Chesterland Holiday Rentals

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Our top choices for Chesterland holiday 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 AU$235
includes taxes & fees
22 Mar - 23 Mar
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
9.4 out of 10, Exceptional, (6 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 AU$235
includes taxes & fees
19 Mar - 20 Mar
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 AU$311
includes taxes & fees
24 Mar - 25 Mar
Little house on the farm

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$266
includes taxes & fees
24 Mar - 25 Mar
Peaceful private apartment in the charming Hiram countryside

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$673
includes taxes & fees
15 Mar - 16 Mar
Vineyard View | Walk to Wineries & River| Hot Tub

The Gallery House - Art curated by local artist!

The Gallery House - Art curated by local artist!
Cleveland Heights
9.8 out of 10, Exceptional, (7 reviews)
"Me and my husband stayed here for our anniversary weekend. We spent Friday and Saturday touring Cuyahoga Valley NP. From this VRBO it was an easy 20-30 minute drive. The VRBO was clean and comfortable, had everything we needed for a weekend getaway. We cooked breakfast in each morning and walked to the restaurants on Lee street for dinner each evening. The neighborhood was quiet and felt safe. Check in and out were very easy and Mark has been quick to respond to messages the entire time. I would...
United States
Laura M.
The price is AU$274
includes taxes & fees
15 Mar - 16 Mar
The Gallery House - Art curated by local artist!

Willow Woods Retreat - Farmhouse - Patio & Nature

Willow Woods Retreat - Farmhouse - Patio & Nature
Kirtland
9.2 out of 10, Wonderful, (35 reviews)
"Great location, owner communication was wonderful."
United States
Scott M.
The price is AU$411
includes taxes & fees
15 Mar - 16 Mar
Willow Woods Retreat - Farmhouse - Patio & Nature

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, (56 reviews)
"Great option for needing a place to stay while visiting family. "
United States
Katelin B.
The price is AU$196
includes taxes & fees
16 Mar - 17 Mar
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Crisp 2 bedroom upstairs apartment in historic duplex

Crisp 2 bedroom upstairs apartment in historic duplex
Stockyards
10.0 out of 10, Exceptional, (49 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 AU$214
includes taxes & fees
17 Mar - 18 Mar
Crisp 2 bedroom upstairs apartment in historic duplex

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 AU$477
includes taxes & fees
18 Mar - 19 Mar
Cozy Centrally Located Gem-King, Hot Tub, Pets OK, Shops & 15 Mins to Lake Erie

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 AU$229
includes taxes & fees
15 Mar - 16 Mar
Residential Apartment w/Drumkit

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 AU$219
includes taxes & fees
17 Mar - 18 Mar
Nice Apartment next to Christmas Story 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$312
includes taxes & fees
19 Mar - 20 Mar
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, (77 reviews)
"This was a nice, comfortable, and clean apartment. We enjoyed our stay."
United States
Henry W.
The price is AU$226
includes taxes & fees
15 Mar - 16 Mar
Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!

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, (72 reviews)
"It was a very nice property"
United States
Tammy F.
The price is AU$406
includes taxes & fees
18 Mar - 19 Mar
Comfy Updated Historic Gem Pets OK 3B Vibrant Area

Charming Duplex Near Shaker Square Cleveland

Charming Duplex Near Shaker Square Cleveland
Buckeye-Shaker
9.6 out of 10, Exceptional, (5 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$473
includes taxes & fees
13 Mar - 14 Mar
Charming Duplex Near Shaker Square Cleveland

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 AU$269
includes taxes & fees
16 Mar - 17 Mar
Large duplex king size bed and two queen size

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, (68 reviews)
"Great location for a Cleveland visit. Host was responsive and helpful. Will definitely stay again."
United States
Kathleen R.
The price is AU$257
includes taxes & fees
17 Mar - 18 Mar
Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch

Timeless Tremont- Enjoy 20% off 5+ nights

Timeless Tremont- Enjoy 20% off 5+ nights
Tremont
9.4 out of 10, Exceptional, (41 reviews)
"Great location for our visit to Cleveland, would definitely book this unit again in the future."
United States
Jaymie W.
The price is AU$265
includes taxes & fees
17 Mar - 18 Mar
Timeless Tremont- Enjoy 20% off 5+ nights

Modern Victorian Studio: Steps to Cleveland Clinic

Modern Victorian Studio: Steps to Cleveland Clinic
Hough
9.8 out of 10, Exceptional, (8 reviews)
"Clean and modern, pet friendly. Great location, very close to my children’s dorms at CWRU. Plenty of parking. Will definitely stay here again! "
United States
Jessica J.
The price is AU$302
includes taxes & fees
17 Mar - 18 Mar
Modern Victorian Studio: Steps to 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

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$175 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?

Lovely 2 Bedroom Unit with a Hot Tub: This holiday home rental outside of Chesterland offers a patio, a private garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of Access to hot tub 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 Berkshire Hill Golf Course 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.