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Holiday Rentals in Chesterland

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Our top choices for Chesterland holiday rentals

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
10.0 out of 10, Exceptional, (1 review)
"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 €148
includes taxes & fees
13 Jan - 14 Jan
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

Nice Apartment next to Christmas Story House

Nice Apartment next to Christmas Story House
Tremont
9.8 out of 10, Exceptional, (25 reviews)
"We absolutely loved this place ! "
United States
Celeste K.
The price is €137
includes taxes & fees
12 Jan - 13 Jan
Nice Apartment next to Christmas Story House

Charming 2-bedroom Suite with balcony overlooking the Lake in Fairport Harbor

Charming 2-bedroom Suite with balcony overlooking the Lake in Fairport Harbor
2.0 star property
Fairport Harbor
9.4 out of 10, Exceptional, (13 reviews)
"Was very cozy, quiet and well kept. Would stay there again."
United States
Christopher
The price is €153
includes taxes & fees
12 Jan - 13 Jan
Charming 2-bedroom Suite with balcony overlooking the Lake in Fairport Harbor

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, (51 reviews)
"Very nice stay,just as described !!"
United States
Christine K.
The price is €119
includes taxes & fees
12 Jan - 13 Jan
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

10th Floor Downtown High-Rise Gym

10th Floor Downtown High-Rise Gym
2.0 star property
Downtown Cleveland
9.6 out of 10, Exceptional, (4 reviews)
"Amazing stay! Perfect location, very clean, and plenty of space. The host was quick to respond and extremely helpful, which made everything smooth and stress-free. Highly recommend!"
United States
Angelina
The price is €153
includes taxes & fees
12 Jan - 13 Jan
10th Floor Downtown High-Rise Gym

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, (61 reviews)
"Great location. Host was very responsive. This unit is comfortable, well stocked and was perfect for our trip to Cleveland Clinic!"
United States
Anonymous traveller
Classic near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch

Crisp 2 bedroom upstairs apartment in historic duplex

Crisp 2 bedroom upstairs apartment in historic duplex
Stockyards
10.0 out of 10, Exceptional, (47 reviews)
"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 €134
includes taxes & fees
12 Jan - 13 Jan
Crisp 2 bedroom upstairs apartment in historic duplex

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.
Little house on the farm

Cozy CLE: Enjoy 15% Off 3+ Jan Nights! Easy Access to Clinic, Case, Downtown!

Cozy CLE: Enjoy 15% Off 3+ Jan Nights! Easy Access to Clinic, Case, Downtown!
Cleveland Heights
9.2 out of 10, Wonderful, (31 reviews)
"Clean, very comfortable bed, and great location+dining options!"
United States
Noah
The price is €129
includes taxes & fees
12 Jan - 13 Jan
Cozy CLE: Enjoy 15% Off 3+ Jan Nights! Easy Access to Clinic, Case, Downtown!

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 €147
includes taxes & fees
19 Jan - 20 Jan
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat

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 €167
includes taxes & fees
12 Jan - 13 Jan
Peaceful private apartment in the charming Hiram countryside

Coastal Lake Erie Cottage w/ Amazing Water Views!

Coastal Lake Erie Cottage w/ Amazing Water Views!
3.0 star property
Euclid
The price is €179
includes taxes & fees
12 Jan - 13 Jan
Coastal Lake Erie Cottage w/ Amazing Water Views!

Luxe Flat w/ Heated Pool & Sauna • Gym•Heart of DT

Luxe Flat w/ Heated Pool & Sauna • Gym•Heart of DT
2.5 star property
Downtown Cleveland
10.0 out of 10, Exceptional, (1 review)
"Room was very spacious and clean. Check in and check out instructions were easy to follow. The location was just perfect too. The athletic club on the 12th floor was clean and easily accessible and the building was full of history! Highly recommend, will be coming back!"
United States
Jason
The price is €168
includes taxes & fees
26 Jan - 27 Jan
Luxe Flat w/ Heated Pool & Sauna • Gym•Heart of DT

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 €143
includes taxes & fees
12 Jan - 13 Jan
Residential Apartment w/Drumkit

Welcome to the Sandcastle Suite

Welcome to the Sandcastle Suite
Fairport Harbor
10.0 out of 10, Exceptional, (27 reviews)
"I stayed here for business, but it felt like a mini vacation."
United States
Laura
The price is €131
includes taxes & fees
12 Jan - 13 Jan
Welcome to the Sandcastle Suite

1br-1bth- Furnished Apartment in Chardon

1br-1bth- Furnished Apartment in Chardon
Chardon
9.8 out of 10, Exceptional, (10 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 €141
includes taxes & fees
28 Jan - 29 Jan
1br-1bth- Furnished Apartment in Chardon

Charming Spacious & Affordable. Gem of Parma! Modern space superbly clean.

Charming Spacious & Affordable. Gem of Parma! Modern space superbly clean.
2.0 star property
Parma
10.0 out of 10, Exceptional, (12 reviews)
"Great property in a great location. "
United States
Susan K.
The price is €174
includes taxes & fees
12 Jan - 13 Jan
Charming Spacious & Affordable. Gem of Parma! Modern space superbly clean.

Victorian Studio Steps from Cleveland Clinic

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

Renovated Downtown Condo in the HEART OF IT ALL

Renovated Downtown Condo in the HEART OF IT ALL
2.0 star property
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 €167
includes taxes & fees
12 Jan - 13 Jan
Renovated Downtown Condo in the HEART OF IT ALL

Casual CLE: 15% off 3+ Nights + free late checkout

Casual CLE: 15% off 3+ Nights + free late checkout
Tremont
8.8 out of 10, Excellent, (10 reviews)
"Great little comfortable spot. Host was very responsive and helpful. Highly recommend. "
United States
Erin
The price is €159
includes taxes & fees
12 Jan - 13 Jan
Casual CLE: 15% off 3+ Nights + free late checkout
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 €106 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?

Luxury Downtown Townhome w/ Private Garage Unit 4: 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. 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.