Chesterland Vacation Rentals

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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Chesterland vacation rentals

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)
"The host was fantastic with communication. The amenities were great"
United States
Sean E.
The price is ￥23,262
￥26,450 total
includes taxes & fees
Apr 27 - Apr 28
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
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 ￥23,262
￥26,450 total
includes taxes & fees
Apr 27 - Apr 28
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
Exterior

Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (95 reviews)
"Wonderful hosts, made us feel right at home!"
United States
Lynn
The price is ￥24,704
￥36,339 total
includes taxes & fees
Apr 29 - Apr 30
Little house on the farm
Outdoor dining

Beautiful cabin situated on wooded land with nice yard clearing and small stream

Beautiful cabin situated on wooded land with nice yard clearing and small stream
Madison
10.0 out of 10, Exceptional, (11 reviews)
"The location was very peaceful and relaxing. We felt at home with nature and enjoyed our time very much!"
United States
Steven B.
The price is ￥20,719
￥26,919 total
includes taxes & fees
May 1 - May 2
Beautiful cabin situated on wooded land with nice yard clearing and small stream
Beach nearby, sun loungers, beach towels

The View! Hot Tub-Golf Cart-Beaches-Billiards-King-Cottage Retreat Full of Fun

The View! Hot Tub-Golf Cart-Beaches-Billiards-King-Cottage Retreat Full of Fun
Fairport Harbor
10.0 out of 10, Exceptional, (60 reviews)
"Efficient booking, entry, and exit- The space was very clean and thoughtfully staged for a visit. We had a wonderful stay!"
United States
Kimberly P.
The price is ￥29,546
￥60,035 total
includes taxes & fees
Apr 26 - Apr 27
The View! Hot Tub-Golf Cart-Beaches-Billiards-King-Cottage Retreat Full of Fun
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 ￥17,249
￥43,620 total
includes taxes & fees
Apr 26 - Apr 27
Comfy Updated Historic Gem Pets OK 3B Vibrant 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 ￥11,475
￥26,329 total
includes taxes & fees
Apr 27 - Apr 28
Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch
Beach nearby, sun loungers, beach towels

Cozy Centrally Located Gem-King, Hot Tub, Pets OK, Shops & 15 Mins to Lake Erie

Cozy Centrally Located Gem-King, Hot Tub, Pets OK, Shops & 15 Mins to Lake Erie
Mentor
10.0 out of 10, Exceptional, (77 reviews)
"This was our second time staying here and we were again impressed with the details and luxury provided by the host. We will definitely be back!"
United States
Megan And Marty O.
The price is ￥20,719
￥48,802 total
includes taxes & fees
Apr 27 - Apr 28
Cozy Centrally Located Gem-King, Hot Tub, Pets OK, Shops & 15 Mins to Lake Erie
TV

The House Hotels - Superior Road

The House Hotels - Superior Road
Cleveland Heights
9.4 out of 10, Exceptional, (20 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 ￥17,572
￥34,307 total
includes taxes & fees
Apr 27 - Apr 28
The House Hotels - Superior Road
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 ￥18,408
￥31,318 total
includes taxes & fees
Apr 27 - Apr 28
Acadia Farms Carriage House
TV, offices

The Gallery House - Art curated by local artist!

The Gallery House - Art curated by local artist!
Cleveland Heights
9.8 out of 10, Exceptional, (7 reviews)
"Yes everything was amazing besides the TV’s not being in all rooms for entertainment."
United States
Temetrius
The price is ￥9,722
￥30,601 total
includes taxes & fees
Apr 26 - Apr 27
The Gallery House - Art curated by local artist!
Interior

Willow Woods Retreat - Farmhouse - Patio & Nature

Willow Woods Retreat - Farmhouse - Patio & Nature
Kirtland
9.4 out of 10, Exceptional, (36 reviews)
"Fantastic communication with the host and the most comfortable beds we have ever slept in! This home is charming and decorated elegantly with plenty of room for visiting. "
United States
Holly G.
The price is ￥17,408
￥46,475 total
includes taxes & fees
Apr 26 - Apr 27
Willow Woods Retreat - Farmhouse - Patio & Nature
TV

Nice Apartment next to Christmas Story House

Nice Apartment next to Christmas Story House
Tremont
9.8 out of 10, Exceptional, (27 reviews)
"Location was close to our activities "
United States
Brenda R.
The price is ￥9,403
￥24,594 total
includes taxes & fees
Apr 30 - May 1
Nice Apartment next to Christmas Story House
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 ￥11,475
￥25,373 total
includes taxes & fees
Apr 27 - Apr 28
Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!
Interior

Charming studio apartment in fantastic Cleveland Tremont area

Charming studio apartment in fantastic Cleveland Tremont area
Tremont
9.0 out of 10, Wonderful, (18 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 ￥8,033
￥20,624 total
includes taxes & fees
Apr 27 - Apr 28
Charming studio apartment in fantastic Cleveland Tremont area
Outdoor spa tub

Vineyard View | Walk to Wineries & River| Hot Tub

Vineyard View | Walk to Wineries & River| Hot Tub
Madison
10.0 out of 10, Exceptional, (66 reviews)
"Great amenities and beautiful setting"
United States
Joyce L.
The price is ￥46,742
￥76,143 total
includes taxes & fees
Apr 26 - Apr 27
Vineyard View | Walk to Wineries & River| Hot Tub
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, (59 reviews)
"We loved this little place. "
United States
Rolanda R.
The price is ￥16,066
￥24,832 total
includes taxes & fees
Apr 28 - Apr 29
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Dining

Rest, Relax and Enjoy our Gentleman's Farm in Mantua

Rest, Relax and Enjoy our Gentleman's Farm in Mantua
Mantua
9.6 out of 10, Exceptional, (38 reviews)
"We had a great time here! The kitchen was well-stocked and we enjoyed the beautiful outdoor gardens! We would definitely come back again!"
United States
Dale D.
The price is ￥20,401
￥41,439 total
includes taxes & fees
May 11 - May 12
Rest, Relax and Enjoy our Gentleman's Farm in Mantua
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 ￥14,990
￥25,780 total
includes taxes & fees
Apr 26 - Apr 27
Residential Apartment w/Drumkit
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 ￥14,344
￥30,410 total
includes taxes & fees
May 10 - May 11
Peaceful private apartment in the charming Hiram countryside
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 Cleveland Downtown

Hilton Cleveland Downtown

10/10 Excellent
"Great location . Friendly staff, Room was clean , comfy and had a great lake view. Would stay again . Highly recommend for staying in downtown area"
Lance 1-night trip
Posted 7 hours ago
Hilton Cleveland Downtown

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 11: 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. Chester Town Hall 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.