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

Chesterland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Chesterland vacation rentals

Exterior

1. 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 AED 387
AED 589 total
includes taxes & fees
11 Aug - 12 Aug
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Interior

2. 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 AED 522
AED 1,208 total
includes taxes & fees
11 Aug - 12 Aug
Willow Woods Retreat - Farmhouse - Patio & Nature
TV

3. 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 AED 459
AED 569 total
includes taxes & fees
10 Aug - 11 Aug
1br-1bth- Furnished Apartment in Chardon
Cottage (4 Bedrooms) | Interior

4. 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 389
AED 893 total
includes taxes & fees
12 Aug - 13 Aug
Coastal Lake Erie Cottage w/ Amazing Water Views!
Outdoor dining

5. 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
10 Aug - 11 Aug
Cozy Country Apartment in Heart of Geauga County
Dining

6. Pine Lake Trout Club Cabin #8!!!

Pine Lake Trout Club Cabin #8!!!
Chagrin Falls
9.0 out of 10, Wonderful, (14 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
12 Aug - 13 Aug
Pine Lake Trout Club Cabin #8!!!
Dining

7. 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 AED 731
AED 1,388 total
includes taxes & fees
10 Aug - 11 Aug
Country Cottage Farm Stay at Stoneycreek Acres
TV, offices

8. 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 AED 279
AED 768 total
includes taxes & fees
31 Aug - 1 Sep
The Gallery House - Art curated by local artist!
Smart TV, fireplace, books

9. 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 AED 294
AED 633 total
includes taxes & fees
11 Aug - 12 Aug
Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
Interior

10. 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 AED 251
AED 946 total
includes taxes & fees
10 Aug - 11 Aug
Cleveland’s Legends' Lair | Themed | Sleeps 4
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, (84 reviews)
"I’ll recommend this place to anyone staying in the Cleveland area! Excellent communication and so much privacy (even with such close quarters!) thanks again!!"
United States
Rochelle
The price is AED 304
AED 650 total
includes taxes & fees
11 Aug - 12 Aug
Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch
Smart TV, fireplace, books

12. 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 AED 294
AED 650 total
includes taxes & fees
16 Aug - 17 Aug
Contemporary Coventry: 10% Off 2+Nights+Late Check Out
TV

13. 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 AED 405
AED 816 total
includes taxes & fees
1 Sep - 2 Sep
The House Hotels - Superior Road
Dining

14. Rest, Relax and Enjoy our Gentleman's Farm in Mantua

Rest, Relax and Enjoy our Gentleman's Farm in Mantua
Mantua
9.6 out of 10, Exceptional, (38 reviews)
"We had a great time here! The kitchen was well-stocked and we enjoyed the beautiful outdoor gardens! We would definitely come back again!"
United States
Dale D.
The price is AED 470
AED 959 total
includes taxes & fees
7 Sep - 8 Sep
Rest, Relax and Enjoy our Gentleman's Farm in Mantua
1 bedroom, WiFi (free), bed sheets

15. Welcome to the Sandcastle Suite

Welcome to the Sandcastle Suite
Fairport Harbor
9.8 out of 10, Exceptional, (36 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 799 total
includes taxes & fees
10 Aug - 11 Aug
Welcome to the Sandcastle Suite
Exterior

16. Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (97 reviews)
"Great location to enjoy some peaceful country living!"
United States
Jerry L.
The price is AED 569
AED 841 total
includes taxes & fees
10 Aug - 11 Aug
Little house on the farm
Coffee/tea maker, fridge, microwave, oven

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, (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 AED 441
AED 698 total
includes taxes & fees
2 Sep - 3 Sep
Large duplex king size bed and two queen size
1 bedroom, iron/ironing board, WiFi (free), bed sheets

18. 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 AED 397
AED 899 total
includes taxes & fees
1 Sep - 2 Sep
Modern Victorian Studio -Steps to Cleveland Clinic
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 AED 217
AED 567 total
includes taxes & fees
9 Sep - 10 Sep
Nice Apartment next to Christmas Story House
Dining

20. 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 AED 441
AED 911 total
includes taxes & fees
23 Aug - 24 Aug
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterland Hotel Reviews

Hampton Inn Cleveland-Downtown

Hampton Inn Cleveland-Downtown

10/10 Excellent
"Amazing"
Ingrid 2-night trip
Posted 2 hours ago
Hampton Inn Cleveland-Downtown

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.