Chesterland Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Chesterland vacation rentals

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, (4 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 ￥24,675
￥28,303 total
includes taxes & fees
May 11 - May 12
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
Outdoor spa tub

Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
Madison
9.4 out of 10, Exceptional, (6 reviews)
"Super clean and cozy cabin! I can’t wait to stay again! "
United States
Alyssa T.
The price is ￥27,987
￥31,772 total
includes taxes & fees
May 27 - May 28
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
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, (8 reviews)
"Yes everything was amazing besides the TV’s not being in all rooms for entertainment."
United States
Temetrius
The price is ￥9,536
￥30,170 total
includes taxes & fees
May 12 - May 13
The Gallery House - Art curated by local artist!
Exterior

Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (96 reviews)
"Wonderful hosts, made us feel right at home!"
United States
Lynn
The price is ￥24,230
￥35,641 total
includes taxes & fees
May 14 - May 15
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 ￥9,223
￥24,122 total
includes taxes & fees
May 19 - May 20
Next 2 Christmas Story House/Tremont/5min downtown
Interior

Charming studio apartment in fantastic Cleveland Tremont area

Charming studio apartment in fantastic Cleveland Tremont area
Tremont
8.8 out of 10, Excellent, (20 reviews)
"Place was nice and meet our expectations. Located in a more rough area, but overall we had a good experience staying here. "
United States
Luke T.
The price is ￥6,894
￥19,243 total
includes taxes & fees
May 13 - May 14
Charming studio apartment in fantastic Cleveland Tremont area
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, (73 reviews)
"Great location for a Cleveland visit. Host was responsive and helpful. Will definitely stay again."
United States
Kathleen R.
The price is ￥11,255
￥25,824 total
includes taxes & fees
May 12 - May 13
Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch
Exterior

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Burton
10.0 out of 10, Exceptional, (60 reviews)
"We loved this little place. "
United States
Rolanda R.
The price is ￥14,772
￥23,370 total
includes taxes & fees
May 10 - May 11
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Dining

Acadia Farms Carriage House

Acadia Farms Carriage House
Northfield
9.6 out of 10, Exceptional, (5 reviews)
"Clean room, beautiful grounds, well equipped kitchen, great location for dog walks! Perfect for our family of four!"
United States
Natalie
The price is ￥18,217
￥31,308 total
includes taxes & fees
May 11 - May 12
Acadia Farms Carriage House
Exterior

Walk to Dining, Bars & Transit!

Walk to Dining, Bars & Transit!
Union-Miles Park
8.4 out of 10, Very Good, (144 reviews)
"It was very cozy. The host was very responsive for any issues we had. It was a very nice place to stay. We would highly recommend it. Love the location."
United States
dave f.
The price is ￥11,671
￥36,741 total
includes taxes & fees
May 11 - May 12
Walk to Dining, Bars & Transit!
Property grounds

Residential Apartment w/Drumkit

Residential Apartment w/Drumkit
Willowick
10.0 out of 10, Exceptional, (18 reviews)
"Great, quiet place! "
United States
Ranae K.
The price is ￥15,476
￥26,098 total
includes taxes & fees
Jun 7 - Jun 8
Residential Apartment w/Drumkit
Dining

Comfy Updated Historic Gem Pets OK 3B Vibrant Area

Comfy Updated Historic Gem Pets OK 3B Vibrant Area
Painesville
9.8 out of 10, Exceptional, (73 reviews)
"This location was perfect for our stay while visiting with family during the Christmas season. The host was very responsive and helpful. This location definitely had a home away from home feeling as we felt a warm welcome upon entering the home. "
United States
Patrick T.
The price is ￥18,926
￥46,338 total
includes taxes & fees
May 11 - May 12
Comfy Updated Historic Gem Pets OK 3B Vibrant Area
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
9.0 out of 10, Wonderful, (17 reviews)
"Cozy little apartment."
United States
Christina
The price is ￥12,506
￥26,950 total
includes taxes & fees
May 13 - May 14
Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
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, (85 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 ￥11,255
￥24,886 total
includes taxes & fees
May 11 - May 12
Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!
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 ￥14,069
￥29,513 total
includes taxes & fees
May 8 - May 9
Peaceful private apartment in the charming Hiram countryside
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 ￥17,234
￥34,429 total
includes taxes & fees
May 12 - May 13
The House Hotels - Superior Road
Dining

Pine Lake Trout Club Cabin #8!!!

Pine Lake Trout Club Cabin #8!!!
Chagrin Falls
8.8 out of 10, Excellent, (12 reviews)
"I always love staying here! "
United States
Jade R.
The price is ￥26,574
￥30,169 total
includes taxes & fees
May 20 - May 21
Pine Lake Trout Club Cabin #8!!!
1 bedroom, iron/ironing board, free WiFi, bed sheets

Steps to Cleveland Clinic - Bright Studio

Steps to Cleveland Clinic - Bright Studio
Hough
10.0 out of 10, Exceptional, (2 reviews)
"host was very nice and attentive !"
United States
Trinity D.
The price is ￥13,287
￥33,551 total
includes taxes & fees
May 19 - May 20
Steps to Cleveland Clinic - Bright Studio
TV

Upscale Little Italy Two Bedroom w/ Private Drive

Upscale Little Italy Two Bedroom w/ Private Drive
University Circle
9.6 out of 10, Exceptional, (9 reviews)
"Great parking. Everything working as expected. "
United States
Johan
The price is ￥15,476
￥39,870 total
includes taxes & fees
May 13 - May 14
Upscale Little Italy Two Bedroom w/ Private Drive
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, (35 reviews)
"Great location and place to stay."
United States
Robert G.
Spacious Ohio City Oasis | Close to Breweries+WSM
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

Fidelity Hotel

Fidelity Hotel

10/10 Excellent
"Great staff!! And food and drinks were amazing"
Samantha Beatriz 1-night trip
Posted 1 hour ago
Fidelity Hotel

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 4: 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.