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Chesterland Holiday Rentals

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Holiday Rentals in Chesterland

2125 Superior Living
Interior

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
Private kitchen

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
Crown royal presidential suite and fitness center
Property grounds

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 HK$693
HK$927 total
includes taxes & fees
5 Oct - 6 Oct
Crown royal presidential suite and fitness center
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, (73)
"Conveniently located downtown close to bars and attractions "
The price is HK$467
HK$1,428 total
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!
Outdoor spa tub

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 HK$965
HK$1,635 total
includes taxes & fees
8 Oct - 9 Oct
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!
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$233
HK$389 total
includes taxes & fees
5 Oct - 6 Oct
The Farm at Grand River
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, (31)
"I loved the stay it was very relaxing and it was in a great location "
The price is HK$739
HK$1,595 total
includes taxes & fees
6 Oct - 7 Oct
Timeless Tremont-2 Bdrm near Downtown Cle
Quaint 2BR in Historical Little Italy
Smart TV

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 HK$735
HK$1,202 total
includes taxes & fees
5 Oct - 6 Oct
Quaint 2BR in Historical Little Italy
CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC
Exterior

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 HK$490
HK$996 total
includes taxes & fees
7 Oct - 8 Oct
CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!
Outdoor spa tub

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 HK$965
HK$1,674 total
includes taxes & fees
5 Oct - 6 Oct
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!
Hot Tub|Ping Pong|Sleeps 9|Retro Fun
Exterior

Hot Tub|Ping Pong|Sleeps 9|Retro Fun

10.0 out of 10, Exceptional, (18)
"Amazing, centrally located house that was accommodating for all in our party :-) "
The price is HK$1,956
HK$4,355 total
includes taxes & fees
14 Oct - 15 Oct
Hot Tub|Ping Pong|Sleeps 9|Retro Fun
Hot Tremont House - 6 Bed 3 Bath
Fridge, microwave, oven, stovetop

Hot Tremont House - 6 Bed 3 Bath

9.6 out of 10, Exceptional, (10)
"We had a great time during our stay. The house had everything we needed for the evening. "
The price is HK$2,679
HK$6,230 total
includes taxes & fees
6 Oct - 7 Oct
Hot Tremont House - 6 Bed 3 Bath
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, (21)
"Bed were ok. Food options were great everything very close. Cleveland Clinic is also very close by. "
The price is HK$467
HK$1,428 total
includes taxes & fees
13 Oct - 14 Oct
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, (11)
"Awesome place, very convenient and easy to navigate "
The price is HK$564
HK$1,578 total
includes taxes & fees
6 Oct - 7 Oct
Luxury Apartment | Downtown | Free Parking
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$623
HK$1,323 total
includes taxes & fees
6 Oct - 7 Oct
Casual CLE: 1 bdrm near Downtown Cle
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, (17)
"Ideal location, super clean, and easy check in check out process! Perfect for our mini getaway!"
The price is HK$350
HK$1,301 total
includes taxes & fees
5 Oct - 6 Oct
Luxury Downtown Townhome w/ Private Garage Unit 16
Ohio City Home with Hot Tub Sleeps 8 + 2 more futons. Near Cleveland Attractions
Outdoor spa tub

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

9.0 out of 10, Wonderful, (4)
"Overall process was excellent. Excellent communication. Excellent check in and out!!!"
The price is HK$1,338
HK$2,661 total
includes taxes & fees
6 Oct - 7 Oct
Ohio City Home with Hot Tub Sleeps 8 + 2 more futons. Near Cleveland Attractions
Cozy Victorian Studio Steps from Cleveland Clinic
Fridge, microwave, oven, stovetop

Cozy Victorian Studio Steps from Cleveland Clinic

10.0 out of 10, Exceptional, (1)
Cozy Victorian Studio Steps from Cleveland Clinic
Downtown King Loft | Free Parking
Fridge, microwave, oven, stovetop

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 HK$447
HK$1,372 total
includes taxes & fees
6 Oct - 7 Oct
Downtown King Loft | Free Parking
Cheerful Family Manor- Sleeps 25 w/hot tub and private pool in Amish Country
Smart TV, fireplace

Cheerful Family Manor- Sleeps 25 w/hot tub and private pool in Amish Country

9.8 out of 10, Exceptional, (26)
"We absolutely loved our time together here. The house was the perfect size for our family to be able to spread out while still being together! We are hoping to make this our yearly Christmas meetup spot for many years to come! "
Cheerful Family Manor- Sleeps 25 w/hot tub and private pool in Amish Country
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

Wyndham Independence

Wyndham Independence

10/10 Excellent
"appreciate for all good things"
Liping 1-night trip
Posted 3 days ago
Wyndham Independence

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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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.