Photo by Kristin DePlatchett

Search Holiday Rentals in Chesterland

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Top Holiday Rentals in Chesterland

2125 Superior Living

2.0 star property
6.0 out of 10, (33)
"Loved the decor, vey clean, has everything you need. Very close to downtown, just a few bus stops away. "
2125 Superior Living

Sleek DT Cleveland Apt at City Club

3.0 star property
9.2 out of 10, Wonderful, (81)
"A beautifully designed space with lovely amenities and great, friendly staff that was willing to make accommodations. Would definitely recommend this property."
Sleek DT Cleveland Apt at City Club

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 £91
includes taxes & fees
14 Aug - 15 Aug
Crown royal presidential suite and fitness center

Luxury Downtown Townhome w/ Private Garage Unit 13

9.6 out of 10, Exceptional, (68)
"Very clean and convenient "
The price is £149
includes taxes & fees
17 Aug - 18 Aug
Luxury Downtown Townhome w/ Private Garage Unit 13

Lakefront Escape With Hot Tub & Modern Comforts

10.0 out of 10, Exceptional, (9)
"We enjoyed our time staying at this house! "
Lakefront Escape With Hot Tub & Modern Comforts

Simple, Chic 3-bedroom house in Cleveland Heights- Close to Cleveland Clinic

7.8 out of 10, Good, (10)
"I liked the neighborhood and the room inside the home."
Simple, Chic 3-bedroom house in Cleveland Heights- Close to Cleveland Clinic

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!

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

9.8 out of 10, Exceptional, (38)
"Great location, helpful and responsive host."
The price is £163
includes taxes & fees
8 Sept - 9 Sept
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!

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 £40
includes taxes & fees
14 Aug - 15 Aug
The Farm at Grand River

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

The price is £197
includes taxes & fees
14 Aug - 15 Aug
Charming 2-bedroom house with AC, WiFi in awesome Cleveland

Cozy Downtown Modern Condo in the Heart of it all

9.6 out of 10, Exceptional, (141)
"Had such a great time, so close to all the best attractions. Would stay again!"
The price is £104
includes taxes & fees
24 Aug - 25 Aug
Cozy Downtown Modern Condo in the Heart of it all

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 £606
includes taxes & fees
25 Aug - 26 Aug
Hot Tremont House - 6 Bed 3 Bath

Enormous Group Retreat - King Bed, Game Room, Private Yard, Near Downtown CLE!

8.6 out of 10, Excellent, (77)
"Enjoyed our stay.Only complaint, really, was that one of the bunk bedrooms only exit was through the master bedroom. Not a big deal.Home is old, it well kept. "
The price is £249
includes taxes & fees
2 Sept - 3 Sept
Enormous Group Retreat - King Bed, Game Room, Private Yard, Near Downtown CLE!

Beach View Suite #8

2.0 star property
9.0 out of 10, Wonderful, (2)
"Would recommend. We were in town for a 93rd birthday party and it was perfect for what we needed. Quick walk to beach, ice cream and diner. Provided all we needed"
The price is £136
includes taxes & fees
19 Aug - 20 Aug
Beach View Suite #8

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

10.0 out of 10, Exceptional, (63)
"Great stay! Felt like a home away from home!"
The price is £162
includes taxes & fees
14 Aug - 15 Aug
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!

Enjoy this historic charming spacious clean One-bedroom Apartment. Pet Friendly

6.2 out of 10, (21)
"Classic Cleveland Hts. apartment- spacious, solid. Had everything we needed and questions were answered promptly ~ Thanks! "
The price is £99
includes taxes & fees
18 Aug - 19 Aug
Enjoy this historic charming spacious clean One-bedroom Apartment. Pet Friendly

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

10.0 out of 10, Exceptional, (2)
"The manager did an amazing job at helping us find the place. Great accommodation and great service. A"
The price is £186
includes taxes & fees
19 Aug - 20 Aug
3 BR Home in South Cleveland w Easy Access to Cleveland Clinic, UH Hospitals, Hopkins Airport

Luxurious 3-BR Lakefront Cottage on Lake Erie - Book Your Lakeside Retreat Today

10.0 out of 10, Exceptional, (90)
"Wonderful place. Clean and peaceful. "
Luxurious 3-BR Lakefront Cottage on Lake Erie - Book Your Lakeside Retreat Today

Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

9.8 out of 10, Exceptional, (48)
"We really enjoyed staying here . It was clean and the host was very nice to us . Close to hospital and close to restaurants . We will return . "
The price is £131
includes taxes & fees
1 Sept - 2 Sept
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Hot Tub|Ping Pong|Sleeps 9|Retro Fun

10.0 out of 10, Exceptional, (12)
"The house was a great fit for me and my family. Very clean and comfortable. "
Hot Tub|Ping Pong|Sleeps 9|Retro Fun
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Luxury Downtown Townhome w/ Private Garage Unit 13: This holiday home rental outside of Chesterland is equipped with a balcony, air conditioning and laundry facilities to help you feel comfortable during your stay. 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. Chester Town Hall 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.