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Holiday Rentals in Chesterland

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Our top choices for Chesterland holiday rentals

1. Willow Woods Retreat - Farmhouse - Patio & Nature

Willow Woods Retreat - Farmhouse - Patio & Nature
Kirtland
9.2 out of 10, Wonderful, (44 reviews)
"We enjoyed our stay and the accommodations were as expected."
United States
Cherylee L.
The price is €257
includes taxes & fees
22 Oct - 23 Oct
Willow Woods Retreat - Farmhouse - Patio & Nature

2. 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, (72 reviews)
"Really nice place to stay."
United States
Phillip
The price is €149
includes taxes & fees
27 Oct - 28 Oct
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

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

Pine Lake Trout Club Cabin #8!!!
Chagrin Falls
9.0 out of 10, Wonderful, (16 reviews)
"I love staying at this cabin. It is perfect for a weekend getaway. Very cozy with good accommodations."
United States
Jeff
The price is €176
includes taxes & fees
4 Nov - 5 Nov
Pine Lake Trout Club Cabin #8!!!

4. 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 €253
includes taxes & fees
22 Oct - 23 Oct
Cozy Country Apartment in Heart of Geauga County

5. Residential Apartment w/Drumkit

Residential Apartment w/Drumkit
Willowick
10.0 out of 10, Exceptional, (22 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.
Residential Apartment w/Drumkit

6. 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 €449
includes taxes & fees
4 Nov - 5 Nov
Farmhouse of Stoneycreek Acres, our Family Farm

7. 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 €221
includes taxes & fees
16 Nov - 17 Nov
Coastal Lake Erie Cottage w/ Amazing Water Views!

8. 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 €184
includes taxes & fees
26 Oct - 27 Oct
The Gallery House - Art curated by local artist!

9. Contemporary Coventry

Contemporary Coventry
Cleveland
8.8 out of 10, Excellent, (61 reviews)
"Location was perfect. "
United States
Brian S.
The price is €162
includes taxes & fees
27 Oct - 28 Oct
Contemporary Coventry

10. Country Cottage Farm Stay at Stoneycreek Acres

Country Cottage Farm Stay at Stoneycreek Acres
Newbury
10.0 out of 10, Exceptional, (76 reviews)
"Molly and Dave were so friendly and ready to help us with whatever we needed. We felt so welcomed and the cottage was very clean and cozy. It was a great place to come back to and relax. The farm animals were so fun to see out our back windows and as we walked around the property. Will definitely be keeping this on our list to come back too."
United States
Allison M.
The price is €328
includes taxes & fees
4 Nov - 5 Nov
Country Cottage Farm Stay at Stoneycreek Acres

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

Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
Cleveland Heights
9.0 out of 10, Wonderful, (27 reviews)
"Excellent walkable location. Good for one night in town for an event."
United States
Whitney
The price is €153
includes taxes & fees
22 Oct - 23 Oct
Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out

12. 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

13. 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 €232
includes taxes & fees
22 Oct - 23 Oct
Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.

14. 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, (97 reviews)
"Another great stay!"
United States
Paul T.
The price is €174
includes taxes & fees
30 Oct - 31 Oct
Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch

15. 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 €466
includes taxes & fees
4 Nov - 5 Nov
The Thistle House off Chardon Square

16. Classic Meets Contemporary I Minutes to Cle Clinic

Classic Meets Contemporary I Minutes to Cle Clinic
Cleveland Heights
9.6 out of 10, Exceptional, (14 reviews)
"House was very clean and cozy. Great location."
United States
Monica
The price is €184
includes taxes & fees
26 Oct - 27 Oct
Classic Meets Contemporary I Minutes to Cle Clinic

17. 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, (84 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 €174
includes taxes & fees
27 Oct - 28 Oct
Large duplex king size bed and two queen size

18. Sleek DT Cleveland Apt at City Club

Sleek DT Cleveland Apt at City Club
3.0 star property
Downtown Cleveland
9.2 out of 10, Wonderful, (250 reviews)
"Enjoyed our stay, right downtown and accessible to everything."
United States
Sean
The price is €164
includes taxes & fees
29 Oct - 30 Oct
Sleek DT Cleveland Apt at City Club

19. Great Group Getaway: Games Galore + Outdoor Oasis

Great Group Getaway: Games Galore + Outdoor Oasis
Painesville
9.6 out of 10, Exceptional, (24 reviews)
"This home is absolutely beautiful. Spacious, warm, well stocked and situated perfectly for families. The home is an entertainers dream! Our children enjoyed the indoor entertainment; basketball, pool table and the internet access was a hit! The outdoor space provides entertainment and comfort for us all. If you are looking for a place to stay in northeast Ohio THIS IS IT! The host communicated well. 5 Star rating for sure."
United States
Carla K.
The price is €722
includes taxes & fees
3 Nov - 4 Nov
Great Group Getaway: Games Galore + Outdoor Oasis

20. Modern Victorian Studio -Steps to Cleveland Clinic

Modern Victorian Studio -Steps to Cleveland Clinic
Hough
9.8 out of 10, Exceptional, (20 reviews)
"Great location near Cleveland Clinic. Very clean room with free parking onsite."
United States
Mike
The price is €208
includes taxes & fees
3 Nov - 4 Nov
Modern Victorian Studio -Steps to Cleveland Clinic
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, apart-hotels, 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 favorite 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 depends 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 €121 per night. Entering your travel dates in the search wizard you might find 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. Alpine Valley and Berkshire Hill 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.