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
$166 nightly
The price is $166
Mar 12 - Mar 13
Total with taxes and fees
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
$166 nightly
The price is $166
Mar 19 - Mar 20
Total with taxes and fees
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.
$226 nightly
The price is $226
Mar 12 - Mar 13
Total with taxes and fees
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
$187 nightly
The price is $189
Mar 12 - Mar 13
Total with taxes and fees
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.
$440 nightly
The price is $459
Mar 15 - Mar 16
Total with taxes and fees
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.
$189 nightly
The price is $189
Mar 12 - Mar 13
Total with taxes and fees
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.
$287 nightly
The price is $287
Mar 12 - Mar 13
Total with taxes and fees
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.
$137 nightly
The price is $137
Mar 16 - Mar 17
Total with taxes and fees
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.
$143 nightly
The price is $151
Mar 12 - Mar 13
Total with taxes and fees
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.
$316 nightly
The price is $338
Mar 18 - Mar 19
Total with taxes and fees
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.
$157 nightly
The price is $162
Mar 12 - Mar 13
Total with taxes and fees
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.
$149 nightly
The price is $154
Mar 16 - Mar 17
Total with taxes and fees
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.
$215 nightly
The price is $215
Mar 19 - Mar 20
Total with taxes and fees
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.
$152 nightly
The price is $159
Mar 15 - Mar 16
Total with taxes and fees
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.
$271 nightly
The price is $287
Mar 18 - Mar 19
Total with taxes and fees
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.
$310 nightly
The price is $336
Mar 13 - Mar 14
Total with taxes and fees
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
$182 nightly
The price is $192
Mar 16 - Mar 17
Total with taxes and fees
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.
$166 nightly
The price is $181
Mar 25 - Mar 26
Total with taxes and fees
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.
$187 nightly
The price is $187
Mar 12 - Mar 13
Total with taxes and fees
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.
$197 nightly
The price is $214
Mar 17 - Mar 18
Total with taxes and fees
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chesterland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $123 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesterland rentals

At Expedia, we put the best Chesterland vacation 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 vacation.

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 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?

Lovely 2 Bedroom Unit with a Hot Tub: This vacation home rental near Chesterland offers a patio, a private yard, 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 the 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 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.