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Chesterland Vacation Rentals

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Sep 25 - Sep 26
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Sep 26 - Sep 27
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Sep 26 - Sep 28
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Oct 3 - Oct 5

Vacation Rentals in Chesterland

2125 Superior Living
Interior

2125 Superior Living

2.0 star property
6.2 out of 10, (45)
"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
City Apartment, City View | Private kitchen | Full-size fridge, microwave, stovetop, coffee/tea maker

Sleek DT Cleveland Apt at City Club

3.0 star property
9.4 out of 10, Exceptional, (100)
"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, (49)
"Great place "
The price is ￥13,152
￥17,580 total
includes taxes & fees
Sep 29 - Sep 30
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 ￥5,209
￥23,253 total
includes taxes & fees
Sep 28 - Sep 29
Luxury Downtown Townhome w/ Private Garage Unit 13
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, (29)
"I loved the stay it was very relaxing and it was in a great location "
The price is ￥14,023
￥29,522 total
includes taxes & fees
Sep 29 - Sep 30
Timeless Tremont-2 Bdrm near Downtown Cle
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 ￥4,428
￥7,380 total
includes taxes & fees
Oct 7 - Oct 8
The Farm at Grand River
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 ￥18,304
￥31,022 total
includes taxes & fees
Sep 29 - Sep 30
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!
Downtown King Loft | Free Parking
Fridge, microwave, oven, stovetop

Downtown King Loft | Free Parking

9.4 out of 10, Exceptional, (49)
"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 ￥8,488
￥26,179 total
includes taxes & fees
Sep 28 - Sep 29
Downtown King Loft | Free Parking
Quaint 2BR in Historical Little Italy
Smart TV

Quaint 2BR in Historical Little Italy

2.0 star property
8.8 out of 10, Excellent, (13)
"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 ￥13,949
￥22,806 total
includes taxes & fees
Sep 28 - Sep 29
Quaint 2BR in Historical Little Italy
Private 2 Level Apartment with Hot Tub in Tremont
Interior

Private 2 Level Apartment with Hot Tub in Tremont

9.4 out of 10, Exceptional, (29)
"Everything was great about the stay minus the parking situation, but there was always street parking to make it easier! "
The price is ￥18,466
￥25,847 total
includes taxes & fees
Sep 30 - Oct 1
Private 2 Level Apartment with Hot Tub in Tremont
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 ￥11,809
￥25,094 total
includes taxes & fees
Sep 29 - Sep 30
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 ￥996,368
￥1,118,589 total
includes taxes & fees
Sep 26 - Sep 27
Penthouse studio in the heart of downtown Cleveland
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 ￥25,374
￥50,468 total
includes taxes & fees
Sep 29 - Sep 30
Ohio City Home with Hot Tub Sleeps 8 + 2 more futons. Near Cleveland Attractions
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 ￥9,299
￥18,894 total
includes taxes & fees
Oct 3 - Oct 4
CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC
Stylish Ohio City Retreat - Walk to West Side Market and Breweries
Fridge, microwave, oven, stovetop

Stylish Ohio City Retreat - Walk to West Side Market and Breweries

9.8 out of 10, Exceptional, (16)
"Great place! The owner was very accommodating and answered any communication almost immediately."
The price is ￥11,013
￥24,709 total
includes taxes & fees
Sep 30 - Oct 1
Stylish Ohio City Retreat - Walk to West Side Market and Breweries
Hot Tub|Ping Pong|Sleeps 9|Retro Fun
Exterior

Hot Tub|Ping Pong|Sleeps 9|Retro Fun

10.0 out of 10, Exceptional, (18)
"The house was a great fit for me and my family. Very clean and comfortable. "
Hot Tub|Ping Pong|Sleeps 9|Retro Fun
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, (20)
"Bed were ok. Food options were great everything very close. Cleveland Clinic is also very close by. "
The price is ￥6,642
￥24,673 total
includes taxes & fees
Sep 29 - Sep 30
Luxury Downtown Townhome w/ Private Garage Unit 4
Charming 3-bedroom house with WiFi and AC in welcoming Cleveland
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi and AC in welcoming Cleveland

10.0 out of 10, Exceptional, (4)
"It was very nice and very spacious 10/10 "
The price is ￥21,994
￥38,888 total
includes taxes & fees
Sep 26 - Sep 27
Charming 3-bedroom house with WiFi and AC in welcoming Cleveland
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 ￥51,664
￥59,045 total
includes taxes & fees
Sep 26 - Sep 27
Lake front park near by -15 minutes east of downtown Cleveland
Simple, Chic 3-bedroom house in Cleveland Heights- Close to Cleveland Clinic
Property grounds

Simple, Chic 3-bedroom house in Cleveland Heights- Close to Cleveland Clinic

7.8 out of 10, Good, (10)
"I liked the neighborhood and the room inside the home."
Simple, Chic 3-bedroom house in Cleveland Heights- Close to 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

Drury Plaza Hotel Cleveland Downtown

Drury Plaza Hotel Cleveland Downtown

10/10 Excellent
"check-in and valet service was fast and friendly. hotel was clean. room was very comfortably. enjoyed our stay"
amy 2-night trip
Posted 1 day ago
Drury Plaza Hotel Cleveland Downtown

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:

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

Frequently asked questions

Are there vacation rentals in Chesterland?

Yes, you can find vacation rentals close to popular sights in Chesterland, or you can choose a more secluded option if you're looking for relaxation. Chesterland is known for its golf courses and ski areas.

What's the top vacation rental that Chesterland has to offer?

Luxury Downtown Townhome w/ Private Garage Unit 13: This vacation home rental near 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 Chester Town Hall are other places to visit while you're in town.

What are vacation rentals like in Chesterland?

Vacation rentals are private properties you can book for several days or longer in Chesterland. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family gatherings.