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 SAR 1,183
SAR 1,810 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 SAR 1,258
SAR 1,892 total
includes taxes & fees
28 Sep - 29 Sep
The Thistle House off Chardon Square
Interior

3. 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 SAR 409
SAR 1,048 total
includes taxes & fees
4 Oct - 5 Oct
Willow Woods Retreat - Farmhouse - Patio & Nature
Dining

4. 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 713 total
includes taxes & fees
28 Sep - 29 Sep
Pine Lake Trout Club Cabin #8!!!
Exterior

5. 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 SAR 1,183
SAR 1,269 total
includes taxes & fees
28 Sep - 29 Sep
Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.
Exterior

6. 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 SAR 399
SAR 605 total
includes taxes & fees
29 Sep - 30 Sep
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Outdoor dining

7. 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 995 total
includes taxes & fees
28 Sep - 29 Sep
Cozy Country Apartment in Heart of Geauga County
Dining

8. 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
Interior

9. Great Group Getaway: Games Galore + Outdoor Oasis

Great Group Getaway: Games Galore + Outdoor Oasis
Painesville
9.6 out of 10, Exceptional, (24 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.
The price is SAR 1,111
SAR 2,921 total
includes taxes & fees
5 Oct - 6 Oct
Great Group Getaway: Games Galore + Outdoor Oasis
Cottage (4 Bedrooms) | Interior

10. 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 473
SAR 993 total
includes taxes & fees
12 Oct - 13 Oct
Coastal Lake Erie Cottage w/ Amazing Water Views!
Dining

11. Historic Cleveland Heights Carriage House!

Historic Cleveland Heights Carriage House!
Cleveland Heights
9.6 out of 10, Exceptional, (58 reviews)
"Close to the Clinic, easy to walk to shops and eateries and walk/run. Very communicative host and this is my second stay!"
United States
Mary A.
The price is SAR 676
SAR 1,390 total
includes taxes & fees
28 Sep - 29 Sep
Historic Cleveland Heights Carriage House!
Property grounds

12. 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 SAR 392
SAR 649 total
includes taxes & fees
28 Sep - 29 Sep
Residential Apartment w/Drumkit
Coffee/tea maker, fridge, microwave, oven

13. 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 SAR 451
SAR 713 total
includes taxes & fees
28 Sep - 29 Sep
Large duplex king size bed and two queen size
Exterior

14. Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (98 reviews)
"Great location to enjoy some peaceful country living!"
United States
Jerry L.
The price is SAR 582
SAR 826 total
includes taxes & fees
28 Sep - 29 Sep
Little house on the farm
Smart TV, fireplace, books

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

Contemporary Coventry: 10% Off 2+Nights+Late Check Out
Cleveland
8.8 out of 10, Excellent, (60 reviews)
"Location was perfect. "
United States
Brian S.
The price is SAR 300
SAR 657 total
includes taxes & fees
7 Oct - 8 Oct
Contemporary Coventry: 10% Off 2+Nights+Late Check Out
Dining

16. 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 367
SAR 817 total
includes taxes & fees
28 Sep - 29 Sep
Charming 3-Bedroom Pet-Friendly Home by Lake Erie
Interior

17. Family-friendly 5-Star Rated 19th Century Restored Mansion

Family-friendly 5-Star Rated 19th Century Restored Mansion
Painesville
10.0 out of 10, Exceptional, (36 reviews)
"Wonderful stay @ this location. House is a great option for large families and gatherings. We were very pleased with the overall experience."
United States
Gene T.
The price is SAR 2,249
SAR 3,400 total
includes taxes & fees
28 Sep - 29 Sep
Family-friendly 5-Star Rated 19th Century Restored Mansion
TV, offices

18. 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 285
SAR 773 total
includes taxes & fees
25 Oct - 26 Oct
The Gallery House - Art curated by local artist!
Smart TV, fireplace, books

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

Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
Cleveland Heights
9.0 out of 10, Wonderful, (27 reviews)
"Excellent walkable location. Good for one night in town for an event."
United States
Whitney
The price is SAR 263
SAR 609 total
includes taxes & fees
28 Sep - 29 Sep
Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
Outdoor spa tub

20. Lovely 2 Bedroom Unit with a Hot Tub

Lovely 2 Bedroom Unit with a Hot Tub
Tremont
9.6 out of 10, Exceptional, (91 reviews)
"it was great"
United States
Taleah A.
The price is SAR 537
SAR 768 total
includes taxes & fees
28 Sep - 29 Sep
Lovely 2 Bedroom Unit with a Hot Tub
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

Crowne Plaza Cleveland at Playhouse Square by IHG

Crowne Plaza Cleveland at Playhouse Square by IHG

8/10 Good
"Clean room and easy check in and check out."
Lisa 1-night trip
Posted 5 hours ago
Crowne Plaza Cleveland at Playhouse Square by IHG

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.