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Chesterland Holiday Rentals

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Check prices for these dates

Tonight
8 Sept - 9 Sept
Tomorrow
9 Sept - 10 Sept
This weekend
12 Sept - 14 Sept
Next weekend
19 Sept - 21 Sept

Holiday Rentals in Chesterland

Our top choices for Chesterland holiday rentals

2125 Superior Living
Interior

2125 Superior Living

2.0 star property
6.2 out of 10, (43)
"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
Private kitchen

Sleek DT Cleveland Apt at City Club

3.0 star property
9.4 out of 10, Exceptional, (94)
"Very clean, great price great stay."
Sleek DT Cleveland Apt at City Club
Cozy Downtown Modern Condo in the Heart of it all
Fridge, microwave, oven, stovetop

Cozy Downtown Modern Condo in the Heart of it all

9.6 out of 10, Exceptional, (148)
"Had such a great time, so close to all the best attractions. Would stay again!"
The price is HK$519
HK$1,065 total
includes taxes & fees
14 Sept - 15 Sept
Cozy Downtown Modern Condo in the Heart of it all
Crown royal presidential suite and fitness center
Property grounds

Crown royal presidential suite and fitness center

8.8 out of 10, Excellent, (49)
"It is very quaint. It felt like visiting a family. Very true to the advertisement. "
The price is HK$695
HK$929 total
includes taxes & fees
9 Sept - 10 Sept
Crown royal presidential suite and fitness center
Timeless Tremont-2 Bdrm near Downtown Cle
Fridge, microwave, oven, stovetop

Timeless Tremont-2 Bdrm near Downtown Cle

2.0 star property
9.4 out of 10, Exceptional, (27)
"I loved the stay it was very relaxing and it was in a great location "
The price is HK$741
HK$1,599 total
includes taxes & fees
24 Sept - 25 Sept
Timeless Tremont-2 Bdrm near Downtown Cle
Luxury Downtown Townhome w/ Private Garage Unit 13
Fridge, microwave, oven, stovetop

Luxury Downtown Townhome w/ Private Garage Unit 13

9.6 out of 10, Exceptional, (70)
"Good place to consider in future visits to Cleveland"
The price is HK$507
HK$1,489 total
includes taxes & fees
28 Sept - 29 Sept
Luxury Downtown Townhome w/ Private Garage Unit 13
The Farm at Grand River
Property grounds

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 HK$234
HK$390 total
includes taxes & fees
13 Sept - 14 Sept
The Farm at Grand River
Blue Bayou 3 bedroom 2 bath in South Cleveland king bed up to 8 guests
Interior

Blue Bayou 3 bedroom 2 bath in South Cleveland king bed up to 8 guests

7.0 out of 10, Good, (4)
"Me and my family enjoyed ourselves, everything was clean ans set up well. Just wish the tv’s were bigger "
Blue Bayou 3 bedroom 2 bath in South Cleveland king bed up to 8 guests
Casual CLE: 1 bdrm near Downtown Cle
Fridge, microwave, oven, stovetop

Casual CLE: 1 bdrm near Downtown Cle

8.6 out of 10, Excellent, (7)
"Nice location, sweet space."
The price is HK$624
HK$1,326 total
includes taxes & fees
14 Sept - 15 Sept
Casual CLE: 1 bdrm near Downtown Cle
Penthouse studio in the heart of downtown Cleveland
Exterior

Penthouse studio in the heart of downtown Cleveland

The price is HK$52,634
HK$60,027 total
includes taxes & fees
9 Sept - 10 Sept
Penthouse studio in the heart of downtown Cleveland
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!
Outdoor spa tub

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

9.8 out of 10, Exceptional, (41)
"Amazing. Owner thought of everything to make it feel like home "
The price is HK$967
HK$1,639 total
includes taxes & fees
11 Sept - 12 Sept
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!
Garden-level 2BR Pet-friendly Near Downtown
Front of property

Garden-level 2BR Pet-friendly Near Downtown

3.0 star property
2.0 out of 10, (1)
Garden-level 2BR Pet-friendly Near Downtown
Luxury Downtown Townhome w/ Private Garage Unit 4
Fridge, microwave, oven, stovetop

Luxury Downtown Townhome w/ Private Garage Unit 4

9.6 out of 10, Exceptional, (18)
"Bed were ok. Food options were great everything very close. Cleveland Clinic is also very close by. "
The price is HK$507
HK$1,473 total
includes taxes & fees
14 Sept - 15 Sept
Luxury Downtown Townhome w/ Private Garage Unit 4
Luxury Apartment | Downtown | Free Parking
Interior

Luxury Apartment | Downtown | Free Parking

10.0 out of 10, Exceptional, (8)
"Awesome place, very convenient and easy to navigate "
The price is HK$1,327
HK$2,522 total
includes taxes & fees
14 Sept - 15 Sept
Luxury Apartment | Downtown | Free Parking
Luxury Downtown Townhome w/ Private Garage Unit 11
Fridge, microwave, oven, stovetop

Luxury Downtown Townhome w/ Private Garage Unit 11

9.8 out of 10, Exceptional, (8)
"Very clean and bright, comfortable space!Walking distance to many fun places.Would recommend!"
The price is HK$507
HK$1,489 total
includes taxes & fees
28 Sept - 29 Sept
Luxury Downtown Townhome w/ Private Garage Unit 11
Downtown King Loft | Free Parking
Fridge, microwave, oven, stovetop

Downtown King Loft | Free Parking

9.6 out of 10, Exceptional, (47)
"Nice place to stay"
The price is HK$448
HK$1,375 total
includes taxes & fees
9 Sept - 10 Sept
Downtown King Loft | Free Parking
Lake front park near by -15 minutes east of downtown Cleveland
Exterior

Lake front park near by -15 minutes east of downtown Cleveland

The price is HK$2,729
HK$3,119 total
includes taxes & fees
9 Sept - 10 Sept
Lake front park near by -15 minutes east of downtown Cleveland
Quaint 2BR in Historical Little Italy
Smart TV

Quaint 2BR in Historical Little Italy

2.0 star property
8.8 out of 10, Excellent, (12)
"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 HK$737
HK$1,205 total
includes taxes & fees
14 Sept - 15 Sept
Quaint 2BR in Historical Little Italy
Luxury Downtown Townhome w/ Private Garage Unit 10
Fridge, microwave, oven, stovetop

Luxury Downtown Townhome w/ Private Garage Unit 10

9.2 out of 10, Wonderful, (7)
"This place was very clean and nice."
The price is HK$507
HK$1,473 total
includes taxes & fees
29 Sept - 30 Sept
Luxury Downtown Townhome w/ Private Garage Unit 10
Luxury Downtown Townhome w/ Private Garage Unit 16
Fridge, microwave, oven, stovetop

Luxury Downtown Townhome w/ Private Garage Unit 16

2.0 star property
9.2 out of 10, Wonderful, (15)
"Location was great for a quick family weekend trip. "
The price is HK$507
HK$1,489 total
includes taxes & fees
28 Sept - 29 Sept
Luxury Downtown Townhome w/ Private Garage Unit 16
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

Find out more about Chesterland

Search for holiday rentals in Chesterland on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterland using one of the methods below:

  • View our selection of featured holiday rentals in Chesterland
  • Use the map to find apartments and other holiday homes in the Chesterland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterland while they last

Look no further and take a look at our great range of rental properties in Chesterland!

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Explore a world of travel with Expedia

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. 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.