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

Chesterland Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Chesterland holiday rentals

Interior

1. Willow Woods Retreat - Farmhouse - Patio & Nature

Willow Woods Retreat - Farmhouse - Patio & Nature
Kirtland
9.4 out of 10, Exceptional, (41 reviews)
"Very nice stay. "
United States
MichaelLarryBetty S.
The price is HK$1,113
HK$2,570 total
includes taxes & fees
24 Sept - 25 Sept
Willow Woods Retreat - Farmhouse - Patio & Nature
Interior

2. Pine Lake Trout Club Cabin #7!!!

Pine Lake Trout Club Cabin #7!!!
Chagrin Falls
10.0 out of 10, Exceptional, (11 reviews)
"Great spot for a weekend getaway. "
United States
Paul
The price is HK$1,567
HK$1,795 total
includes taxes & fees
7 Sept - 8 Sept
Pine Lake Trout Club Cabin #7!!!
Property grounds

3. The Thistle House off Chardon Square

The Thistle House off Chardon Square
Chardon
10.0 out of 10, Exceptional, (47 reviews)
"This is a charming home and had everything we needed. It is very well appointed, comfortable and a wonderful place to return to."
United States
Brian
The price is HK$2,625
HK$4,208 total
includes taxes & fees
3 Sept - 4 Sept
The Thistle House off Chardon Square
Exterior

4. 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, (65 reviews)
"Wonderful stay. It was clean, nice area, nice view, fun decor. Bed was comfortable. Good privacy."
United States
O'Neill
The price is HK$847
HK$1,286 total
includes taxes & fees
31 Aug - 1 Sept
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Dining

5. Country Cottage Farm Stay at Stoneycreek Acres

Country Cottage Farm Stay at Stoneycreek Acres
Newbury
10.0 out of 10, Exceptional, (75 reviews)
"Excellent communication with host and extremely clean, peaceful and beautiful place to stay "
United States
Jennifer T.
The price is HK$1,559
HK$2,962 total
includes taxes & fees
7 Sept - 8 Sept
Country Cottage Farm Stay at Stoneycreek Acres
Interior

6. Great Group Getaway: Games Galore + Outdoor Oasis

Great Group Getaway: Games Galore + Outdoor Oasis
Painesville
9.8 out of 10, Exceptional, (22 reviews)
"House was perfect for our family. We were in town for a funeral & had plenty of room for several adults & children to stay comfortably in one home. House was clean & well equipped. Very responsive hosts. Would stay again next time in town."
United States
Edward & Carrie S.
The price is HK$2,156
HK$6,296 total
includes taxes & fees
26 Aug - 27 Aug
Great Group Getaway: Games Galore + Outdoor Oasis
Outdoor dining

7. Cozy Country Apartment in Heart of Geauga County

Cozy Country Apartment in Heart of Geauga County
Newbury
10.0 out of 10, Exceptional, (33 reviews)
"The apartment was clean, well maintained, and family friendly. Molly was a great host!"
United States
Phillip R.
The price is HK$1,136
HK$2,194 total
includes taxes & fees
31 Aug - 1 Sept
Cozy Country Apartment in Heart of Geauga County
TV

8. 1br-1bth- Furnished Apartment in Chardon

1br-1bth- Furnished Apartment in Chardon
Chardon
9.6 out of 10, Exceptional, (15 reviews)
"The apartment was very nice and the hosts appointed it very well. It is a great place to stay!"
United States
Eric M.
The price is HK$980
HK$1,215 total
includes taxes & fees
26 Aug - 27 Aug
1br-1bth- Furnished Apartment in Chardon
1 bedroom, free WiFi, bed sheets

9. Welcome to the Sandcastle Suite

Welcome to the Sandcastle Suite
Fairport Harbor
9.6 out of 10, Exceptional, (39 reviews)
"We loved the location of the property. It was very clean, and overall great stay with our family. "
United States
Ceaira R.
The price is HK$1,175
HK$1,720 total
includes taxes & fees
24 Sept - 25 Sept
Welcome to the Sandcastle Suite
Smart TV, fireplace, books

10. Contemporary Coventry: 10% Off 2+Nights+Late Check Out

Contemporary Coventry: 10% Off 2+Nights+Late Check Out
Cleveland
9.0 out of 10, Wonderful, (55 reviews)
"Location was perfect. "
United States
Brian S.
The price is HK$627
HK$1,395 total
includes taxes & fees
1 Sept - 2 Sept
Contemporary Coventry: 10% Off 2+Nights+Late Check Out
Interior

11. Modern & Elegant 2BR | Cleveland Clinic

Modern & Elegant 2BR | Cleveland Clinic
University Circle
10.0 out of 10, Exceptional, (18 reviews)
"Great location and new property"
United States
Vidya
The price is HK$933
HK$2,293 total
includes taxes & fees
26 Aug - 27 Aug
Modern & Elegant 2BR | Cleveland Clinic
Exterior detail

12. Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch

Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch
Buckeye-Shaker
9.8 out of 10, Exceptional, (87 reviews)
"Another great stay!"
United States
Paul T.
The price is HK$656
HK$1,396 total
includes taxes & fees
26 Aug - 27 Aug
Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch
Coffee/tea maker, fridge, microwave, oven

13. Large duplex king size bed and two queen size

Large duplex king size bed and two queen size
Cleveland Heights
9.0 out of 10, Wonderful, (81 reviews)
"The place was great, awesome, close to everything we needed. Thank you for a great place to stay. Plenty of room and bathrooms."
United States
Michelle T.
The price is HK$1,051
HK$1,639 total
includes taxes & fees
20 Sept - 21 Sept
Large duplex king size bed and two queen size
Dining

14. Rest, Relax and Enjoy our Gentleman's Farm in Mantua

Rest, Relax and Enjoy our Gentleman's Farm in Mantua
Mantua
9.6 out of 10, Exceptional, (38 reviews)
"We had a great time here! The kitchen was well-stocked and we enjoyed the beautiful outdoor gardens! We would definitely come back again!"
United States
Dale D.
The price is HK$1,003
HK$2,045 total
includes taxes & fees
21 Sept - 22 Sept
Rest, Relax and Enjoy our Gentleman's Farm in Mantua
Outdoor spa tub

15. Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!

Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!
University Circle
10.0 out of 10, Exceptional, (88 reviews)
"Perfect place to stay. Clean, everything we needed, and great hot tub. "
United States
Kristy K.
The price is HK$972
HK$1,694 total
includes taxes & fees
27 Aug - 28 Aug
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!
TV

16. The House Hotels - Superior Road

The House Hotels - Superior Road
Cleveland Heights
9.4 out of 10, Exceptional, (22 reviews)
"The house was great for a quick overnight stay and Billy was very responsive answering questions about the house and check-in process. The backyard was large and very accommodating for our two dogs. Would stay again!"
United States
Amy O.
The price is HK$864
HK$1,750 total
includes taxes & fees
1 Sept - 2 Sept
The House Hotels - Superior Road
Exterior

17. Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (97 reviews)
"Great location to enjoy some peaceful country living!"
United States
Jerry L.
The price is HK$1,215
HK$1,795 total
includes taxes & fees
3 Sept - 4 Sept
Little house on the farm
Smart TV, fireplace, books

18. Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out

Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
Cleveland Heights
8.8 out of 10, Excellent, (24 reviews)
"Excellent walkable location. Good for one night in town for an event."
United States
Whitney
The price is HK$627
HK$1,359 total
includes taxes & fees
30 Aug - 31 Aug
Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
Terrace/patio

19. Gorgeous 2 Bed/2 Bath | CLE Clinic | Balcony

Gorgeous 2 Bed/2 Bath | CLE Clinic | Balcony
Hough
8.8 out of 10, Excellent, (13 reviews)
"It was the perfect location to be with my family member having surgery at The Cleveland Clinic. Very clean, safe, and home away from home during a stressful time for my family. Would highly recommend!"
United States
Melissa
The price is HK$776
HK$2,098 total
includes taxes & fees
26 Aug - 27 Aug
Gorgeous 2 Bed/2 Bath | CLE Clinic | Balcony
Dining

20. Charming 3-Bedroom Pet-Friendly Home by Lake Erie

Charming 3-Bedroom Pet-Friendly Home by Lake Erie
Euclid
10.0 out of 10, Exceptional, (9 reviews)
"The property was wonderful and we had a pleasant stay and would stay here again if in the area. "
United States
Terri V.
Charming 3-Bedroom Pet-Friendly Home by Lake Erie
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

Hilton Cleveland Downtown

Hilton Cleveland Downtown

8/10 Good
"The room was clean. I was happy to have a shower cap. The pool water was cloudy. Didn’t look clean. The staff was helpful. Shaq at the lounge was very nice and helpful. One front desk male was not so courteous and his long unkept fingernails grossed me out."
Raimundo 1-night trip
Posted 1 hour ago
Hilton Cleveland Downtown

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?

Lovely 2 Bedroom Unit with a Hot Tub: This holiday home rental outside of Chesterland offers a patio, a private garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of Access to hot tub in this rental home to help you unwind.

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. Berkshire Hill Golf Course and Fowler's Mill Golf Course 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.