A wooden bridge over a snow-covered path in a forest.

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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Chesterland vacation rentals

A wooden two-story building with a balcony, a front door, and a sign that says "OPEN".

1. 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, (71 reviews)
"Really nice place to stay."
United States
Phillip
$159 nightly
The price is $159
Oct 5 - Oct 6
Total with taxes and fees
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
A hallway with a white wall, a wooden floor, a white counter, and a chandelier.

2. Willow Woods Retreat - Farmhouse - Patio & Nature

Willow Woods Retreat - Farmhouse - Patio & Nature
Kirtland
9.2 out of 10, Wonderful, (43 reviews)
"We enjoyed our stay and the accommodations were as expected."
United States
Cherylee L.
$295 nightly
The price is $295
Oct 5 - Oct 6
Total with taxes and fees
Willow Woods Retreat - Farmhouse - Patio & Nature
A wooden deck with two metal chairs and a small round table.

3. Cozy Country Apartment in Heart of Geauga County

Cozy Country Apartment in Heart of Geauga County
Newbury
10.0 out of 10, Exceptional, (33 reviews)
"The apartment was clean, well maintained, and family friendly. Molly was a great host!"
United States
Phillip R.
$277 nightly
The price is $277
Oct 5 - Oct 6
Total with taxes and fees
Cozy Country Apartment in Heart of Geauga County
A wooden cabin with a large dining table and benches, surrounded by large windows offering a view of the forest.

4. Pine Lake Trout Club Cabin #8!!!

Pine Lake Trout Club Cabin #8!!!
Chagrin Falls
8.8 out of 10, Excellent, (15 reviews)
"I loved this place and will definitely be back in the fall. I have already booked another time in October. Very peaceful and tranquil. The cabin had everything anyone would need. Wonderful getaway."
United States
Jeff
$195 nightly
The price is $195
Oct 7 - Oct 8
Total with taxes and fees
Pine Lake Trout Club Cabin #8!!!
A bedroom with a large bed, a hanging plant, and a mirror.

5. Cozy studio near Cleve Clinic, Case

Cozy studio near Cleve Clinic, Case
Cleveland Heights
9.6 out of 10, Exceptional, (5 reviews)
"Good location. Great bakery nearby."
United States
Melvin H.
$159 nightly
The price is $159
Oct 8 - Oct 9
Total with taxes and fees
Cozy studio near Cleve Clinic, Case
A two-story house with a front porch, a small garden, and a wooden deck.

6. Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (99 reviews)
"Great location to enjoy some peaceful country living!"
United States
Jerry L.
$229 nightly
The price is $229
Oct 5 - Oct 6
Total with taxes and fees
Little house on the farm
A living room with a sofa, a coffee table, a fireplace, and artwork on the wall.

7. The Gallery House - Art curated by local artist!

The Gallery House - Art curated by local artist!
Cleveland Heights
9.6 out of 10, Exceptional, (9 reviews)
"Everything was great. I will be back!"
United States
David T.
$212 nightly
The price is $212
Oct 6 - Oct 7
Total with taxes and fees
The Gallery House - Art curated by local artist!
A modern living room with a flat-screen TV mounted on a wall, a wooden entertainment center, and a zebra-patterned rug.

8. Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out

Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
Cleveland Heights
9.0 out of 10, Wonderful, (27 reviews)
"Excellent walkable location. Good for one night in town for an event."
United States
Whitney
$160 nightly
The price is $162
Oct 5 - Oct 6
Total with taxes and fees
Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
A grassy area with two Adirondack chairs and a fire pit, overlooking a body of water.

9. Coastal Lake Erie Cottage w/ Amazing Water Views!

Coastal Lake Erie Cottage w/ Amazing Water Views!
3.0 star property
Euclid
10.0 out of 10, Exceptional, (2 reviews)
"loved the water view but not so fond of the apartment building next door"
United States
gregory
$228 nightly
The price is $243
Oct 8 - Oct 9
Total with taxes and fees
Coastal Lake Erie Cottage w/ Amazing Water Views!
A house with a white picket fence, a red door, and a brick pathway leading to the entrance.

10. Farmhouse of Stoneycreek Acres, our Family Farm

Farmhouse of Stoneycreek Acres, our Family Farm
Newbury
9.8 out of 10, Exceptional, (22 reviews)
"We had a great time at our stay! The house was so cute and cozy, it had everything we needed stocked, and the owner was so friendly through the whole process. Would absolutely stay here again!"
United States
Madison S.
$514 nightly
The price is $514
Oct 5 - Oct 6
Total with taxes and fees
Farmhouse of Stoneycreek Acres, our Family Farm
A modern bedroom with a loft bed, a sofa, and a coffee table.

11. Modern Victorian Studio -Steps to Cleveland Clinic

Modern Victorian Studio -Steps to Cleveland Clinic
Hough
10.0 out of 10, Exceptional, (18 reviews)
"Great location near Cleveland Clinic. Very clean room with free parking onsite."
United States
Mike
$203 nightly
The price is $220
Oct 12 - Oct 13
Total with taxes and fees
Modern Victorian Studio -Steps to Cleveland Clinic
A sunset view from a park bench overlooking a body of water.

12. Residential Apartment w/Drumkit

Residential Apartment w/Drumkit
Willowick
10.0 out of 10, Exceptional, (21 reviews)
"We very much enjoyed our stay. The apartment is a good size, clean, and in a great location. The furnishings were comfortable and we had the supplies we needed. Thank you John."
United States
Brad J.
$169 nightly
The price is $174
Oct 5 - Oct 6
Total with taxes and fees
Residential Apartment w/Drumkit
A bedroom with a green wall, a bed with white and green pillows, and four framed pictures.

13. Little Italy Gem | King Bed, Gym & Free Parking

Little Italy Gem | King Bed, Gym & Free Parking
University Circle
9.6 out of 10, Exceptional, (5 reviews)
"Amazing place to stay"
United States
Anonymous traveler
Little Italy Gem | King Bed, Gym & Free Parking
A garden with a wooden arbor and various plants, a green shed in the background, and a gravel path.

14. The Thistle House off Chardon Square

The Thistle House off Chardon Square
Chardon
10.0 out of 10, Exceptional, (48 reviews)
"Totally charming, great kitchen. Excellent access to all that Chardon has to offer. We were there only a short time but the beach was stupendous. Felt welcoming and historic . . . Would recommend."
United States
Pamela
$537 nightly
The price is $537
Oct 5 - Oct 6
Total with taxes and fees
The Thistle House off Chardon Square
A dining area with a dark wooden table, four chairs, and a decorative centerpiece.

15. Classic Meets Contemporary I Minutes to Cle Clinic

Classic Meets Contemporary I Minutes to Cle Clinic
Cleveland Heights
9.6 out of 10, Exceptional, (14 reviews)
"House was very clean and cozy. Great location."
United States
Monica
$199 nightly
The price is $199
Oct 25 - Oct 26
Total with taxes and fees
Classic Meets Contemporary I Minutes to Cle Clinic
A log cabin with a porch and a small deck, surrounded by a forest.

16. Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.

Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.
Burton
10.0 out of 10, Exceptional, (9 reviews)
"My friends and I had a great stay at the cabins in newberry axel is very kind and the property is very nice"
United States
David H.
$257 nightly
The price is $257
Oct 5 - Oct 6
Total with taxes and fees
Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.
A modern living room with a blue sofa, a coffee table, and a kitchen area with a bar and stools.

17. Upscale Little Italy 2BR | Private Drive & Patio

Upscale Little Italy 2BR | Private Drive & Patio
University Circle
9.4 out of 10, Exceptional, (12 reviews)
"Great location"
United States
Sandra S.
$207 nightly
The price is $224
Oct 5 - Oct 6
Total with taxes and fees
Upscale Little Italy 2BR | Private Drive & Patio
A sign for Cleveland Metroparks at Edgewater Beach.

18. CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC

CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC
Goodrich-Kirtland Park
8.6 out of 10, Excellent, (55 reviews)
"Everything as described! Great stay!"
United States
Billy M.
$138 nightly
The price is $138
Oct 26 - Oct 27
Total with taxes and fees
CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC
A modern kitchen with a wooden countertop, stainless steel sink, and a black refrigerator.

19. Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside
Garrettsville
9.4 out of 10, Exceptional, (6 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
$189 nightly
The price is $191
Oct 5 - Oct 6
Total with taxes and fees
Peaceful private apartment in the charming Hiram countryside
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterland Hotel Reviews

Extended Stay America Premier Suites - Cleveland - Independence

Extended Stay America Premier Suites - Cleveland - Independence

10/10 Excellent
"Great property to stay at if you aren’t wanting to be right in downtown Cleveland. Staff is always friendly and easy to access main roads."
Justin 1-night trip
Posted 8 hours ago
Extended Stay America Premier Suites - Cleveland - Independence

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 $138 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?

Charm 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. Alpine Valley 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.