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

Our top choices for Chesterland vacation rentals

Exterior detail

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 AED 1,157
AED 1,888 total
includes taxes & fees
28 Sep - 29 Sep
Farmhouse of Stoneycreek Acres, our Family Farm
Property grounds

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 AED 1,230
AED 1,972 total
includes taxes & fees
24 Sep - 25 Sep
The Thistle House off Chardon Square
Interior

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
Interior

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 AED 400
AED 1,047 total
includes taxes & fees
4 Oct - 5 Oct
Willow Woods Retreat - Farmhouse - Patio & Nature
Dining

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
Exterior

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 AED 1,157
AED 1,322 total
includes taxes & fees
24 Sep - 25 Sep
Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.
Dining

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 AED 624
AED 716 total
includes taxes & fees
24 Sep - 25 Sep
Pine Lake Trout Club Cabin #8!!!
Outdoor dining

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 AED 533
AED 1,017 total
includes taxes & fees
24 Sep - 25 Sep
Cozy Country Apartment in Heart of Geauga County
Cottage (4 Bedrooms) | Interior

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 AED 470
AED 979 total
includes taxes & fees
12 Oct - 13 Oct
Coastal Lake Erie Cottage w/ Amazing Water Views!
Exterior

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 AED 400
AED 602 total
includes taxes & fees
29 Sep - 30 Sep
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Dining

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
The price is AED 613
AED 1,327 total
includes taxes & fees
27 Sep - 28 Sep
South Euclid Home 10 Minutes to Cleveland Clinic
Coffee/tea maker, fridge, microwave, oven

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 AED 448
AED 705 total
includes taxes & fees
28 Sep - 29 Sep
Large duplex king size bed and two queen size
Exterior detail

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, (92 reviews)
"Another great stay!"
United States
Paul T.
The price is AED 340
AED 668 total
includes taxes & fees
24 Sep - 25 Sep
Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch
Property grounds

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 AED 404
AED 659 total
includes taxes & fees
28 Sep - 29 Sep
Residential Apartment w/Drumkit
Outdoor spa tub

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 AED 455
AED 790 total
includes taxes & fees
4 Oct - 5 Oct
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!
Coffee/tea maker, fridge, microwave, oven

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, (56 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 AED 514
AED 1,014 total
includes taxes & fees
24 Sep - 25 Sep
Little Italy! Close to Cleveland Clinic, University Hospital & University Circle
Smart TV

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 AED 544
AED 1,062 total
includes taxes & fees
27 Sep - 28 Sep
Center of Little Italy #1
1 bedroom, WiFi (free), bed sheets

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.
The price is AED 551
AED 784 total
includes taxes & fees
24 Sep - 25 Sep
Welcome to the Sandcastle Suite
Outdoor spa tub

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 AED 455
AED 794 total
includes taxes & fees
6 Oct - 7 Oct
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!
Interior

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

Embassy Suites by Hilton Cleveland Rockside

Embassy Suites by Hilton Cleveland Rockside

8/10 Good
"."
Hindy 1-night trip
Posted 4 hours ago
Embassy Suites by Hilton Cleveland Rockside

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.