Chesterland, Ohio, USA - 2-21-22: A small bridge in the Bessie Benner Metzenbaum Park

Chesterland Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Chesterland vacation rentals

Interior

Charming studio apartment in fantastic Cleveland Tremont area

Charming studio apartment in fantastic Cleveland Tremont area
Tremont
8.4 out of 10, Very Good, (25 reviews)
"Enjoyed my stay host was great "
United States
Chrystlon L.
The price is ￥7,425
￥20,205 total
includes taxes & fees
Jul 1 - Jul 2
Charming studio apartment in fantastic Cleveland Tremont area
City Apartment, Multiple Beds, City View | Living area | 50-inch Smart TV with digital channels, Netflix, Hulu

Sleek DT Cleveland Apt at City Club

Sleek DT Cleveland Apt at City Club
3.0 star property
Downtown Cleveland
9.4 out of 10, Exceptional, (190 reviews)
"Amazing place to stay! Location is amazing"
United States
Joseph
The price is ￥7,571
￥28,661 total
includes taxes & fees
Jun 28 - Jun 29
Sleek DT Cleveland Apt at City Club
TV, offices

The Gallery House - Art curated by local artist!

The Gallery House - Art curated by local artist!
Cleveland Heights
9.6 out of 10, Exceptional, (9 reviews)
"Everything was great. I will be back!"
United States
David T.
The price is ￥10,515
￥32,192 total
includes taxes & fees
Jun 29 - Jun 30
The Gallery House - Art curated by local artist!
Smart TV, fireplace, books

Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out

Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
Cleveland Heights
8.8 out of 10, Excellent, (20 reviews)
"I would definitely stay at this place again."
United States
catalina f.
The price is ￥12,924
￥27,851 total
includes taxes & fees
Jul 12 - Jul 13
Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
TV

Nice Apartment next to Christmas Story House

Nice Apartment next to Christmas Story House
Tremont
9.6 out of 10, Exceptional, (29 reviews)
"Location was close to our activities "
United States
Brenda R.
The price is ￥9,706
￥25,139 total
includes taxes & fees
Jun 30 - Jul 1
Nice Apartment next to Christmas Story House
1 bedroom, iron/ironing board, WiFi, bed sheets

Cozy studio near Cleve Clinic, Case

Cozy studio near Cleve Clinic, Case
Cleveland Heights
9.6 out of 10, Exceptional, (5 reviews)
"Very responsive host, nice and convenient area"
United States
Shannon
The price is ￥10,515
￥27,501 total
includes taxes & fees
Jul 13 - Jul 14
Cozy studio near Cleve Clinic, Case
TV

Heart of Little Italy- Walk to CWRU & Cleveland Clinic -Free Parking

Heart of Little Italy- Walk to CWRU & Cleveland Clinic -Free Parking
University Circle
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed the quiet neighborhood and its convenient location near several Cleveland Clinics. Apartment was clean, great shower, WiFi and room for the four of us. Will check availability on future clinic visits."
United States
RONALD
The price is ￥12,958
￥29,135 total
includes taxes & fees
Jul 20 - Jul 21
Heart of Little Italy- Walk to CWRU & Cleveland Clinic -Free Parking
Dining

Luxury Downtown Townhome w/ Private Garage Unit 10

Luxury Downtown Townhome w/ Private Garage Unit 10
Downtown Cleveland
9.2 out of 10, Wonderful, (21 reviews)
"This place was very clean and nice."
United States
Jacqueline C.
The price is ￥9,706
￥29,685 total
includes taxes & fees
Jul 13 - Jul 14
Luxury Downtown Townhome w/ Private Garage Unit 10
Interior

2-Story Downtown Townhome • FREE Parking • Gym

2-Story Downtown Townhome • FREE Parking • Gym
Downtown Cleveland
9.6 out of 10, Exceptional, (5 reviews)
"Really nice place. "
Canada
Peter
2-Story Downtown Townhome • FREE Parking • Gym
Private kitchen

Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside
Garrettsville
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful experience! The bed was very comfortable and the space was beautiful and clean. We enjoyed how quiet the area was and it was perfect for our weekend getaway. We will absolutely be staying here the next time we are out this way!"
United States
Ashley
The price is ￥14,540
￥30,824 total
includes taxes & fees
Jun 27 - Jun 28
Peaceful private apartment in the charming Hiram countryside
Smart TV, fireplace, books

Contemporary Coventry: 10% Off 2+Nights+Late Check Out

Contemporary Coventry: 10% Off 2+Nights+Late Check Out
Cleveland
9.0 out of 10, Wonderful, (51 reviews)
"Good place to stay"
United States
Matthew C.
The price is ￥12,924
￥28,271 total
includes taxes & fees
Jul 16 - Jul 17
Contemporary Coventry: 10% Off 2+Nights+Late Check Out
Interior

Eclectic Stay in Waterloo Arts District

Eclectic Stay in Waterloo Arts District
North Shore Collinwood
9.8 out of 10, Exceptional, (16 reviews)
"Very unique place! It was like sleeping in a gallery!"
United States
Leah
The price is ￥14,559
￥29,442 total
includes taxes & fees
Jul 13 - Jul 14
Eclectic Stay in Waterloo Arts District
Smart TV, fireplace

Cleveland Loft-Wolstein/Progressive/Playhouse/CSU.

Cleveland Loft-Wolstein/Progressive/Playhouse/CSU.
Downtown Cleveland
9.4 out of 10, Exceptional, (14 reviews)
"Was perfect for what we needed - walking distance to food, entertainment and Arena."
United States
Jerry B.
The price is ￥15,653
￥36,965 total
includes taxes & fees
Jul 14 - Jul 15
Cleveland Loft-Wolstein/Progressive/Playhouse/CSU.
Exterior detail

Luxury Downtown Townhome w/ Private Garage Unit 7

Luxury Downtown Townhome w/ Private Garage Unit 7
Downtown Cleveland
9.6 out of 10, Exceptional, (25 reviews)
"Short walk to the casino and the arena. Nice deli and brewery nearby. Quiet at night! "
United States
Zachary R.
The price is ￥9,706
￥29,846 total
includes taxes & fees
Jul 9 - Jul 10
Luxury Downtown Townhome w/ Private Garage Unit 7
Exterior

Dwntwn Suite, RnR, Casino, Stadiums, RnR Hof!

Dwntwn Suite, RnR, Casino, Stadiums, RnR Hof!
Downtown Cleveland
8.6 out of 10, Excellent, (10 reviews)
"Great location."
United States
Matthew
The price is ￥11,567
￥25,317 total
includes taxes & fees
Jun 28 - Jun 29
Dwntwn Suite, RnR, Casino, Stadiums, RnR Hof!
Interior

Quaint 2BR in Historical Little Italy

Quaint 2BR in Historical Little Italy
University Circle
9.0 out of 10, Wonderful, (23 reviews)
"Very Clean, Walking distance to alot of dinner options. Enjoyed our stay."
United States
John K.
The price is ￥16,986
￥26,692 total
includes taxes & fees
Jul 23 - Jul 24
Quaint 2BR in Historical Little Italy
Smart TV, books

Spacious Ohio City Oasis | Close to Breweries+WSM

Spacious Ohio City Oasis | Close to Breweries+WSM
Ohio City
10.0 out of 10, Exceptional, (36 reviews)
"Great location and place to stay."
United States
Robert G.
The price is ￥15,692
￥34,978 total
includes taxes & fees
Jun 29 - Jun 30
Spacious Ohio City Oasis | Close to Breweries+WSM
Beach nearby

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

CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC
Goodrich-Kirtland Park
8.8 out of 10, Excellent, (49 reviews)
"Nice place with no problems and a nice area. Would use to stay in Cleveland again."
United States
Austin
The price is ￥11,809
￥23,133 total
includes taxes & fees
Jul 13 - Jul 14
CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC
Smart TV, fireplace, foosball, table tennis

Chic 1-bed loft in Playhouse square, near Stadiums, Theater, Dining, Pets OK

Chic 1-bed loft in Playhouse square, near Stadiums, Theater, Dining, Pets OK
Downtown Cleveland
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful place "
United States
Corey J.
Chic 1-bed loft in Playhouse square, near Stadiums, Theater, Dining, Pets OK
1 bedroom, iron/ironing board, free WiFi, bed sheets

Steps to Cleveland Clinic - Bright Studio

Steps to Cleveland Clinic - Bright Studio
Hough
8.0 out of 10, Very Good, (3 reviews)
"host was very nice and attentive !"
United States
Trinity D.
The price is ￥13,750
￥34,235 total
includes taxes & fees
Jun 30 - Jul 1
Steps to Cleveland Clinic - Bright Studio
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

Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

10/10 Excellent
"Clean room and very helpful staff!"
Rowan 2-night trip
Posted less than an hour ago
Hilton Garden Inn Cleveland Downtown

Find out more about Chesterland

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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?

Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch: This vacation home rental near 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 vacation with amenities like a selection of games.

What can I see and do in Chesterland?

Chagrin River and Silo Picnic Area are a couple of lovely local spots to get outside and enjoy nature. Fowler's Mill Golf Course and West Geauga Plaza 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.