Chesterland Holiday Rentals from €118: Search Short-Term Rentals

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

Acadia Farms Carriage House : This holiday home rental outside of Chesterland offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of garden in this rental home to help you unwind.

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Our top choices for Chesterland holiday rentals

A house with a white picket fence, a red door, and a brick pathway leading to the entrance.

1. Farmhouse of Stoneycreek Acres, our Family Farm

Newbury

Madison S.

includes taxes & fees

7 Sept - 8 Sept

A garden with a wooden arbor and various plants, a green shed in the background, and a gravel path.

2. The Thistle House off Chardon Square

Chardon

Brian

includes taxes & fees

7 Sept - 8 Sept

A hallway with a white wall, a wooden floor, a white counter, and a chandelier.

3. Willow Woods Retreat - Farmhouse - Patio & Nature

Kirtland

Cherylee L.

includes taxes & fees

13 Sept - 14 Sept

A wooden two-story building with a balcony, a front door, and a sign that says "OPEN".

4. Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Burton

O'Neill

includes taxes & fees

6 Oct - 7 Oct

A modern kitchen with a central island, bar stools, a window with a view, and a 'DINE' sign on the wall.

5. Country Cottage Farm Stay at Stoneycreek Acres

Newbury

Jennifer T.

includes taxes & fees

7 Sept - 8 Sept

A log cabin with a porch and a small deck, surrounded by a forest.

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

Burton

David H.

includes taxes & fees

6 Sept - 7 Sept

A wooden deck with two metal chairs and a small round table.

7. Cozy Country Apartment in Heart of Geauga County

Newbury

Phillip R.

includes taxes & fees

7 Sept - 8 Sept

A wooden cabin with a large dining table and benches, surrounded by large windows offering a view of the forest.

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

Chagrin Falls

Jeff

includes taxes & fees

14 Sept - 15 Sept

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Top Chesterland Hotel Reviews

Drury Plaza Hotel Cleveland Downtown

10/10 Excellent

"It was our first time at this hotel and we were really impressed with how the hotel looked (transformed a former board of education building). The room had high ceilings and very large windows. We could see some historic buildings which get illuminated at night with various colours. The included breakfast and supper was great too. Close proximity to progressive field made it even better."

Hotel Indigo Cleveland Downtown by IHG

8/10 Good

"We really loved our stay here! Overall it exceeded our expectations. It was very convenient to get around downtown. The room was gorgeous as well as the outside courtyard. Our only critique is that we were surprised the rooms did not have a microwave. But other than that we would definitely stay again!"

Comfort Inn Cleveland Downtown

8/10 Good

"This hotel is obviously older than others we've stayed in and does show age, understandably. Very slow, creaky elevators were a bit unnerving. Our room was very clean and the bed was very comfortable as well. A/C (it was 30 degrees Celsius during our couple of days in Cleveland) worked really well for which we were grateful! The included breakfast was wonderful and quickly replenished when needed. We will definitely book here again on our next trip to Cleveland."

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 €118 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?

Acadia Farms Carriage House: This holiday home rental outside of Chesterland offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of garden 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. 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.

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Our top choices for Chesterland holiday rentals