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

Chesterland Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chesterland vacation rentals

A hallway with a white wall, a wooden floor, a white counter, and a chandelier.

1. Willow Woods Retreat - Farmhouse - Patio & Nature

Willow Woods Retreat - Farmhouse - Patio & Nature
Kirtland
9.2 out of 10, Wonderful, (44 reviews)
"We enjoyed our stay and the accommodations were as expected."
United States
Cherylee L.
$292 nightly
The price is $292
Oct 19 - Oct 20
Total with taxes and fees
Willow Woods Retreat - Farmhouse - Patio & Nature
A wooden two-story building with a balcony, a front door, and a sign that says "OPEN".

2. 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, (72 reviews)
"Really nice place to stay."
United States
Phillip
$159 nightly
The price is $159
Oct 19 - Oct 20
Total with taxes and fees
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
A wooden cabin with a large dining table and benches, surrounded by large windows offering a view of the forest.

3. 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 19 - Oct 20
Total with taxes and fees
Pine Lake Trout Club Cabin #8!!!
A wooden deck with two metal chairs and a small round table.

4. 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 21 - Oct 22
Total with taxes and fees
Cozy Country Apartment in Heart of Geauga County
A grassy area with two Adirondack chairs and a fire pit, overlooking a body of water.

5. 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
$248 nightly
The price is $264
Nov 16 - Nov 17
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.

6. 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 19 - Oct 20
Total with taxes and fees
Farmhouse of Stoneycreek Acres, our Family Farm
A modern kitchen with a central island, bar stools, a window with a view, and a 'DINE' sign on the wall.

7. Country Cottage Farm Stay at Stoneycreek Acres

Country Cottage Farm Stay at Stoneycreek Acres
Newbury
10.0 out of 10, Exceptional, (76 reviews)
"Molly and Dave were so friendly and ready to help us with whatever we needed. We felt so welcomed and the cottage was very clean and cozy. It was a great place to come back to and relax. The farm animals were so fun to see out our back windows and as we walked around the property. Will definitely be keeping this on our list to come back too."
United States
Allison M.
$378 nightly
The price is $378
Nov 2 - Nov 3
Total with taxes and fees
Country Cottage Farm Stay at Stoneycreek Acres
A sunset view from a park bench overlooking a body of water.

8. Residential Apartment w/Drumkit

Residential Apartment w/Drumkit
Willowick
10.0 out of 10, Exceptional, (22 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.
$162 nightly
The price is $167
Oct 19 - Oct 20
Total with taxes and fees
Residential Apartment w/Drumkit
Living area

9. Sleek DT Cleveland Apt at City Club

Sleek DT Cleveland Apt at City Club
3.0 star property
Downtown Cleveland
9.2 out of 10, Wonderful, (247 reviews)
"Smooth booking and satisfactory stay"
United States
Chad
$195 nightly
The price is $214
Oct 20 - Oct 21
Total with taxes and fees
Sleek DT Cleveland Apt at City Club
A modern living room with a flat-screen TV, a ceiling fan, and a kitchen area with a sink.

10. Contemporary Coventry

Contemporary Coventry
Cleveland
8.8 out of 10, Excellent, (61 reviews)
"Location was perfect. "
United States
Brian S.
$177 nightly
The price is $177
Oct 19 - Oct 20
Total with taxes and fees
Contemporary Coventry
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
9.8 out of 10, Exceptional, (20 reviews)
"Great location near Cleveland Clinic. Very clean room with free parking onsite."
United States
Mike
$205 nightly
The price is $222
Oct 26 - Oct 27
Total with taxes and fees
Modern Victorian Studio -Steps to Cleveland Clinic
A bedroom with a large bed, a hanging plant, and a mirror.

12. 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 22 - Oct 23
Total with taxes and fees
Cozy studio near Cleve Clinic, Case
A log cabin with a porch and a small deck, surrounded by a forest.

13. 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 19 - Oct 20
Total with taxes and fees
Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.
A covered porch with wicker chairs and a blue patterned rug.

14. 2 bedroom apartment in the beautiful Middlefield countryside!

2 bedroom apartment in the beautiful Middlefield countryside!
Middlefield
8.6 out of 10, Excellent, (7 reviews)
"Fantastic clean and easy perfect for our quick trip!"
United States
Ashley B.
$186 nightly
The price is $186
Oct 20 - Oct 21
Total with taxes and fees
2 bedroom apartment in the beautiful Middlefield countryside!
A living room with a sofa, a coffee table, a fireplace, and artwork on the wall.

15. 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.
$199 nightly
The price is $199
Oct 26 - Oct 27
Total with taxes and fees
The Gallery House - Art curated by local artist!
A garden with a wooden arbor and various plants, a green shed in the background, and a gravel path.

16. 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 19 - Oct 20
Total with taxes and fees
The Thistle House off Chardon Square
A modern kitchen with dark cabinetry, a black countertop, and a coffee maker.

17. Large duplex king size bed and two queen size

Large duplex king size bed and two queen size
Cleveland Heights
9.0 out of 10, Wonderful, (84 reviews)
"The place was great, awesome, close to everything we needed. Thank you for a great place to stay. Plenty of room and bathrooms."
United States
Michelle T.
$182 nightly
The price is $192
Oct 19 - Oct 20
Total with taxes and fees
Large duplex king size bed and two queen size
A dining room with a wooden table, six chairs, a chandelier, and a decorative mirror.

18. Charming 3-Bedroom Pet-Friendly Home by Lake Erie

Charming 3-Bedroom Pet-Friendly Home by Lake Erie
Euclid
10.0 out of 10, Exceptional, (9 reviews)
"The property was wonderful and we had a pleasant stay and would stay here again if in the area. "
United States
Terri V.
$220 nightly
The price is $220
Oct 21 - Oct 22
Total with taxes and fees
Charming 3-Bedroom Pet-Friendly Home by Lake Erie
A living room with a sofa, a coffee table, a TV, and a foosball table.

19. Heart of Little Italy- Walk to CWRU & Cleveland Clinic -Free Parking

Heart of Little Italy- Walk to CWRU & Cleveland Clinic -Free Parking
University Circle
9.2 out of 10, Wonderful, (12 reviews)
"I ran into one little hiccup and the host was very responsive and took care of it right away. I would highly recommend this location for its walkability to local sites."
United States
Jaymie
$220 nightly
The price is $220
Oct 18 - Oct 19
Total with taxes and fees
Heart of Little Italy- Walk to CWRU & Cleveland Clinic -Free Parking
A dining area with a dark wooden table, four chairs, and a decorative centerpiece.

20. 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
$183 nightly
The price is $183
Oct 21 - Oct 22
Total with taxes and fees
Classic Meets Contemporary I Minutes to Cle 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

Hyatt Regency Cleveland At The Arcade

Hyatt Regency Cleveland At The Arcade

10/10 Excellent
"We booked last minute for a concert at the Rock & Roll Hall of Fame not realizing there was also a baseball game that night, and also a wedding right at the hotel. The hotel was beautiful, and even my surly 13-year-old agreed. Our room was clean and comfortable, and the staff were personable and attentive. I called housekeeping when I realized there was no shampoo in the bathroom, and someone was there within minutes with a new bottle. The valet service was quick and easy as well. We will definitely come back."
Lindsay 1-night trip
Posted 1 hour 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 $114 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.