Photo by Kristin DePlatchett

Chesterland Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Chesterland

Sleek DT Cleveland Apt at City Club

3.0 star property
Downtown Cleveland
9.4 out of 10, Exceptional, (120)
"Great gym. Free coffee in lobby. Great location"
United States
Keith
Sleek DT Cleveland Apt at City Club

2125 Superior Living

2.0 star property
Downtown Cleveland
6.4 out of 10, (53)
"safe parking, the area is a little rough. "
United States
Richard
2125 Superior Living

Charming studio apartment in fantastic Cleveland Tremont area

2.0 star property
Tremont
10.0 out of 10, Exceptional, (3)
"it was beautiful apartment, very clean, host Derrick was very helpful, he responded to our text messages immediately. "
United States
Savitha C.
The price is AU$173
includes taxes & fees
23 Dec - 24 Dec
Charming studio apartment in fantastic Cleveland Tremont area

Crown royal presidential suite and fitness center

Broadway-Slavic Village
8.8 out of 10, Excellent, (51)
"This place was very clean and the host responded quickly to any questions we had. "
United States
Nicole
The price is AU$182
includes taxes & fees
7 Dec - 8 Dec
Crown royal presidential suite and fitness center

Luxury Downtown Townhome w/ Private Garage Unit 13

Downtown Cleveland
9.6 out of 10, Exceptional, (83)
"Great location, close to amenities, super clean and very easy to rent ... A+++"
United States
Stacy
The price is AU$255
includes taxes & fees
8 Dec - 9 Dec
Luxury Downtown Townhome w/ Private Garage Unit 13

Luxury Downtown Townhome w/ Private Garage Unit 4

Downtown Cleveland
9.8 out of 10, Exceptional, (28)
"Great place to stay"
United States
April T.
The price is AU$263
includes taxes & fees
14 Dec - 15 Dec
Luxury Downtown Townhome w/ Private Garage Unit 4

Timeless Tremont- Enjoy 15% off 5+ nights

2.0 star property
Tremont
9.4 out of 10, Exceptional, (35)
"Great property, great location!!! Would stay again "
United States
Lea J.
The price is AU$276
includes taxes & fees
8 Dec - 9 Dec
Timeless Tremont- Enjoy 15% off 5+ nights

Modern Industrial 1BR Loft in Downtown Cleveland NEW

2.0 star property
Downtown Cleveland
6.0 out of 10, (4)
"Great place! Was a little hard to find but I like the secret location of it! Bathroom super beautiful and hostess very easy to communicate with!"
United States
Shai H.
The price is AU$207
includes taxes & fees
9 Dec - 10 Dec
Modern Industrial 1BR Loft in Downtown Cleveland NEW

Ohio City Getaway W/ Hot Tub, Pool Table and more!

Ohio City
9.6 out of 10, Exceptional, (72)
"Very fun stay!"
United States
Rebecca B.
Ohio City Getaway W/ Hot Tub, Pool Table and more!

Luxury Apartment | Downtown | Free Parking

Downtown Cleveland
10.0 out of 10, Exceptional, (14)
"Awesome place, very convenient and easy to navigate "
United States
Kevin
The price is AU$327
includes taxes & fees
8 Dec - 9 Dec
Luxury Apartment | Downtown | Free Parking

Charming 2-bedroom apartment with AC, Free Parking in wonderful Cleveland

2.0 star property
Downtown Cleveland
10.0 out of 10, Exceptional, (2)
"Very Nice Central Location would stay again "
United States
Summer L.
The price is AU$272
includes taxes & fees
7 Dec - 8 Dec
Charming 2-bedroom apartment with AC, Free Parking in wonderful Cleveland

Tranquil 1-bedroom apartment Downtown City Living

2.0 star property
Downtown Cleveland
6.0 out of 10, (1)
"There is a club across the street and two doors down. Saturday night was little rough with people arguing and cops"
United States
Michael B.
The price is AU$176
includes taxes & fees
8 Dec - 9 Dec
Tranquil 1-bedroom apartment Downtown City Living

Luxury Downtown Townhome w/ Private Garage Unit 16

2.0 star property
Downtown Cleveland
9.2 out of 10, Wonderful, (23)
"Location was great for a quick family weekend trip. "
United States
Crystal P.
The price is AU$255
includes taxes & fees
8 Dec - 9 Dec
Luxury Downtown Townhome w/ Private Garage Unit 16

Exclusive Luxury Penthouse - Heart of Downtown Cleveland - Rare Find

Downtown Cleveland
10.0 out of 10, Exceptional, (32)
"Great place in a great location!"
United States
David S.
The price is AU$1,044
includes taxes & fees
5 Jan - 6 Jan 2026
Exclusive Luxury Penthouse - Heart of Downtown Cleveland - Rare Find

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

University Circle
10.0 out of 10, Exceptional, (72)
"Great indoor and outdoor space. A lot of fun to stay there and within walking distance of some good food. Would definitely stay there again and recommend."
United States
Lauren B.
The price is AU$330
includes taxes & fees
7 Dec - 8 Dec
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!

Nice Apartment next to Christmas Story House

Tremont
9.8 out of 10, Exceptional, (24)
"We absolutely loved this place ! "
United States
Celeste K.
The price is AU$206
includes taxes & fees
9 Dec - 10 Dec
Nice Apartment next to Christmas Story House

Quaint 2BR in Historical Little Italy

2.0 star property
University Circle
9.0 out of 10, Wonderful, (17)
"Great location in little Italy. The space was quiet and it was great for us!"
United States
Martha V.
The price is AU$236
includes taxes & fees
8 Dec - 9 Dec
Quaint 2BR in Historical Little Italy

Ohio City Home with Hot Tub Sleeps 8 + 2 more futons. Near Cleveland Attractions

Ohio City
8.4 out of 10, Very good, (8)
"Overall process was excellent. Excellent communication. Excellent check in and out!!!"
United States
Alex N.
The price is AU$521
includes taxes & fees
8 Dec - 9 Dec
Ohio City Home with Hot Tub Sleeps 8 + 2 more futons. Near Cleveland Attractions

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

University Circle
9.8 out of 10, Exceptional, (45)
"Nice property close to lots of restaurants. Clean and comfortable. "
United States
Thomas
The price is AU$321
includes taxes & fees
8 Dec - 9 Dec
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!

Luxury Downtown Townhome w/ Private Garage Unit 11

Downtown Cleveland
10.0 out of 10, Exceptional, (15)
"My family and I stayed there recently for a concert. Great place, clean, good location, excellent communication with the owner! Would definitely stay again!"
United States
Marla A.
The price is AU$263
includes taxes & fees
14 Dec - 15 Dec
Luxury Downtown Townhome w/ Private Garage Unit 11
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

Find out more about Chesterland

Everything you need to know about Chesterland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesterland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterland holiday rentals we have selected for you start as low as AU$173 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesterland rentals

At Expedia, we put the best Chesterland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesterland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 11: 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. Fowler's Mill Golf Course and Alpine Valley 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.