Chesterland Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Chesterland holiday rentals

A grassy area with two Adirondack chairs and a fire pit, overlooking a body of water.

1. 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 AU$354
includes taxes & fees
10 Nov - 11 Nov
Coastal Lake Erie Cottage w/ Amazing Water Views!
Living area

2. Sleek DT Cleveland Apt at City Club

Sleek DT Cleveland Apt at City Club
3.0 star property
Downtown Cleveland
9.2 out of 10, Wonderful, (263 reviews)
"Enjoyed our stay, right downtown and accessible to everything."
United States
Sean
The price is AU$356
includes taxes & fees
9 Nov - 10 Nov
Sleek DT Cleveland Apt at City Club
A modern kitchen with stainless steel appliances, wooden cabinets, a large island with a sink, and a view through a window.

3. ROVE LIVING/KB - Baricelli

ROVE LIVING/KB - Baricelli
4.0 star property
University Circle
8.0 out of 10, Very good, (3 reviews)
"The check-in is a bit tedious but necessary. The unit was spotless and well appointed. it is very convenient to Case Western Reserve University, University Hospitals, and Little Italy. There is a great dive bar across the street and the Murray Hill Market is a few blocks down Murray Hill Rd. Needless to say there are a lot Italian Restaurants within a short walk. One other thing, it is a very quiet neighborhood, which I was not expecting."
United States
Pete
The price is AU$284
includes taxes & fees
11 Nov - 12 Nov
ROVE LIVING/KB - Baricelli
A compact kitchen with modern appliances, a dining area with a table and chairs, and a sofa in a hallway.

4. Hilliard Lofts

Hilliard Lofts
2.0 star property
Downtown Cleveland
8.6 out of 10, Excellent, (4 reviews)
"Clean, comfortable loft apartment, walking distance to downtown, easy check in/check out."
United States
Craig
The price is AU$356
includes taxes & fees
9 Nov - 10 Nov
Hilliard Lofts
A bedroom with a bed, a dresser, a nightstand, a lamp, a window, and a ceiling fan.

5. 6 Mi to Dtwn! Historic Haven in Cleveland

6 Mi to Dtwn! Historic Haven in Cleveland
3.5 star property
Brooklyn Centre
The price is AU$663
includes taxes & fees
20 Nov - 21 Nov
6 Mi to Dtwn! Historic Haven in 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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Find holiday rentals that suit your style

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Cabins
Cabins
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Aparthotels
Aparthotels

Top Chesterland Hotel Reviews

A modern lobby with a sectional sofa, ottomans, and a reception desk.
Drury Inn & Suites Cleveland Beachwood

Drury Inn & Suites Cleveland Beachwood

Drury Inn & Suites Cleveland Beachwood
Orange

8/10 Good

It was fine for the one night stay we had en route to our destination. Breakfast was decent.
Australia
Nitika
Reviewed August 18, 2025
Drury Inn & Suites Cleveland Beachwood

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$283 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?

Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch: This holiday home rental outside of 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 holiday with amenities such as 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 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.