Chesterland Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Chesterland vacation rentals

House (4 Bedrooms) | Interior

9 Mi to Cleveland: Home Near Hospitals & Colleges

9 Mi to Cleveland: Home Near Hospitals & Colleges
3.0 star property
University Heights
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
$272 nightly
The price is $288
Mar 23 - Mar 24
Total with taxes and fees
9 Mi to Cleveland: Home Near Hospitals & Colleges
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
$197 nightly
The price is $208
Mar 1 - Mar 2
Total with taxes and fees
Coastal Lake Erie Cottage w/ Amazing Water Views!
Apartment (1 Bedroom) | Interior

Waterfront Cleveland Apt ~ 1 Mi to Downtown

Waterfront Cleveland Apt ~ 1 Mi to Downtown
3.0 star property
Downtown Cleveland
2.0 out of 10, (1 review)
$330 nightly
The price is $358
Mar 1 - Mar 2
Total with taxes and fees
Waterfront Cleveland Apt ~ 1 Mi to Downtown
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

Hyatt Regency Cleveland At The Arcade

Hyatt Regency Cleveland At The Arcade

10/10 Excellent
"This hotel was one of the most beautiful hotels I have seen & stayed at. All the staff were professional & friendly. The room I was in was clean, with a great Arcade view. Food & drinks were delicious, as well."
Katherine 1-night trip
Posted 1 day ago
Hyatt Regency Cleveland At The Arcade

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 $127 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.

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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?

Ohio City Getaway W/ Hot Tub, Pool Table and more!: This vacation home rental near Chesterland is located in the city center and has a fireplace, a furnished patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.