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Chesterland Holiday Rentals

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Our top choices for Chesterland holiday rentals

1. Farmhouse of Stoneycreek Acres, our Family Farm

Farmhouse of Stoneycreek Acres, our Family Farm
Newbury
9.8 out of 10, Exceptional, (22 reviews)
"We had a great time at our stay! The house was so cute and cozy, it had everything we needed stocked, and the owner was so friendly through the whole process. Would absolutely stay here again!"
United States
Madison S.
The price is AU$717
includes taxes & fees
22 Sept - 23 Sept
Farmhouse of Stoneycreek Acres, our Family Farm

2. Willow Woods Retreat - Farmhouse - Patio & Nature

Willow Woods Retreat - Farmhouse - Patio & Nature
Kirtland
9.2 out of 10, Wonderful, (42 reviews)
"We enjoyed our stay and the accommodations were as expected."
United States
Cherylee L.
The price is AU$442
includes taxes & fees
24 Sept - 25 Sept
Willow Woods Retreat - Farmhouse - Patio & Nature

3. The Thistle House off Chardon Square

The Thistle House off Chardon Square
Chardon
10.0 out of 10, Exceptional, (48 reviews)
"Totally charming, great kitchen. Excellent access to all that Chardon has to offer. We were there only a short time but the beach was stupendous. Felt welcoming and historic . . . Would recommend."
United States
Pamela
The price is AU$748
includes taxes & fees
28 Sept - 29 Sept
The Thistle House off Chardon Square

4. Coastal Lake Erie Cottage w/ Amazing Water Views!

Coastal Lake Erie Cottage w/ Amazing Water Views!
3.0 star property
Euclid
10.0 out of 10, Exceptional, (2 reviews)
"loved the water view but not so fond of the apartment building next door"
United States
gregory
The price is AU$368
includes taxes & fees
5 Oct - 6 Oct
Coastal Lake Erie Cottage w/ Amazing Water Views!

5. Country Cottage Farm Stay at Stoneycreek Acres

Country Cottage Farm Stay at Stoneycreek Acres
Newbury
10.0 out of 10, Exceptional, (76 reviews)
"Excellent communication with host and extremely clean, peaceful and beautiful place to stay "
United States
Jennifer T.
The price is AU$522
includes taxes & fees
22 Sept - 23 Sept
Country Cottage Farm Stay at Stoneycreek Acres

6. Pine Lake Trout Club Cabin #8!!!

Pine Lake Trout Club Cabin #8!!!
Chagrin Falls
8.8 out of 10, Excellent, (15 reviews)
"I loved this place and will definitely be back in the fall. I have already booked another time in October. Very peaceful and tranquil. The cabin had everything anyone would need. Wonderful getaway."
United States
Jeff
The price is AU$274
includes taxes & fees
23 Sept - 24 Sept
Pine Lake Trout Club Cabin #8!!!

7. Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.

Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.
Burton
10.0 out of 10, Exceptional, (9 reviews)
"My friends and I had a great stay at the cabins in newberry axel is very kind and the property is very nice"
United States
David H.
The price is AU$492
includes taxes & fees
23 Sept - 24 Sept
Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.

8. 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, (69 reviews)
"Really nice place to stay."
United States
Phillip
The price is AU$230
includes taxes & fees
22 Sept - 23 Sept
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

9. 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 AU$389
includes taxes & fees
22 Sept - 23 Sept
Cozy Country Apartment in Heart of Geauga County

10. South Euclid Home 10 Minutes to Cleveland Clinic

South Euclid Home 10 Minutes to Cleveland Clinic
South Euclid
9.2 out of 10, Wonderful, (17 reviews)
"Very clean and well maintained property with most everyday essentials provided."
Canada
Thomas
The price is AU$513
includes taxes & fees
27 Sept - 28 Sept
South Euclid Home 10 Minutes to Cleveland Clinic

11. 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, (82 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 AU$262
includes taxes & fees
23 Sept - 24 Sept
Large duplex king size bed and two queen size

12. 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)
"Great location. Great host."
United States
Mike B.
The price is AU$299
includes taxes & fees
22 Sept - 23 Sept
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!

13. Residential Apartment w/Drumkit

Residential Apartment w/Drumkit
Willowick
10.0 out of 10, Exceptional, (21 reviews)
"We very much enjoyed our stay. The apartment is a good size, clean, and in a great location. The furnishings were comfortable and we had the supplies we needed. Thank you John."
United States
Brad J.
The price is AU$253
includes taxes & fees
28 Sept - 29 Sept
Residential Apartment w/Drumkit

14. The Gallery House - Art curated by local artist!

The Gallery House - Art curated by local artist!
Cleveland Heights
9.6 out of 10, Exceptional, (9 reviews)
"Everything was great. I will be back!"
United States
David T.
The price is AU$286
includes taxes & fees
29 Sept - 30 Sept
The Gallery House - Art curated by local artist!

15. Family-friendly 5-Star Rated 19th Century Restored Mansion

Family-friendly 5-Star Rated 19th Century Restored Mansion
Painesville
10.0 out of 10, Exceptional, (36 reviews)
"Wonderful stay @ this location. House is a great option for large families and gatherings. We were very pleased with the overall experience."
United States
Gene T.
The price is AU$1,332
includes taxes & fees
19 Oct - 20 Oct
Family-friendly 5-Star Rated 19th Century Restored Mansion

16. Little Italy! Close to Cleveland Clinic, University Hospital & University Circle

Little Italy! Close to Cleveland Clinic, University Hospital & University Circle
University Circle
10.0 out of 10, Exceptional, (26 reviews)
"Very nice stay"
United States
Ryan W.
The price is AU$398
includes taxes & fees
20 Oct - 21 Oct
Little Italy! Close to Cleveland Clinic, University Hospital & University Circle

17. Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (98 reviews)
"Great location to enjoy some peaceful country living!"
United States
Jerry L.
The price is AU$318
includes taxes & fees
24 Sept - 25 Sept
Little house on the farm

18. 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, (92 reviews)
"Another great stay!"
United States
Paul T.
The price is AU$241
includes taxes & fees
23 Sept - 24 Sept
Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch

19. Upscale Little Italy 2BR | Private Drive & Patio

Upscale Little Italy 2BR | Private Drive & Patio
University Circle
9.4 out of 10, Exceptional, (12 reviews)
"Great location"
United States
Sandra S.
The price is AU$320
includes taxes & fees
27 Sept - 28 Sept
Upscale Little Italy 2BR | Private Drive & Patio

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

Contemporary Coventry: 10% Off 2+Nights+Late Check Out
Cleveland
8.8 out of 10, Excellent, (60 reviews)
"Location was perfect. "
United States
Brian S.
The price is AU$224
includes taxes & fees
22 Sept - 23 Sept
Contemporary Coventry: 10% Off 2+Nights+Late Check Out
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

Find out more about Chesterland

Everything you need to know about Chesterland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesterland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterland holiday rentals we have selected for you start as low as AU$146 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesterland rentals

At Expedia, we put the best Chesterland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesterland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch: This holiday home rental outside of Chesterland offers a balcony, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.