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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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.
$303 nightly
The price is $303
Nov 16 - Nov 17
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, (73 reviews)
"Really nice place to stay."
United States
Phillip
$147 nightly
The price is $147
Nov 9 - Nov 10
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
9.0 out of 10, Wonderful, (16 reviews)
"I love staying at this cabin. It is perfect for a weekend getaway. Very cozy with good accommodations."
United States
Jeff
$180 nightly
The price is $180
Nov 10 - Nov 11
Total with taxes and fees
Pine Lake Trout Club Cabin #8!!!
A sunset view from a park bench overlooking a body of water.

4. 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.
$150 nightly
The price is $155
Nov 9 - Nov 10
Total with taxes and fees
Residential Apartment w/Drumkit
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
$228 nightly
The price is $243
Nov 10 - Nov 11
Total with taxes and fees
Coastal Lake Erie Cottage w/ Amazing Water Views!
A wooden deck with two metal chairs and a small round table.

6. 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.
$265 nightly
The price is $265
Nov 9 - Nov 10
Total with taxes and fees
Cozy Country Apartment in Heart of Geauga County
A modern kitchen with white cabinets, a central island with seating, a microwave, and a refrigerator.

7. Country Cottage Farm Stay at Stoneycreek Acres

Country Cottage Farm Stay at Stoneycreek Acres
Newbury
10.0 out of 10, Exceptional, (76 reviews)
"Excellent communication with host and extremely clean, peaceful and beautiful place to stay "
United States
Jennifer T.
$359 nightly
The price is $359
Nov 9 - Nov 10
Total with taxes and fees
Country Cottage Farm Stay at Stoneycreek Acres
A bathroom with a shower, toilet, and storage shelves.

8. 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 lot of fun getting to see our daughter. The host and their family were great to work with."
United States
333 Therapeutics Consulting L.
$490 nightly
The price is $490
Nov 9 - Nov 10
Total with taxes and fees
Farmhouse of Stoneycreek Acres, our Family Farm
A modern living room with a flat-screen TV, a ceiling fan, and a kitchen area with a sink.

9. Contemporary Coventry

Contemporary Coventry
Cleveland
8.6 out of 10, Excellent, (63 reviews)
"Nice place and very reasonable woth price per night, stayed 5, with close proximity to Cleveland clinic. Felt very safe in the neighborhood, enough to take long walks in the morning."
United States
Cheryl P.
$159 nightly
The price is $159
Nov 9 - Nov 10
Total with taxes and fees
Contemporary Coventry
A dining area with a dark wooden table, four chairs, and a decorative centerpiece.

10. 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
$190 nightly
The price is $190
Nov 9 - Nov 10
Total with taxes and fees
Classic Meets Contemporary I Minutes to Cle Clinic
Living area

11. 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, (264 reviews)
"Enjoyed our stay, right downtown and accessible to everything."
United States
Sean
$243 nightly
The price is $249
Nov 9 - Nov 10
Total with taxes and fees
Sleek DT Cleveland Apt at City Club
A log cabin with a porch and a small deck, surrounded by a forest.

12. 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, (10 reviews)
"Fantastic location for a night either with friends or the family! Plenty of options to entertain with a nice, wide layout.Served VERY nicely for a bachelor party with the pavilion/bar setup!"
United States
Anonymous traveler
$238 nightly
The price is $238
Nov 9 - Nov 10
Total with taxes and fees
Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.
A living room with a sofa, a coffee table, a fireplace, and artwork on the wall.

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

The Gallery House - Art curated by local artist!
Cleveland Heights
9.4 out of 10, Exceptional, (10 reviews)
"Everything was great. I will be back!"
United States
David T.
$203 nightly
The price is $203
Nov 16 - Nov 17
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.

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
$512 nightly
The price is $512
Nov 9 - Nov 10
Total with taxes and fees
The Thistle House off Chardon Square
A wooden cabin interior with a couch, a staircase, and a television.

15. Pine Lake Trout Club Cabin #7!!!

Pine Lake Trout Club Cabin #7!!!
Chagrin Falls
9.8 out of 10, Exceptional, (12 reviews)
"Perfect quiet place."
United States
Marcus R.
$212 nightly
The price is $212
Nov 11 - Nov 12
Total with taxes and fees
Pine Lake Trout Club Cabin #7!!!
A modern living room with a sectional sofa, a coffee table, a small table with a plant, and a floor lamp.

16. Amazing 2-bedroom house with AC in Eastlake

Amazing 2-bedroom house with AC in Eastlake
Eastlake
9.8 out of 10, Exceptional, (17 reviews)
"Smaller home close to restaurants and lake . We really enjoyed our visit."
United States
kelly d.
$255 nightly
The price is $267
Nov 16 - Nov 17
Total with taxes and fees
Amazing 2-bedroom house with AC in Eastlake
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, (85 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.
$169 nightly
The price is $179
Nov 12 - Nov 13
Total with taxes and fees
Large duplex king size bed and two queen size
A modern kitchen with dark wood cabinets, a marble countertop, and pendant lighting.

18. Great Group Getaway: Games Galore + Outdoor Oasis

Great Group Getaway: Games Galore + Outdoor Oasis
Painesville
9.6 out of 10, Exceptional, (25 reviews)
"This home is absolutely beautiful. Spacious, warm, well stocked and situated perfectly for families. The home is an entertainers dream! Our children enjoyed the indoor entertainment; basketball, pool table and the internet access was a hit! The outdoor space provides entertainment and comfort for us all. If you are looking for a place to stay in northeast Ohio THIS IS IT! The host communicated well. 5 Star rating for sure."
United States
Carla K.
$743 nightly
The price is $743
Nov 17 - Nov 18
Total with taxes and fees
Great Group Getaway: Games Galore + Outdoor Oasis
A modern living room with a blue sofa, a coffee table, and a kitchen area with a bar and stools.

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

Upscale Little Italy 2BR | Private Drive & Patio
University Circle
9.6 out of 10, Exceptional, (14 reviews)
"Great location"
United States
Sandra S.
$202 nightly
The price is $220
Nov 9 - Nov 10
Total with taxes and fees
Upscale Little Italy 2BR | Private Drive & Patio
A modern bedroom with a loft bed, a sofa, and a coffee table.

20. 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
$201 nightly
The price is $219
Nov 10 - Nov 11
Total with taxes and fees
Modern Victorian Studio -Steps to Cleveland 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.
View all properties

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
apart-hotel image
Aparthotels
Aparthotels

Top Chesterland Hotel Reviews

A restaurant with wooden booths and tables, featuring signs for 'Chianti' and 'Bardolino'.
Holiday Inn Cleveland-Mayfield by IHG

Holiday Inn Cleveland-Mayfield by IHG

Holiday Inn Cleveland-Mayfield by IHG
Mayfield

10/10 Excellent

Facilities are really nice after their recent renovation. Their location is most convenient and the restaurant downstairs has amazing Italian food. I would stay again!
United States
SIMON
Reviewed June 4, 2023
Holiday Inn Cleveland-Mayfield 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 $227 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.