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Holiday Rentals in Chesterland

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Holiday Rentals in Chesterland

2125 Superior Living

2.0 star property
6.2 out of 10, (46)
"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
9.4 out of 10, Exceptional, (106)
"Very clean, great price great stay."
Sleek DT Cleveland Apt at City Club

Luxe Flat w/ Heated Pool & Sauna • Gym•Heart of DT

10.0 out of 10, Exceptional, (6)
"It was fantastic couldn’t of asked for a better stay."
The price is €167
includes taxes & fees
14 Oct - 15 Oct
Luxe Flat w/ Heated Pool & Sauna • Gym•Heart of DT

Crown royal presidential suite and fitness center

8.8 out of 10, Excellent, (50)
"This place was very clean and the host responded quickly to any questions we had. "
The price is €107
includes taxes & fees
12 Oct - 13 Oct
Crown royal presidential suite and fitness center

Luxury Downtown Townhome w/ Private Garage Unit 13

9.6 out of 10, Exceptional, (73)
"Conveniently located downtown close to bars and attractions "
The price is €153
includes taxes & fees
23 Oct - 24 Oct
Luxury Downtown Townhome w/ Private Garage Unit 13

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

9.8 out of 10, Exceptional, (43)
"Nice property close to lots of restaurants. Clean and comfortable. "
The price is €186
includes taxes & fees
13 Oct - 14 Oct
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!

Quaint 2BR in Historical Little Italy

2.0 star property
9.0 out of 10, Wonderful, (15)
"Nice location with easy access to everything in university circle. The host was incredibly responsive with any questions we had. We had a great stay!"
The price is €138
includes taxes & fees
12 Oct - 13 Oct
Quaint 2BR in Historical Little Italy

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 €47
includes taxes & fees
11 Oct - 12 Oct
The Farm at Grand River

Timeless Tremont-2 Bdrm near Downtown Cle

2.0 star property
9.4 out of 10, Exceptional, (31)
"Great property, great location!!! Would stay again "
The price is €176
includes taxes & fees
22 Oct - 23 Oct
Timeless Tremont-2 Bdrm near Downtown Cle

CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC

8.8 out of 10, Excellent, (39)
"Very nice place. Convenient to many things to do in Cleveland. "
The price is €115
includes taxes & fees
14 Oct - 15 Oct
CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC

Hot Tub|Ping Pong|Sleeps 9|Retro Fun

10.0 out of 10, Exceptional, (19)
"Amazing, centrally located house that was accommodating for all in our party :-) "
The price is €536
includes taxes & fees
14 Oct - 15 Oct
Hot Tub|Ping Pong|Sleeps 9|Retro Fun

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

10.0 out of 10, Exceptional, (68)
"We absolutely loved our stay. Location was perfect for us to take in the Feast and enjoy neighborhood, restaurants and shopping. Our host was incredible and even took the time to message me and let me know that I had left behind some perishable goodies in the refrigerator. We are in the area often and will most definitely stay here again."
The price is €190
includes taxes & fees
12 Oct - 13 Oct
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!

Luxury Downtown Townhome w/ Private Garage Unit 4

9.6 out of 10, Exceptional, (21)
"Bed were ok. Food options were great everything very close. Cleveland Clinic is also very close by. "
The price is €153
includes taxes & fees
20 Oct - 21 Oct
Luxury Downtown Townhome w/ Private Garage Unit 4

Luxury Apartment | Downtown | Free Parking

10.0 out of 10, Exceptional, (11)
"Awesome place, very convenient and easy to navigate "
The price is €218
includes taxes & fees
15 Oct - 16 Oct
Luxury Apartment | Downtown | Free Parking

Luxury Downtown Townhome w/ Private Garage Unit 16

2.0 star property
9.2 out of 10, Wonderful, (19)
"Ideal location, super clean, and easy check in check out process! Perfect for our mini getaway!"
The price is €153
includes taxes & fees
20 Oct - 21 Oct
Luxury Downtown Townhome w/ Private Garage Unit 16

Casual CLE: 1 bdrm near Downtown Cle

8.8 out of 10, Excellent, (8)
"Great little comfortable spot. Host was very responsive and helpful. Highly recommend. "
The price is €152
includes taxes & fees
9 Nov - 10 Nov
Casual CLE: 1 bdrm near Downtown Cle

Downtown King Loft | Free Parking

9.4 out of 10, Exceptional, (51)
"Nice apartment in a good location for downtown activities. Note that bedroom and bathroom are on the second floor of the unit. Parking is right for larger vehicles. "
The price is €168
includes taxes & fees
12 Oct - 13 Oct
Downtown King Loft | Free Parking

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

9.0 out of 10, Wonderful, (6)
The price is €304
includes taxes & fees
12 Oct - 13 Oct
Ohio City Home with Hot Tub Sleeps 8 + 2 more futons. Near Cleveland Attractions

Beach View Suite #8

2.0 star property
9.4 out of 10, Exceptional, (6)
"Very Clean. Close to lake. "
The price is €159
includes taxes & fees
20 Oct - 21 Oct
Beach View Suite #8

Cozy Victorian Studio Steps from Cleveland Clinic

10.0 out of 10, Exceptional, (1)
Cozy Victorian Studio Steps from Cleveland Clinic
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

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, apart-hotels, 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 favorite 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 depends 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 €47 per night. Entering your travel dates in the search wizard you might find 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?

Crown royal presidential suite and fitness center: This holiday home rental outside of Chesterland has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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 Chester Town Hall 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.