Chesterland Vacation Rentals

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Our top choices for Chesterland vacation rentals

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
9.4 out of 10, Exceptional, (3 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 CA $199
CA $226 total
includes taxes & fees
Feb 24 - Feb 25
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat

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
9.2 out of 10, Wonderful, (5 reviews)
"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 CA $199
CA $226 total
includes taxes & fees
Feb 24 - Feb 25
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (94 reviews)
"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 CA $211
CA $310 total
includes taxes & fees
Mar 5 - Mar 6
Little house on the farm

Cozy Centrally Located Gem-King, Hot Tub, Pets OK, Shops & 15 Mins to Lake Erie

Cozy Centrally Located Gem-King, Hot Tub, Pets OK, Shops & 15 Mins to Lake Erie
Mentor
10.0 out of 10, Exceptional, (77 reviews)
"The space was exactly as listed except the beds are soooooo comfy!!!! The location was excellent. "
United States
Jessie C.
The price is CA $174
CA $416 total
includes taxes & fees
Feb 17 - Feb 18
Cozy Centrally Located Gem-King, Hot Tub, Pets OK, Shops & 15 Mins to Lake Erie

Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside
Garrettsville
10.0 out of 10, Exceptional, (3 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 CA $123
CA $257 total
includes taxes & fees
Feb 17 - Feb 18
Peaceful private apartment in the charming Hiram countryside

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, (55 reviews)
"Very nice stay,just as described !!"
United States
Christine K.
The price is CA $124
CA $192 total
includes taxes & fees
Feb 17 - Feb 18
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

The House Hotels - Superior Road

The House Hotels - Superior Road
Cleveland Heights
9.4 out of 10, Exceptional, (18 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 CA $150
CA $304 total
includes taxes & fees
Feb 17 - Feb 18
The House Hotels - Superior Road

Historic District 2BR on 1st Floor near Cleveland Clinic ~ Family Friendly ~Safe

Historic District 2BR on 1st Floor near Cleveland Clinic ~ Family Friendly ~Safe
Shaker Heights
9.8 out of 10, Exceptional, (8 reviews)
"Lovely house, wonderful beds and great host."
United States
Cheryl H.
Historic District 2BR on 1st Floor near Cleveland Clinic ~ Family Friendly ~Safe

Classic near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch

Classic near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch
Buckeye-Shaker
9.8 out of 10, Exceptional, (64 reviews)
"Great place to stay . Close to many restaurants and also close to hospital . Ken is an excellent host."
United States
Cheryl C.
The price is CA $98
CA $217 total
includes taxes & fees
Feb 22 - Feb 23
Classic near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch

1br-1bth- Furnished Apartment in Chardon

1br-1bth- Furnished Apartment in Chardon
Chardon
9.6 out of 10, Exceptional, (11 reviews)
"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 CA $135
CA $203 total
includes taxes & fees
Feb 23 - Feb 24
1br-1bth- Furnished Apartment in Chardon

Nice Apartment next to Christmas Story House

Nice Apartment next to Christmas Story House
Tremont
9.8 out of 10, Exceptional, (27 reviews)
"We absolutely loved this place ! "
United States
Celeste K.
The price is CA $80
CA $210 total
includes taxes & fees
Feb 15 - Feb 16
Nice Apartment next to Christmas Story House

Crisp 2 bedroom upstairs apartment in historic duplex

Crisp 2 bedroom upstairs apartment in historic duplex
Stockyards
10.0 out of 10, Exceptional, (48 reviews)
"The place was perfect for a girls weekend! Smooth check in and great location. I would definitely stay here again. "
United States
Kimberly M.
The price is CA $133
CA $205 total
includes taxes & fees
Feb 17 - Feb 18
Crisp 2 bedroom upstairs apartment in historic duplex

Residential Apartment w/Drumkit

Residential Apartment w/Drumkit
Willowick
10.0 out of 10, Exceptional, (18 reviews)
"Great, quiet place! "
United States
Ranae K.
The price is CA $128
CA $220 total
includes taxes & fees
Feb 17 - Feb 18
Residential Apartment w/Drumkit

Large duplex king size bed and two queen size

Large duplex king size bed and two queen size
Cleveland Heights
9.2 out of 10, Wonderful, (67 reviews)
"The house was very nice"
United States
William
The price is CA $136
CA $229 total
includes taxes & fees
Feb 17 - Feb 18
Large duplex king size bed and two queen size

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 CA $379
CA $631 total
includes taxes & fees
Feb 15 - Feb 16
Vineyard View | Walk to Wineries & River| Hot Tub

Timeless Tremont- Enjoy 20% off 5+ nights

Timeless Tremont- Enjoy 20% off 5+ nights
Tremont
9.4 out of 10, Exceptional, (37 reviews)
"Lovely stay in a cute neighborhood within easy walking distance of coffee and restaurants. "
United States
Ashley P.
The price is CA $98
CA $245 total
includes taxes & fees
Feb 17 - Feb 18
Timeless Tremont- Enjoy 20% off 5+ nights

"Gull Cottage" - Lake Erie waterfront - Expansive Views, Historic Cottage Charm

"Gull Cottage" - Lake Erie waterfront - Expansive Views, Historic Cottage Charm
Mentor-on-the-Lake
10.0 out of 10, Exceptional, (65 reviews)
"Great location and beautiful property.!!"
United States
Jodi W.
The price is CA $368
CA $737 total
includes taxes & fees
Feb 17 - Feb 18
"Gull Cottage" - Lake Erie waterfront - Expansive Views, Historic Cottage Charm

Welcome to the Sandcastle Suite

Welcome to the Sandcastle Suite
Fairport Harbor
10.0 out of 10, Exceptional, (27 reviews)
"Great place to stay! the property owner was very responsive. Beautiful area."
United States
Kelsey J.
The price is CA $174
CA $201 total
includes taxes & fees
Feb 17 - Feb 18
Welcome to the Sandcastle Suite

Renovated Downtown Condo in the HEART OF IT ALL

Renovated Downtown Condo in the HEART OF IT ALL
Downtown Cleveland
10.0 out of 10, Exceptional, (3 reviews)
"This is a great spot in nice area of town. It is perfect for a single person or a couple. Nice large windows, that open yay. Comfortable bed, great couch set up. Thanks for a great stay."
United States
Chris B.
The price is CA $102
CA $238 total
includes taxes & fees
Feb 17 - Feb 18
Renovated Downtown Condo in the HEART OF IT ALL

Cozy Victorian Studio Steps from Cleveland Clinic

Cozy Victorian Studio Steps from Cleveland Clinic
Hough
10.0 out of 10, Exceptional, (1 review)
The price is CA $116
CA $295 total
includes taxes & fees
Feb 17 - Feb 18
Cozy Victorian Studio Steps from 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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chesterland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Chesterland?

Yes, you can find vacation rentals close to popular sights in Chesterland, or you can choose a more secluded option if you're looking for relaxation. Chesterland is known for its golf courses and ski areas.

What's the top vacation rental that Chesterland has to offer?

Ohio City Getaway W/ Hot Tub, Pool Table and more!: This vacation home rental near Chesterland is located in the city center and has a fireplace, a furnished patio, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 vacation rentals like in Chesterland?

Vacation rentals are private properties you can book for several days or longer in Chesterland. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family gatherings.