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

Chesterland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Chesterland vacation rentals

A house with a white picket fence, a red door, and a brick pathway leading to the entrance.

1. 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.
The price is ￥49,855
￥81,351 total
includes taxes & fees
Sep 28 - Sep 29
Farmhouse of Stoneycreek Acres, our Family Farm
A garden with a wooden arbor and various plants, a green shed in the background, and a gravel path.

2. 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
The price is ￥52,746
￥84,551 total
includes taxes & fees
Sep 28 - Sep 29
The Thistle House off Chardon Square
A room with large windows, a wooden ceiling, and a view of a grassy outdoor area.

3. Renovated Cottage-Game Room-Fire Pit-Sleeps 8

Renovated Cottage-Game Room-Fire Pit-Sleeps 8
Moreland Hills
9.8 out of 10, Exceptional, (15 reviews)
"Great location and space to visit with family and friends."
United States
Benjamin M.
Renovated Cottage-Game Room-Fire Pit-Sleeps 8
A hallway with a white wall, a wooden floor, a white counter, and a chandelier.

4. Willow Woods Retreat - Farmhouse - Patio & Nature

Willow Woods Retreat - Farmhouse - Patio & Nature
Kirtland
9.2 out of 10, Wonderful, (42 reviews)
"We enjoyed our stay and the accommodations were as expected."
United States
Cherylee L.
The price is ￥17,251
￥45,107 total
includes taxes & fees
Oct 4 - Oct 5
Willow Woods Retreat - Farmhouse - Patio & Nature
A modern kitchen with a central island, bar stools, a window with a view, and a 'DINE' sign on the wall.

5. 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.
Country Cottage Farm Stay at Stoneycreek Acres
A log cabin with a porch and a small deck, surrounded by a forest.

6. 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.
The price is ￥49,855
￥56,977 total
includes taxes & fees
Sep 25 - Sep 26
Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.
A wooden cabin with a large dining table and benches, surrounded by large windows offering a view of the forest.

7. 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
The price is ￥26,767
￥30,703 total
includes taxes & fees
Sep 28 - Sep 29
Pine Lake Trout Club Cabin #8!!!
A wooden deck with two metal chairs and a small round table.

8. 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.
The price is ￥22,949
￥43,841 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Country Apartment in Heart of Geauga County
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
The price is ￥19,625
￥41,520 total
includes taxes & fees
Oct 12 - Oct 13
Coastal Lake Erie Cottage w/ Amazing Water Views!
A wooden two-story building with a balcony, a front door, and a sign that says "OPEN".

10. 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, (69 reviews)
"Really nice place to stay."
United States
Phillip
The price is ￥17,236
￥25,941 total
includes taxes & fees
Sep 29 - Sep 30
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
A dining area with a table and chairs, a kitchen in the background, and a ceiling light fixture.

11. South Euclid Home 10 Minutes to Cleveland Clinic

South Euclid Home 10 Minutes to Cleveland Clinic
South Euclid
9.2 out of 10, Wonderful, (17 reviews)
"Very clean and well maintained property with most everyday essentials provided."
Canada
Thomas
South Euclid Home 10 Minutes to Cleveland Clinic
A modern kitchen with dark cabinetry, a black countertop, and a coffee maker.

12. 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, (82 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.
The price is ￥18,992
￥30,055 total
includes taxes & fees
Sep 28 - Sep 29
Large duplex king size bed and two queen size

13. Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch

Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch
Buckeye-Shaker
9.8 out of 10, Exceptional, (93 reviews)
"Another great stay!"
United States
Paul T.
Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch
A sunset view from a park bench overlooking a body of water.

14. 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.
The price is ￥17,410
￥28,410 total
includes taxes & fees
Sep 28 - Sep 29
Residential Apartment w/Drumkit
An outdoor hot tub area with stone flooring, a brick wall, and string lights.

15. Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!

Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!
University Circle
10.0 out of 10, Exceptional, (88 reviews)
"Great location. Great host."
United States
Mike B.
The price is ￥19,625
￥34,045 total
includes taxes & fees
Oct 4 - Oct 5
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!
A modern kitchen with a central island, bar stools, stainless steel appliances, and pendant lighting.

16. Little Italy! Close to Cleveland Clinic, University Hospital & University Circle

Little Italy! Close to Cleveland Clinic, University Hospital & University Circle
University Circle
10.0 out of 10, Exceptional, (57 reviews)
"This is easily the best place I’ve stayed. Debbie thinks of everything. This was my second time here and looking forward to number 3!"
United States
Connie H.
The price is ￥23,741
￥45,424 total
includes taxes & fees
Oct 25 - Oct 26
Little Italy! Close to Cleveland Clinic, University Hospital & University Circle
A living room with a blue sofa, a wooden coffee table, and a ceiling fan.

17. Center of Little Italy #1

Center of Little Italy #1
University Circle
9.4 out of 10, Exceptional, (20 reviews)
"Great stay and great location!"
United States
Katlyn A.
The price is ￥16,618
￥39,094 total
includes taxes & fees
Oct 20 - Oct 21
Center of Little Italy #1
A bedroom with a bed, a bench, a ceiling fan, a bedside table, a lamp, and a round mirror on the wall.

18. Welcome to the Sandcastle Suite

Welcome to the Sandcastle Suite
Fairport Harbor
9.6 out of 10, Exceptional, (39 reviews)
"We loved the location of the property. It was very clean, and overall great stay with our family. "
United States
Ceaira R.
Welcome to the Sandcastle Suite
An outdoor hot tub area with stone flooring, a brick wall, and string lights.

19. Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!

Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!
University Circle
10.0 out of 10, Exceptional, (72 reviews)
"Awesome place!!"
United States
Quintin B.
The price is ￥19,625
￥34,211 total
includes taxes & fees
Oct 6 - Oct 7
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!
A hallway with a vinyl record on the floor, a lamp, and a wall decorated with vinyl records.

20. Cleveland’s Legends' Lair | Themed | Sleeps 4

Cleveland’s Legends' Lair | Themed | Sleeps 4
North Shore Collinwood
9.6 out of 10, Exceptional, (10 reviews)
"We had a great stay...and it was conveniently located near the beach and downtown Cleveland attractions. "
United States
Rocco W.
Cleveland’s Legends' Lair | Themed | Sleeps 4
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

Wyndham Independence

Wyndham Independence

10/10 Excellent
"Loved the welcoming, friendly staff; the clean, comfortable room; the quiet, refreshed hallway/floor! Everything was great!"
Christine 1-night trip
Posted less than an hour ago
Wyndham Independence

Find out more about Chesterland

Search for holiday rentals in Chesterland on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterland using one of the methods below:

  • View our selection of featured holiday rentals in Chesterland
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Look no further and take a look at our great range of rental properties in Chesterland!

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.