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Chesterland Holiday Rentals

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Holiday Rentals in Chesterland

Sleek DT Cleveland Apt at City Club

3.0 star property
9.4 out of 10, Exceptional, (73)
"Great place to stay! Was near everything, super quiet and clean. Loved our stay here! "
Sleek DT Cleveland Apt at City Club

2125 Superior Living

2.0 star property
5.8 out of 10, (31)
"It was very pretty and spacious."
2125 Superior Living

Lakefront Escape With Hot Tub & Modern Comforts

10.0 out of 10, Exceptional, (8)
"We enjoyed our time staying at this house! "
The price is AU$895
includes taxes & fees
8 Aug - 9 Aug
Lakefront Escape With Hot Tub & Modern Comforts

Crown royal presidential suite and fitness center

8.8 out of 10, Excellent, (46)
"I spent a couple of days there, basically everything is fine, despite the fact that initially there were problems with entering the house, this problem was solved (I think this is not constant and other visitors will not have this problem). The area is really quiet, there is also a small store near the house. The owner is quite friendly and responsive, everything was in the house, but he could not turn on the TV, I hope this problem will be solved and in the future no one will encounter this...
The price is AU$186
includes taxes & fees
31 July - 1 Aug
Crown royal presidential suite and fitness center

Beach View Suite #8

2.0 star property
The price is AU$279
includes taxes & fees
4 Aug - 5 Aug
Beach View Suite #8

Luxury Downtown Townhome w/ Private Garage Unit 13

9.6 out of 10, Exceptional, (65)
"Very clean and convenient "
The price is AU$285
includes taxes & fees
31 July - 1 Aug
Luxury Downtown Townhome w/ Private Garage Unit 13

Cozy Downtown Modern Condo in the Heart of it all

9.6 out of 10, Exceptional, (140)
"Had such a great time, so close to all the best attractions. Would stay again!"
The price is AU$213
includes taxes & fees
3 Aug - 4 Aug
Cozy Downtown Modern Condo in the Heart of it all

Timeless Tremont-2 Bdrm near Downtown Cle

2.0 star property
9.6 out of 10, Exceptional, (23)
"I loved the stay it was very relaxing and it was in a great location "
The price is AU$315
includes taxes & fees
18 Aug - 19 Aug
Timeless Tremont-2 Bdrm near Downtown Cle

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

10.0 out of 10, Exceptional, (62)
"Great stay! Felt like a home away from home!"
The price is AU$333
includes taxes & fees
31 July - 1 Aug
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!

Coastal Lake Erie Cottage w/ Amazing Water Views!

9.6 out of 10, Exceptional, (20)
"We loved this cottage looking right over Lake Erie. It was clean and in a tucked away lane off the main road. The owner was very kind, accomodating, and easy to communicate with."
Coastal Lake Erie Cottage w/ Amazing Water Views!

The Farm at Grand River

7.4 out of 10, Good, (3)
"Excellent spot to camp, very peaceful. We would definitely revisit if we are in the area again. Property manager(s) were very friendly and accommodating."
The price is AU$80
includes taxes & fees
1 Aug - 2 Aug
The Farm at Grand River

Charming 2-bedroom house with AC, WiFi in awesome Cleveland

The price is AU$395
includes taxes & fees
31 July - 1 Aug
Charming 2-bedroom house with AC, WiFi in awesome Cleveland

Hot Tremont House - 6 Bed 3 Bath

9.8 out of 10, Exceptional, (8)
"We had a great time during our stay. The house had everything we needed for the evening. "
The price is AU$1,100
includes taxes & fees
31 July - 1 Aug
Hot Tremont House - 6 Bed 3 Bath

CLE BNB Getaway ★ 15 Guests ★ Stunning Kitchen ★ Game Room ★ Big Fenced Yard

8.6 out of 10, Excellent, (77)
"Easy access and great location "
The price is AU$547
includes taxes & fees
19 Aug - 20 Aug
CLE BNB Getaway ★ 15 Guests ★ Stunning Kitchen ★ Game Room ★ Big Fenced Yard

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

10.0 out of 10, Exceptional, (37)
"Great location, helpful and responsive host."
The price is AU$334
includes taxes & fees
4 Aug - 5 Aug
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!

3 BR Home in South Cleveland w Easy Access to Cleveland Clinic, UH Hospitals, Hopkins Airport

10.0 out of 10, Exceptional, (1)
"The manager did an amazing job at helping us find the place. Great accommodation and great service. A"
The price is AU$353
includes taxes & fees
31 July - 1 Aug
3 BR Home in South Cleveland w Easy Access to Cleveland Clinic, UH Hospitals, Hopkins Airport

Downtown King Loft | Free Parking

9.6 out of 10, Exceptional, (45)
"It was a very nice place!! It was very convenient and loved the underground parking!!! Would definitely recommend!!!!!"
The price is AU$275
includes taxes & fees
4 Aug - 5 Aug
Downtown King Loft | Free Parking

Mid Century Guest House on Wooded Lot

10.0 out of 10, Exceptional, (50)
"This property is absolutely wonderful. Beautiful and quiet."
Mid Century Guest House on Wooded Lot

Forever spring cabin

10.0 out of 10, Exceptional, (218)
"Our second time here and as good as the first. Very quiet and cozy. Would recommend."
Forever spring cabin

Gordon Square Studio ~ 4 Mi to Downtown Cleveland!

3.0 star property
10.0 out of 10, Exceptional, (3)
"Lovely stay - comfortable studio, communicative host, great location, and easy parking. "
Gordon Square Studio ~ 4 Mi to Downtown Cleveland!
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

Frequently asked questions

Are there holiday rentals in Chesterland?

Yes, there are holiday rentals close to the most popular sights in Chesterland, or you can select a more secluded option if you're looking for a relaxing stay. Chesterland is known for its golf courses and ski areas.

What are some of the best holiday rentals that Chesterland has to offer?

Lakefront Escape With Hot Tub & Modern Comforts: This holiday home rental outside of Chesterland is located on a lake, and has a garden, 1 hot tub and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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. Fowler's Mill Golf Course and West Geauga Plaza are other places to visit while you're in town.

What are holiday rentals like in Chesterland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterland. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a small group gathering.