HK$560
HK$1,237 total
includes taxes & fees
30 Dec - 31 Dec
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!
Interior
Coastal Lake Erie Cottage w/ Amazing Water Views!

Coastal Lake Erie Cottage w/ Amazing Water Views!

Coastal Lake Erie Cottage w/ Amazing Water Views!
3.0 star property
Euclid
The price is HK$606
HK$1,619 total
includes taxes & fees
29 Dec - 30 Dec
Coastal Lake Erie Cottage w/ Amazing Water Views!
Exterior detail
Little house on the farm

Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (94)
"My stay here was wonderful! James and Anna were very welcoming and such a clean place when arriving! I love this area as I grew up here and was close to many destinations I had planned. I will definitely be returning again."
United States
Sarah S.
The price is HK$1,205
HK$1,756 total
includes taxes & fees
2 Jan - 3 Jan 2026
Little house on the farm
Fridge, microwave, oven, stovetop
Victorian Studio Steps from Cleveland Clinic

Victorian Studio Steps from Cleveland Clinic

Victorian Studio Steps from Cleveland Clinic
Hough
10.0 out of 10, Exceptional, (1)
The price is HK$696
HK$1,684 total
includes taxes & fees
28 Dec - 29 Dec
Victorian Studio Steps from Cleveland Clinic
Interior
Tranquil Tremont-Stay 4 nights & Enjoy 25% off 5th night

Tranquil Tremont-Stay 4 nights & Enjoy 25% off 5th night

Tranquil Tremont-Stay 4 nights & Enjoy 25% off 5th night
Tremont
8.8 out of 10, Excellent, (13)
"Very nice place. Easy acces and parking."
Canada
Jessica D.
The price is HK$546
HK$1,284 total
includes taxes & fees
3 Jan - 4 Jan 2026
Tranquil Tremont-Stay 4 nights & Enjoy 25% off 5th night
Fridge, microwave, oven, stovetop
Welcome to the Sandcastle Suite

Welcome to the Sandcastle Suite

Welcome to the Sandcastle Suite
Fairport Harbor
10.0 out of 10, Exceptional, (27)
"I stayed here for business, but it felt like a mini vacation."
United States
Laura
The price is HK$995
HK$1,150 total
includes taxes & fees
28 Dec - 29 Dec
Welcome to the Sandcastle Suite
Fridge, microwave, oven, stovetop
Center of Little Italy #1

Center of Little Italy #1

Center of Little Italy #1
University Circle
9.6 out of 10, Exceptional, (16)
"Great location! Super cute place. Owner was very responsive and helpful. "
United States
Maria E.
The price is HK$653
HK$1,509 total
includes taxes & fees
29 Dec - 30 Dec
Center of Little Italy #1
Fridge, microwave, oven, stovetop
Luxury Downtown Townhome w/ Private Garage Unit 14

Luxury Downtown Townhome w/ Private Garage Unit 14

Luxury Downtown Townhome w/ Private Garage Unit 14
Downtown Cleveland
9.6 out of 10, Exceptional, (38)
"Great alternative to a hotel "
United States
Chuck A.
The price is HK$311
HK$1,257 total
includes taxes & fees
29 Dec - 30 Dec
Luxury Downtown Townhome w/ Private Garage Unit 14
Private kitchen
Sunfish Room

Sunfish Room

Sunfish Room
2.0 star property
Fairport Harbor
9.0 out of 10, Wonderful, (17)
"great place and location would stay there again"
United States
DENNIS M.
The price is HK$824
HK$1,173 total
includes taxes & fees
28 Dec - 29 Dec
Sunfish Room
Fridge, microwave, oven, stovetop
Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed

Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed

Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed
University Circle
9.6 out of 10, Exceptional, (14)
"Nice, clean place in a great location. "
United States
John S.
The price is HK$462
HK$1,640 total
includes taxes & fees
4 Jan - 5 Jan 2026
Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed
Fridge, microwave, oven, stovetop
Casual CLE: 10% off 2+ Nights + free late checkout

Casual CLE: 10% off 2+ Nights + free late checkout

Casual CLE: 10% off 2+ Nights + free late checkout
Tremont
8.8 out of 10, Excellent, (10)
"Great little comfortable spot. Host was very responsive and helpful. Highly recommend. "
United States
Erin
The price is HK$622
HK$1,399 total
includes taxes & fees
1 Jan - 2 Jan 2026
Casual CLE: 10% off 2+ Nights + free late checkout
Smart TV
Historic District 1BR on 3rd Floor near Cleveland Clinic ~ Quiet & Safe

Historic District 1BR on 3rd Floor near Cleveland Clinic ~ Quiet & Safe

Historic District 1BR on 3rd Floor near Cleveland Clinic ~ Quiet & Safe
Shaker Heights
9.8 out of 10, Exceptional, (7)
"Clean, Unique, Safe/Quiet "
United States
Will P.
The price is HK$732
HK$1,557 total
includes taxes & fees
3 Jan - 4 Jan 2026
Historic District 1BR on 3rd Floor near Cleveland Clinic ~ Quiet & Safe
1 bedroom, iron/ironing board, WiFi, bed sheets
Charming studio apartment in fantastic Cleveland Tremont area

Charming studio apartment in fantastic Cleveland Tremont area

Charming studio apartment in fantastic Cleveland Tremont area
2.0 star property
Tremont
9.6 out of 10, Exceptional, (5)
The price is HK$427
HK$963 total
includes taxes & fees
26 Jan - 27 Jan 2026
Charming studio apartment in fantastic Cleveland Tremont area
Dining
Country Cottage Farm Stay at Stoneycreek Acres

Country Cottage Farm Stay at Stoneycreek Acres

Country Cottage Farm Stay at Stoneycreek Acres
Newbury
10.0 out of 10, Exceptional, (70)
"An absolutely delightful stay for me, my mother and my daughter. The host and her family were so gracious when we asked to be seen around the farm! I don’t know what was better, the adorable cottage or the hospitality they showed us. Will definitely be staying here again!!"
United States
Christine D.
The price is HK$1,469
HK$2,611 total
includes taxes & fees
30 Dec - 31 Dec
Country Cottage Farm Stay at Stoneycreek Acres
Property grounds
Residential Apartment w/Drumkit

Residential Apartment w/Drumkit

Residential Apartment w/Drumkit
Willowick
10.0 out of 10, Exceptional, (18)
"Cute apartment in a quiet neighborhood!"
United States
Shainna P.
The price is HK$731
HK$1,257 total
includes taxes & fees
28 Dec - 29 Dec
Residential Apartment w/Drumkit
Smart TV
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Burton
10.0 out of 10, Exceptional, (50)
"Very nice stay,just as described !!"
United States
Christine K.
The price is HK$664
HK$1,053 total
includes taxes & fees
4 Jan - 5 Jan 2026
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Microwave, coffee/tea maker, cookware/dishes/utensils
1br-1bth- Furnished Apartment in Chardon

1br-1bth- Furnished Apartment in Chardon

1br-1bth- Furnished Apartment in Chardon
Chardon
9.8 out of 10, Exceptional, (10)
"The place was very clean, well stocked, and easy walking distance into town. Chardon is cute and charming. 10/10 would stay here again!"
United States
alex u.
The price is HK$855
HK$1,243 total
includes taxes & fees
13 Jan - 14 Jan 2026
1br-1bth- Furnished Apartment in Chardon
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.
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Top Chesterland Hotel Reviews

Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

10/10 Excellent
"Clean, large room. The entire staff was so sweet and lovely making the experience even better! "
Elizabeth 1-night trip
Posted 1 day ago
Kimpton Schofield Hotel by IHG

Find out more about Chesterland

Search for holiday rentals in Chesterland on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterland using one of the methods below:

  • View our selection of featured holiday rentals in Chesterland
  • Use the map to find apartments and other holiday homes in the Chesterland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterland while they last

Look no further and take a look at our great range of rental properties in Chesterland!

Frequently asked questions

Are there holiday rentals in Chesterland?

Yes, there are holiday rentals close to the most popular sights in Chesterland, or you can select a more secluded option if you're looking for a relaxing stay. Chesterland is known for its golf courses and ski areas.

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

Luxury Downtown Townhome w/ Private Garage Unit 4: This holiday home rental outside of Chesterland is equipped with a balcony, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Chesterland?

Chagrin River and Chesterland City Park are a couple of lovely local spots to get outside and enjoy nature. Fowler's Mill Golf Course and Alpine Valley are other places to visit while you're in town.

What are holiday rentals like in Chesterland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterland. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a small group gathering.