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Holiday Rentals in Chesterland

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Holiday Rentals in Chesterland

Holiday Home in Stockyards

10.0 out of 10, Exceptional, (45)
"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 €155
includes taxes & fees
26 Dec - 27 Dec
Crisp 2 bedroom upstairs apartment in historic duplex

Holiday Home in Buckeye-Shaker

9.8 out of 10, Exceptional, (56)
"We had made a prior request that housekeeping avoid scented cleaning products as much as possible (due to allergies and sensitivities of people in our group). We were very pleased with their efforts, and our stay was allergy-free! Also, the host, Ken Love, was very responsive when I had questions/comments during and after our stay."
United States
Patricia
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Apartment in Tremont

2.0 star property
10.0 out of 10, Exceptional, (3)
"it was beautiful apartment, very clean, host Derrick was very helpful, he responded to our text messages immediately. "
United States
Savitha C.
The price is €102
includes taxes & fees
14 Dec - 15 Dec
Charming studio apartment in fantastic Cleveland Tremont area

Apartment in Tremont

9.8 out of 10, Exceptional, (24)
"Nice place to stay. Convenience within a 15-20 minute drive for sight seeing. Christmas house, museum and gift shop are right there. Even with that it is very quiet."
United States
Yvonna
The price is €122
includes taxes & fees
9 Dec - 10 Dec
Nice Apartment next to Christmas Story House

Holiday Home in Hough

10.0 out of 10, Exceptional, (1)
Victorian Studio Steps from Cleveland Clinic

Apartment in University Circle

9.6 out of 10, Exceptional, (13)
"Hosts were super responsive and helpful all along the way. Great stay."
United States
Laurel H.
Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed

Apartment in Burton

10.0 out of 10, Exceptional, (47)
"I have stayed here before and enjoyed it just as much the second time. The place had a lot of charm, was very clean and was very convenient to where I was working. I will stay there again. "
United States
Kathryn
The price is €101
includes taxes & fees
30 Nov - 1 Dec
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Holiday Home in 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 €203
includes taxes & fees
4 Dec - 5 Dec
Little house on the farm

Cottage in Euclid

3.0 star property
The price is €202
includes taxes & fees
9 Dec - 10 Dec
Coastal Lake Erie Cottage w/ Amazing Water Views!

Apartment in 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 €170
includes taxes & fees
5 Dec - 6 Dec
Peaceful private apartment in the charming Hiram countryside

Apartment in 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 €133
includes taxes & fees
8 Dec - 9 Dec
1br-1bth- Furnished Apartment in Chardon

Cottage in Newbury

10.0 out of 10, Exceptional, (70)
"Loved our stay!! Clean and wonderful! "
United States
Amber S.
The price is €294
includes taxes & fees
29 Nov - 30 Nov
Country Cottage Farm Stay at Stoneycreek Acres

Cabin in Madison

10.0 out of 10, Exceptional, (1)
"The property is amazing, as is the cabin. Love the decor. We appreciated the privacy, the hot tub worked great. We also appreciated the fire ring with everything needed to build a fire! We had a lovely visit with a great friend, daughter, and her grandson that live in the area. Thanks for everything!"
United States
Jeannie
The price is €150
includes taxes & fees
2 Dec - 3 Dec
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

Holiday Home in Downtown Cleveland

2.0 star property
9.2 out of 10, Wonderful, (21)
"Location was great for a quick family weekend trip. "
United States
Crystal P.
The price is €149
includes taxes & fees
1 Dec - 2 Dec
Luxury Downtown Townhome w/ Private Garage Unit 16

Cabin in Madison

9.4 out of 10, Exceptional, (3)
"This was an incredible stay for my wife and I. The cleanliness, quietness, and coziness was amazing. We will definitely be back for another anniversary stay. The multiple wineries around also help enhance the stay even more. You’re missing out if you don’t book this cabin. "
United States
Matthew
The price is €159
includes taxes & fees
2 Dec - 3 Dec
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat

Apartment in Ohio City

9.8 out of 10, Exceptional, (30)
"A wonderful place with great amenities! Only problem is that it’s on a noisy street (Friday and Saturday nights). Cute decor and comfortable beds and furniture. "
United States
Peggy J.
Historic Haven Hideaway California King Bed

Apartment in 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 €166
includes taxes & fees
24 Dec - 25 Dec
Casual CLE: Relaxed Stay w/ Late Check Out

Holiday Home in Downtown Cleveland

9.6 out of 10, Exceptional, (37)
"Good location, walkable to sports. "
United States
Michael C.
The price is €149
includes taxes & fees
1 Dec - 2 Dec
Luxury Downtown Townhome w/ Private Garage Unit 14

Holiday Home in Downtown Cleveland

9.6 out of 10, Exceptional, (18)
"This place was perfect for our stay and the garage made it so nice!"
United States
Amber D.
Luxury Downtown Townhome w/ Private Garage Unit 7

Holiday Home in Buckeye-Shaker

9.4 out of 10, Exceptional, (71)
"The hosts were very friendly and responsive. The location to Cleveland Clinic and the porch is a big plus. Would stay here again!"
United States
Lizabeth M.
The price is €142
includes taxes & fees
2 Dec - 3 Dec
Lovely in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!
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 €102 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?

Ohio City Getaway W/ Hot Tub, Pool Table and more!: This holiday home rental outside of Chesterland is located in the city centre, and has a fireplace, a furnished patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.