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Chesterland Vacation Rentals

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In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Rentals in Chesterland

Outdoor dining
Crisp 2 bedroom upstairs apartment in historic duplex

Crisp 2 bedroom upstairs apartment in historic duplex

Stockyards
10.0 out of 10, Exceptional, (45)
"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.
$143 nightly
The price is $151
Dec 1 - Dec 2
Total with taxes and fees
Crisp 2 bedroom upstairs apartment in historic duplex
Exterior detail
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Buckeye-Shaker
9.8 out of 10, Exceptional, (56)
"We had made a prior request that housekeeping avoid scented cleaning products as much as possible (due to allergies and sensitivities of people in our group). We were very pleased with their efforts, and our stay was allergy-free! Also, the host, Ken Love, was very responsive when I had questions/comments during and after our stay."
United States
Patricia
$152 nightly
The price is $159
Dec 1 - Dec 2
Total with taxes and fees
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!
1 bedroom, iron/ironing board, WiFi, bed sheets
Charming studio apartment in fantastic Cleveland Tremont area

Charming studio apartment in fantastic Cleveland Tremont area

2.0 star property
Tremont
10.0 out of 10, Exceptional, (3)
"it was beautiful apartment, very clean, host Derrick was very helpful, he responded to our text messages immediately. "
United States
Savitha C.
$113 nightly
The price is $113
Dec 14 - Dec 15
Total with taxes and fees
Charming studio apartment in fantastic Cleveland Tremont area
TV
Nice Apartment next to Christmas Story House

Nice Apartment next to Christmas Story House

Tremont
9.8 out of 10, Exceptional, (24)
"Nice place to stay. Convenience within a 15-20 minute drive for sight seeing. Christmas house, museum and gift shop are right there. Even with that it is very quiet."
United States
Yvonna
$131 nightly
The price is $136
Dec 1 - Dec 2
Total with taxes and fees
Nice Apartment next to Christmas Story House
Fridge, microwave, oven, stovetop
Victorian Studio Steps from Cleveland Clinic

Victorian Studio Steps from Cleveland Clinic

Hough
10.0 out of 10, Exceptional, (1)
$203 nightly
The price is $220
Dec 1 - Dec 2
Total with taxes and fees
Victorian Studio Steps from Cleveland Clinic
Fridge, microwave, oven, stovetop
Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed

Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed

University Circle
9.6 out of 10, Exceptional, (13)
"Hosts were super responsive and helpful all along the way. Great stay."
United States
Laurel H.
$192 nightly
The price is $208
Dec 1 - Dec 2
Total with taxes and fees
Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed
Smart TV
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, (47)
"I have stayed here before and enjoyed it just as much the second time. The place had a lot of charm, was very clean and was very convenient to where I was working. I will stay there again. "
United States
Kathryn
$112 nightly
The price is $112
Dec 1 - Dec 2
Total with taxes and fees
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Exterior detail
Little house on the farm

Little house on the farm

Middlefield
10.0 out of 10, Exceptional, (94)
"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
Dec 8 - Dec 9
Total with taxes and fees
Little house on the farm
Cottage (4 Bedrooms) | Interior
Coastal Lake Erie Cottage w/ Amazing Water Views!

Coastal Lake Erie Cottage w/ Amazing Water Views!

3.0 star property
Euclid
$177 nightly
The price is $186
Dec 5 - Dec 6
Total with taxes and fees
Coastal Lake Erie Cottage w/ Amazing Water Views!
1 bedroom, WiFi, bed sheets
Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside

Garrettsville
10.0 out of 10, Exceptional, (3)
"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
$189 nightly
The price is $191
Dec 5 - Dec 6
Total with taxes and fees
Peaceful private apartment in the charming Hiram countryside
Microwave, coffee/tea maker, cookware/dishes/utensils
1br-1bth- Furnished Apartment in Chardon

1br-1bth- Furnished Apartment in Chardon

Chardon
9.8 out of 10, Exceptional, (10)
"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.
$178 nightly
The price is $178
Dec 1 - Dec 2
Total with taxes and fees
1br-1bth- Furnished Apartment in Chardon
Dining
Country Cottage Farm Stay at Stoneycreek Acres

Country Cottage Farm Stay at Stoneycreek Acres

Newbury
10.0 out of 10, Exceptional, (70)
"Loved our stay!! Clean and wonderful! "
United States
Amber S.
$329 nightly
The price is $329
Dec 1 - Dec 2
Total with taxes and fees
Country Cottage Farm Stay at Stoneycreek Acres
Outdoor spa tub
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)
"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
$168 nightly
The price is $168
Dec 2 - Dec 3
Total with taxes and fees
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
Fridge, microwave, oven, stovetop
Luxury Downtown Townhome w/ Private Garage Unit 16

Luxury Downtown Townhome w/ Private Garage Unit 16

2.0 star property
Downtown Cleveland
9.2 out of 10, Wonderful, (21)
"Location was great for a quick family weekend trip. "
United States
Crystal P.
$150 nightly
The price is $162
Dec 1 - Dec 2
Total with taxes and fees
Luxury Downtown Townhome w/ Private Garage Unit 16
Outdoor spa tub
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)
"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
$168 nightly
The price is $168
Dec 10 - Dec 11
Total with taxes and fees
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
Fridge, microwave, oven, stovetop
Historic Haven Hideaway California King Bed

Historic Haven Hideaway California King Bed

Ohio City
9.8 out of 10, Exceptional, (30)
"A wonderful place with great amenities! Only problem is that it’s on a noisy street (Friday and Saturday nights). Cute decor and comfortable beds and furniture. "
United States
Peggy J.
$212 nightly
The price is $212
Dec 1 - Dec 2
Total with taxes and fees
Historic Haven Hideaway California King Bed
Fridge, microwave, oven, stovetop
Casual CLE: Relaxed Stay w/ Late Check Out

Casual CLE: Relaxed Stay w/ Late Check Out

Tremont
8.8 out of 10, Excellent, (10)
"Great little comfortable spot. Host was very responsive and helpful. Highly recommend. "
United States
Erin
$186 nightly
The price is $186
Dec 1 - Dec 2
Total with taxes and fees
Casual CLE: Relaxed Stay w/ Late Check Out
Fridge, microwave, oven, stovetop
Luxury Downtown Townhome w/ Private Garage Unit 14

Luxury Downtown Townhome w/ Private Garage Unit 14

Downtown Cleveland
9.6 out of 10, Exceptional, (37)
"Good location, walkable to sports. "
United States
Michael C.
$145 nightly
The price is $156
Dec 1 - Dec 2
Total with taxes and fees
Luxury Downtown Townhome w/ Private Garage Unit 14
Fridge, microwave, oven, stovetop
Luxury Downtown Townhome w/ Private Garage Unit 7

Luxury Downtown Townhome w/ Private Garage Unit 7

Downtown Cleveland
9.6 out of 10, Exceptional, (18)
"This place was perfect for our stay and the garage made it so nice!"
United States
Amber D.
$165 nightly
The price is $178
Dec 18 - Dec 19
Total with taxes and fees
Luxury Downtown Townhome w/ Private Garage Unit 7
Property grounds
Lovely in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Lovely in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Buckeye-Shaker
9.4 out of 10, Exceptional, (71)
"The hosts were very friendly and responsive. The location to Cleveland Clinic and the porch is a big plus. Would stay here again!"
United States
Lizabeth M.
$152 nightly
The price is $159
Dec 2 - Dec 3
Total with taxes and fees
Lovely in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!
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

Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

10/10 Excellent
"Awesome place to stay in downtown Cleveland! Room was great, location was awesome. Would stay again "
Mallory 1-night trip
Posted 1 day ago
Kimpton Schofield Hotel by IHG

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 $113 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.

Explore a world of travel with Expedia

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?

Luxury Downtown Townhome w/ Private Garage Unit 11: This vacation home rental near 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 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.