Chesterland Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chesterland vacation rentals

9.4 out of 10, Exceptional, (13 reviews)
"Was very cozy, quiet and well kept. Would stay there again."
United States
Christopher
$173 nightly
The price is $173
Jan 24 - Jan 25
Total with taxes and fees
Charming 2-bedroom Suite with balcony overlooking the Lake in Fairport Harbor
3.0 star property
8.0 out of 10, Very Good, (2 reviews)
"Great location and neighborhood. Very close to JCU. Went to a concert at the stadium and it worked out great. Host was great with communication and no issues. "
United States
Amy
$211 nightly
The price is $223
Feb 17 - Feb 18
Total with taxes and fees
9 Mi to Cleveland: Home Near Hospitals & Colleges
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
$186 nightly
The price is $188
Jan 25 - Jan 26
Total with taxes and fees
Peaceful private apartment in the charming Hiram countryside
9.8 out of 10, Exceptional, (27 reviews)
"We absolutely loved this place ! "
United States
Celeste K.
$149 nightly
The price is $154
Jan 25 - Jan 26
Total with taxes and fees
Nice Apartment next to Christmas Story House
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
Jan 25 - Jan 26
Total with taxes and fees
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
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
$166 nightly
The price is $166
Jan 26 - Jan 27
Total with taxes and fees
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

Condo in Downtown Cleveland

10th Floor Downtown High-Rise Gym
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
$169 nightly
The price is $169
Jan 26 - Jan 27
Total with taxes and fees
10th Floor Downtown High-Rise Gym
9.6 out of 10, Exceptional, (15 reviews)
"Nice, clean place in a great location. "
United States
John S.
$238 nightly
The price is $258
Jan 24 - Jan 25
Total with taxes and fees
Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed
9.8 out of 10, Exceptional, (62 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 traveler
$152 nightly
The price is $159
Jan 25 - Jan 26
Total with taxes and fees
Classic near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch
10.0 out of 10, Exceptional, (48 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.
$143 nightly
The price is $151
Jan 24 - Jan 25
Total with taxes and fees
Crisp 2 bedroom upstairs apartment in historic duplex

Vacation Home in Buckeye-Shaker

Charming Duplex Near Shaker Square Cleveland
10.0 out of 10, Exceptional, (4 reviews)
"It is a clean, well maintained property. It was very comfortable & it is in a nice neighborhood."
United States
Julie S.
$264 nightly
The price is $286
Feb 1 - Feb 2
Total with taxes and fees
Charming Duplex Near Shaker Square 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
$177 nightly
The price is $191
Jan 26 - Jan 27
Total with taxes and fees
Luxe Flat w/ Heated Pool & Sauna • Gym•Heart of DT
9.0 out of 10, Wonderful, (32 reviews)
"Clean, very comfortable bed, and great location+dining options!"
United States
Noah
$145 nightly
The price is $145
Jan 25 - Jan 26
Total with taxes and fees
Cozy CLE: Enjoy 15% Off 3+ Jan Nights! Easy Access to Clinic, Case, Downtown!

Vacation Home in Middlefield

Little house on the farm
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.
$228 nightly
The price is $228
Jan 24 - Jan 25
Total with taxes and fees
Little house on the farm

Apartment in Willowick

Residential Apartment w/Drumkit
10.0 out of 10, Exceptional, (18 reviews)
"Great, quiet place! "
United States
Ranae K.
$157 nightly
The price is $162
Jan 25 - Jan 26
Total with taxes and fees
Residential Apartment w/Drumkit
10.0 out of 10, Exceptional, (2 reviews)
"Everything was handled very well re: reservation, check-in, check-out. Accommodation was excellent, location in a great part of Cleveland. Had a great experience!"
United States
Stephen E.
$127 nightly
The price is $127
Jan 25 - Jan 26
Total with taxes and fees
Dwntwn Luxe Suite Rock Hall • Casino • Stadiums

Vacation Home in Northfield

Acadia Farms Carriage House
10.0 out of 10, Exceptional, (2 reviews)
"Clean room, beautiful grounds, well equipped kitchen, great location for dog walks! Perfect for our family of four!"
United States
Natalie
$197 nightly
The price is $197
Jan 25 - Jan 26
Total with taxes and fees
Acadia Farms Carriage House

Vacation Home in Downtown Cleveland

Luxury Downtown Townhome w/ Private Garage Unit 7
9.6 out of 10, Exceptional, (18 reviews)
"This place was perfect for our stay and the garage made it so nice!"
United States
Amber D.
$150 nightly
The price is $162
Jan 25 - Jan 26
Total with taxes and fees
Luxury Downtown Townhome w/ Private Garage Unit 7

Vacation Home in Downtown Cleveland

Luxury Downtown Townhome w/ Private Garage Unit 3
9.8 out of 10, Exceptional, (23 reviews)
"Nice townhouse, walking distance to downtown. The garage parking is nice to have. Will stay there again."
United States
Sonny C.
$160 nightly
The price is $173
Feb 4 - Feb 5
Total with taxes and fees
Luxury Downtown Townhome w/ Private Garage Unit 3
10.0 out of 10, Exceptional, (12 reviews)
"Great property in a great location. "
United States
Susan K.
$188 nightly
The price is $198
Jan 25 - Jan 26
Total with taxes and fees
Charming Spacious & Affordable. Gem of Parma! Modern space superbly clean.
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Classic near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch: This vacation home rental near Chesterland offers a balcony, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.