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

Our top choices for Chesterland vacation rentals

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, (189 reviews)
"Amazing place to stay! Location is amazing"
United States
Joseph
The price is AED 183
AED 850 total
includes taxes & fees
28 Jun - 29 Jun
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 AED 320
AED 823 total
includes taxes & fees
29 Jun - 30 Jun
The Gallery House - Art curated by local artist!
Interior

Charming studio apartment in fantastic Cleveland Tremont area

Charming studio apartment in fantastic Cleveland Tremont area
Tremont
8.2 out of 10, Very Good, (24 reviews)
"Enjoyed my stay host was great "
United States
Chrystlon L.
The price is AED 175
AED 465 total
includes taxes & fees
1 Jul - 2 Jul
Charming studio apartment in fantastic Cleveland Tremont area
Free WiFi, bed sheets

Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat

Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
Madison
9.6 out of 10, Exceptional, (5 reviews)
"This was an incredible stay for my wife and I. The cleanliness, quietness, and coziness was amazing. We will definitely be back for another anniversary stay. The multiple wineries around also help enhance the stay even more. You’re missing out if you don’t book this cabin. "
United States
Matthew
The price is AED 729
AED 821 total
includes taxes & fees
24 Jun - 25 Jun
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
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, (19 reviews)
"This place was very clean and nice."
United States
Jacqueline C.
The price is AED 165
AED 614 total
includes taxes & fees
24 Jun - 25 Jun
Luxury Downtown Townhome w/ Private Garage Unit 10
Smart TV, books

Stylish 2BR Ohio City Retreat: Near West Side Market, Breweries, & Downtown

Stylish 2BR Ohio City Retreat: Near West Side Market, Breweries, & Downtown
Ohio City
9.8 out of 10, Exceptional, (30 reviews)
"Great place to spend the weekend. "
United States
RaChel D.
The price is AED 338
AED 690 total
includes taxes & fees
29 Jun - 30 Jun
Stylish 2BR Ohio City Retreat: Near West Side Market, Breweries, & Downtown
Exterior detail

Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch

Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch
Buckeye-Shaker
9.8 out of 10, Exceptional, (80 reviews)
"Adequate on street parking."
United States
Linda
The price is AED 281
AED 625 total
includes taxes & fees
28 Jun - 29 Jun
Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch
TV

The House Hotels - Superior Road

The House Hotels - Superior Road
Cleveland Heights
9.4 out of 10, Exceptional, (21 reviews)
"A beautiful, comfortable, well kept apartment in a great location. This was ous second stay here so you know we like it!"
United States
Steve W.
The price is AED 463
AED 874 total
includes taxes & fees
6 Jul - 7 Jul
The House Hotels - Superior Road
Bathtub, hair dryer, towels, shampoo

Willow Woods Retreat - Farmhouse - Patio & Nature

Willow Woods Retreat - Farmhouse - Patio & Nature
Kirtland
9.4 out of 10, Exceptional, (38 reviews)
"Very nice stay. "
United States
MichaelLarryBetty S.
The price is AED 441
AED 1,109 total
includes taxes & fees
29 Jun - 30 Jun
Willow Woods Retreat - Farmhouse - Patio & Nature
Exterior detail

Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!

Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!
Buckeye-Shaker
9.4 out of 10, Exceptional, (88 reviews)
"The house is clean the host is always present whenever you needed I enjoyed my stay I can recommend you to book your stay"
United States
TULINAYO T.
The price is AED 235
AED 552 total
includes taxes & fees
24 Jun - 25 Jun
Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!
Fridge, microwave, oven, stovetop

Roof Top Townhouse in Tremont, Near Downtown!

Roof Top Townhouse in Tremont, Near Downtown!
Tremont
The price is AED 636
AED 1,121 total
includes taxes & fees
24 Jun - 25 Jun
Roof Top Townhouse in Tremont, Near Downtown!
Smart TV, offices

Modern Victorian Studio -Steps to Cleveland Clinic

Modern Victorian Studio -Steps to Cleveland Clinic
Hough
10.0 out of 10, Exceptional, (11 reviews)
"Property is perfect for anyone needing a place to stay during a visit to Cleveland Clinic"
United States
Rebecca H.
The price is AED 312
AED 777 total
includes taxes & fees
30 Jun - 1 Jul
Modern Victorian Studio -Steps to Cleveland Clinic
Exterior

Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (97 reviews)
"Absolutely perfect. Beautiful country home on a farm. Would 100% recommend and stay again. Amish store and restaurant just minutes away. Hosts left snacks and a variety of coffee and creamer choices. WiFi was great too as I had very little cell phone reception on the property. "
United States
Megan
The price is AED 569
AED 837 total
includes taxes & fees
24 Jun - 25 Jun
Little house on the farm
Dining

Next 2 Christmas Story House/Tremont/5min downtown

Next 2 Christmas Story House/Tremont/5min downtown
Tremont
9.4 out of 10, Exceptional, (95 reviews)
"Host was great"
United States
Jennifer E.
The price is AED 220
AED 571 total
includes taxes & fees
24 Jun - 25 Jun
Next 2 Christmas Story House/Tremont/5min downtown
Dining

Luxury Downtown Townhome w/ Private Garage Unit 14

Luxury Downtown Townhome w/ Private Garage Unit 14
Downtown Cleveland
9.4 out of 10, Exceptional, (45 reviews)
"Great location close enough to the Huntington Convention Center to walk there. Nice setup."
United States
Annette C.
The price is AED 220
AED 678 total
includes taxes & fees
9 Jul - 10 Jul
Luxury Downtown Townhome w/ Private Garage Unit 14
Shower, hair dryer, towels, soap

Center of Little Italy #1

Center of Little Italy #1
University Circle
9.6 out of 10, Exceptional, (18 reviews)
"Great stay and great location!"
United States
Katlyn A.
The price is AED 494
AED 957 total
includes taxes & fees
29 Jun - 30 Jun
Center of Little Italy #1
2 bedrooms, iron/ironing board, WiFi, bed sheets

Duck Island Getaway - Close to Downtown and West Side Market

Duck Island Getaway - Close to Downtown and West Side Market
Tremont
10.0 out of 10, Exceptional, (44 reviews)
"Everything was excellent. "
United States
Gary M.
The price is AED 452
AED 829 total
includes taxes & fees
29 Jun - 30 Jun
Duck Island Getaway - Close to Downtown and West Side Market
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 AED 331
AED 668 total
includes taxes & fees
13 Jul - 14 Jul
Eclectic Stay in Waterloo Arts District
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 AED 294
AED 633 total
includes taxes & fees
24 Jun - 25 Jun
Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
Living area

Cozy studio in delightful Cleveland with gym, parking and AC

Cozy studio in delightful Cleveland with gym, parking and AC
Downtown Cleveland
9.6 out of 10, Exceptional, (8 reviews)
"Really lovely place, looked just like the pictures "
United States
July
Cozy studio in delightful Cleveland with gym, parking and AC
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

Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

10/10 Excellent
"We always stay there! Never disappointed!"
wayne 1-night trip
Posted 2 hours ago
Holiday Inn Cleveland Clinic by IHG

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.