Chesterland Holiday Rentals

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Our top choices for Chesterland holiday rentals

Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (95 reviews)
"Wonderful hosts, made us feel right at home!"
United States
Lynn
The price is AU$317
includes taxes & fees
4 May - 5 May
Little house on the farm

Beautiful cabin situated on wooded land with nice yard clearing and small stream

Beautiful cabin situated on wooded land with nice yard clearing and small stream
Madison
10.0 out of 10, Exceptional, (11 reviews)
"The location was very peaceful and relaxing. We felt at home with nature and enjoyed our time very much!"
United States
Steven B.
The price is AU$239
includes taxes & fees
1 May - 2 May
Beautiful cabin situated on wooded land with nice yard clearing and small stream

Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
Madison
9.4 out of 10, Exceptional, (6 reviews)
"Super clean and cozy cabin! I can’t wait to stay again! "
United States
Alyssa T.
The price is AU$264
includes taxes & fees
3 May - 4 May
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat

Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
Madison
9.6 out of 10, Exceptional, (4 reviews)
"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 AU$264
includes taxes & fees
4 May - 5 May
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat

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, (60 reviews)
"We loved this little place. "
United States
Rolanda R.
The price is AU$221
includes taxes & fees
29 Apr - 30 Apr
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

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, (73 reviews)
"Great location for a Cleveland visit. Host was responsive and helpful. Will definitely stay again."
United States
Kathleen R.
The price is AU$233
includes taxes & fees
29 Apr - 30 Apr
Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch

The View! Hot Tub-Golf Cart-Beaches-Billiards-King-Cottage Retreat Full of Fun

The View! Hot Tub-Golf Cart-Beaches-Billiards-King-Cottage Retreat Full of Fun
Fairport Harbor
10.0 out of 10, Exceptional, (61 reviews)
"Efficient booking, entry, and exit- The space was very clean and thoughtfully staged for a visit. We had a wonderful stay!"
United States
Kimberly P.
The price is AU$537
includes taxes & fees
4 May - 5 May
The View! Hot Tub-Golf Cart-Beaches-Billiards-King-Cottage Retreat Full of Fun

Steps to Cleveland Clinic - Bright Studio

Steps to Cleveland Clinic - Bright Studio
Hough
10.0 out of 10, Exceptional, (2 reviews)
"host was very nice and attentive !"
United States
Trinity D.
The price is AU$302
includes taxes & fees
30 Apr - 1 May
Steps to Cleveland Clinic - Bright Studio

Pine Lake Trout Club Cabin #8!!!

Pine Lake Trout Club Cabin #8!!!
Chagrin Falls
8.8 out of 10, Excellent, (12 reviews)
"I always love staying here! "
United States
Jade R.
The price is AU$270
includes taxes & fees
3 May - 4 May
Pine Lake Trout Club Cabin #8!!!

Comfy Updated Historic Gem Pets OK 3B Vibrant Area

Comfy Updated Historic Gem Pets OK 3B Vibrant Area
Painesville
9.8 out of 10, Exceptional, (73 reviews)
"This location was perfect for our stay while visiting with family during the Christmas season. The host was very responsive and helpful. This location definitely had a home away from home feeling as we felt a warm welcome upon entering the home. "
United States
Patrick T.
The price is AU$390
includes taxes & fees
4 May - 5 May
Comfy Updated Historic Gem Pets OK 3B Vibrant Area

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 AU$357
includes taxes & fees
11 May - 12 May
Rest, Relax and Enjoy our Gentleman's Farm in Mantua

Vineyard View | Walk to Wineries & River| Hot Tub

Vineyard View | Walk to Wineries & River| Hot Tub
Madison
10.0 out of 10, Exceptional, (66 reviews)
"Great amenities and beautiful setting"
United States
Joyce L.
The price is AU$672
includes taxes & fees
29 Apr - 30 Apr
Vineyard View | Walk to Wineries & River| Hot Tub

Eclectic Stay in Waterloo Arts District

Eclectic Stay in Waterloo Arts District
North Shore Collinwood
9.8 out of 10, Exceptional, (12 reviews)
"Very unique place! It was like sleeping in a gallery!"
United States
Leah
The price is AU$249
includes taxes & fees
30 Apr - 1 May
Eclectic Stay in Waterloo Arts District

Timeless Tremont- Enjoy 20% off 5+ nights

Timeless Tremont- Enjoy 20% off 5+ nights
Tremont
9.4 out of 10, Exceptional, (44 reviews)
"excellent property in a wonderful neighborhood, close to downtown "
United States
James
The price is AU$264
includes taxes & fees
29 Apr - 30 Apr
Timeless Tremont- Enjoy 20% off 5+ nights

Welcome to the Sandcastle Suite

Welcome to the Sandcastle Suite
Fairport Harbor
9.8 out of 10, Exceptional, (31 reviews)
"Absolutely LOVE staying at these properties!! We have stayed a few times and it will be our go to for every trip to the area. "
United States
Kelly N.
The price is AU$268
includes taxes & fees
29 Apr - 30 Apr
Welcome to the Sandcastle Suite

Charming Duplex Near Shaker Square Cleveland

Charming Duplex Near Shaker Square Cleveland
Buckeye-Shaker
9.8 out of 10, Exceptional, (7 reviews)
"It is a clean, well maintained property. It was very comfortable & it is in a nice neighborhood."
United States
Julie S.
The price is AU$415
includes taxes & fees
29 Apr - 30 Apr
Charming Duplex Near Shaker Square Cleveland

Acadia Farms Carriage House

Acadia Farms Carriage House
Northfield
9.6 out of 10, Exceptional, (5 reviews)
"Clean room, beautiful grounds, well equipped kitchen, great location for dog walks! Perfect for our family of four!"
United States
Natalie
The price is AU$278
includes taxes & fees
29 Apr - 30 Apr
Acadia Farms Carriage House

The House Hotels - Superior Road

The House Hotels - Superior Road
Cleveland Heights
9.4 out of 10, Exceptional, (20 reviews)
"A beautiful, comfortable, well kept apartment in a great location. This was ous second stay here so you know we like it!"
United States
Steve W.
The price is AU$311
includes taxes & fees
29 Apr - 30 Apr
The House Hotels - Superior Road

Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!

Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!
Buckeye-Shaker
9.4 out of 10, Exceptional, (85 reviews)
"The house is clean the host is always present whenever you needed I enjoyed my stay I can recommend you to book your stay"
United States
TULINAYO T.
The price is AU$224
includes taxes & fees
3 May - 4 May
Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!

Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside
Garrettsville
10.0 out of 10, Exceptional, (4 reviews)
"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 AU$264
includes taxes & fees
6 May - 7 May
Peaceful private apartment in the charming Hiram countryside
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$189 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?

Luxury Downtown Townhome w/ Private Garage Unit 11: This holiday home rental outside of Chesterland is equipped with a balcony, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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. Chester Town Hall and West Geauga Plaza 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.