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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Chesterland vacation rentals

Interior

1. Willow Woods Retreat - Farmhouse - Patio & Nature

Willow Woods Retreat - Farmhouse - Patio & Nature
Kirtland
9.4 out of 10, Exceptional, (41 reviews)
"Very nice stay. "
United States
MichaelLarryBetty S.
The price is SAR 533
SAR 1,250 total
includes taxes & fees
19 Aug - 20 Aug
Willow Woods Retreat - Farmhouse - Patio & Nature
Exterior

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, (64 reviews)
"Wonderful stay. It was clean, nice area, nice view, fun decor. Bed was comfortable. Good privacy."
United States
O'Neill
The price is SAR 412
SAR 619 total
includes taxes & fees
18 Aug - 19 Aug
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Cottage (4 Bedrooms) | Interior

3. 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 SAR 398
SAR 913 total
includes taxes & fees
19 Aug - 20 Aug
Coastal Lake Erie Cottage w/ Amazing Water Views!
TV

4. 1br-1bth- Furnished Apartment in Chardon

1br-1bth- Furnished Apartment in Chardon
Chardon
9.6 out of 10, Exceptional, (14 reviews)
"The apartment was very nice and the hosts appointed it very well. It is a great place to stay!"
United States
Eric M.
The price is SAR 469
SAR 582 total
includes taxes & fees
13 Aug - 14 Aug
1br-1bth- Furnished Apartment in Chardon
Smart TV, fireplace, books

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

Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
Cleveland Heights
8.8 out of 10, Excellent, (21 reviews)
"Great place to stay as we visit our daughter in Cleveland."
United States
Stephanie R.
The price is SAR 300
SAR 647 total
includes taxes & fees
13 Aug - 14 Aug
Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
Dining

6. 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 SAR 638
SAR 732 total
includes taxes & fees
14 Aug - 15 Aug
Pine Lake Trout Club Cabin #8!!!
Smart TV, fireplace, books

7. Contemporary Coventry: 10% Off 2+Nights+Late Check Out

Contemporary Coventry: 10% Off 2+Nights+Late Check Out
Cleveland
9.0 out of 10, Wonderful, (53 reviews)
"Location was perfect. "
United States
Brian S.
The price is SAR 300
SAR 665 total
includes taxes & fees
16 Aug - 17 Aug
Contemporary Coventry: 10% Off 2+Nights+Late Check Out
Dining

8. Country Cottage Farm Stay at Stoneycreek Acres

Country Cottage Farm Stay at Stoneycreek Acres
Newbury
10.0 out of 10, Exceptional, (75 reviews)
"Excellent communication with host and extremely clean, peaceful and beautiful place to stay "
United States
Jennifer T.
The price is SAR 747
SAR 1,419 total
includes taxes & fees
25 Aug - 26 Aug
Country Cottage Farm Stay at Stoneycreek Acres
TV, offices

9. 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.
The price is SAR 327
SAR 845 total
includes taxes & fees
31 Aug - 1 Sep
The Gallery House - Art curated by local artist!
Outdoor dining

10. 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 SAR 544
SAR 1,051 total
includes taxes & fees
20 Aug - 21 Aug
Cozy Country Apartment in Heart of Geauga County
Exterior detail

11. 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, (85 reviews)
"Another great stay!"
United States
Paul T.
The price is SAR 318
SAR 676 total
includes taxes & fees
24 Aug - 25 Aug
Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch
TV

12. The House Hotels - Superior Road

The House Hotels - Superior Road
Cleveland Heights
9.4 out of 10, Exceptional, (22 reviews)
"The house was great for a quick overnight stay and Billy was very responsive answering questions about the house and check-in process. The backyard was large and very accommodating for our two dogs. Would stay again!"
United States
Amy O.
The price is SAR 414
SAR 838 total
includes taxes & fees
1 Sep - 2 Sep
The House Hotels - Superior Road
TV

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

Heart of Little Italy- Walk to CWRU & Cleveland Clinic -Free Parking
University Circle
9.0 out of 10, Wonderful, (9 reviews)
"Enjoyed the quiet neighborhood and its convenient location near several Cleveland Clinics. Apartment was clean, great shower, WiFi and room for the four of us. Will check availability on future clinic visits."
United States
RONALD
The price is SAR 372
SAR 770 total
includes taxes & fees
26 Aug - 27 Aug
Heart of Little Italy- Walk to CWRU & Cleveland Clinic -Free Parking
Dining

14. Classic Meets Contemporary I Minutes to Cle Clinic

Classic Meets Contemporary I Minutes to Cle Clinic
Cleveland Heights
9.8 out of 10, Exceptional, (11 reviews)
"House was very clean and cozy. Great location."
United States
Monica
The price is SAR 327
SAR 804 total
includes taxes & fees
2 Sep - 3 Sep
Classic Meets Contemporary I Minutes to Cle Clinic
Interior

15. 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.
The price is SAR 287
SAR 1,016 total
includes taxes & fees
2 Sep - 3 Sep
Cleveland’s Legends' Lair | Themed | Sleeps 4
Coffee/tea maker, fridge, microwave, oven

16. 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, (80 reviews)
"3 travelers in town for a concert at Huntington Field. The place was clean. In a very nice area. 25 minute uber ride to the venue. The place had everything we needed. We all had our own beds. Would definitely recommend"
Canada
aaron
The price is SAR 451
SAR 713 total
includes taxes & fees
18 Aug - 19 Aug
Large duplex king size bed and two queen size
City Apartment, Multiple Beds, City View | Living area | 50-inch Smart TV with digital channels, Netflix, Hulu

17. 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, (215 reviews)
"Property was very nice. Reasonably priced."
United States
Derek
The price is SAR 186
SAR 676 total
includes taxes & fees
13 Aug - 14 Aug
Sleek DT Cleveland Apt at City Club
Dining

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.
The price is SAR 430
SAR 918 total
includes taxes & fees
10 Sep - 11 Sep
Charming 3-Bedroom Pet-Friendly Home by Lake Erie
TV

19. Nice Apartment next to Christmas Story House

Nice Apartment next to Christmas Story House
Tremont
9.6 out of 10, Exceptional, (29 reviews)
"Location was close to our activities "
United States
Brenda R.
The price is SAR 222
SAR 579 total
includes taxes & fees
8 Sep - 9 Sep
Nice Apartment next to Christmas Story House
1 bedroom, iron/ironing board, WiFi (free), bed sheets

20. Modern Victorian Studio -Steps to Cleveland Clinic

Modern Victorian Studio -Steps to Cleveland Clinic
Hough
10.0 out of 10, Exceptional, (14 reviews)
"Property is perfect for anyone needing a place to stay during a visit to Cleveland Clinic"
United States
Rebecca H.
The price is SAR 398
SAR 932 total
includes taxes & fees
18 Aug - 19 Aug
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.
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Top Chesterland Hotel Reviews

Hyatt Regency Cleveland At The Arcade

Hyatt Regency Cleveland At The Arcade

10/10 Excellent
"Great trip. Room was clean and staff was super helpful."
Jay 1-night trip
Posted less than an hour ago
Hyatt Regency Cleveland At The Arcade

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?

Crisp 2 bedroom upstairs apartment in historic duplex: This vacation home rental near Chesterland is located on a lake and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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. Berkshire Hill Golf Course and Fowler's Mill 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.