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Chesterland Holiday Rentals

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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday Rentals in Chesterland

Fridge, microwave, oven, stovetop
Luxury Downtown Townhome w/ Private Garage Unit 16

Luxury Downtown Townhome w/ Private Garage Unit 16

2.0 star property
Downtown Cleveland
9.2 out of 10, Wonderful, (21)
"Location was great for a quick family weekend trip. "
United States
Crystal P.
The price is HK$350
HK$1,299 total
includes taxes & fees
23 Nov - 24 Nov
Luxury Downtown Townhome w/ Private Garage Unit 16
Smart TV
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, (47)
"I have stayed here before and enjoyed it just as much the second time. The place had a lot of charm, was very clean and was very convenient to where I was working. I will stay there again. "
United States
Kathryn
The price is HK$469
HK$857 total
includes taxes & fees
20 Nov - 21 Nov
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Exterior
Dwntwn Luxe Suite Rock Hall • Casino • Stadiums

Dwntwn Luxe Suite Rock Hall • Casino • Stadiums

2.0 star property
Downtown Cleveland
10.0 out of 10, Exceptional, (1)
"Clean, comfortable and stunning view!"
United States
Wayne
The price is HK$597
HK$1,258 total
includes taxes & fees
20 Nov - 21 Nov
Dwntwn Luxe Suite Rock Hall • Casino • Stadiums
1 bedroom, iron/ironing board, WiFi, bed sheets
Charming studio apartment in fantastic Cleveland Tremont area

Charming studio apartment in fantastic Cleveland Tremont area

2.0 star property
Tremont
10.0 out of 10, Exceptional, (3)
"it was beautiful apartment, very clean, host Derrick was very helpful, he responded to our text messages immediately. "
United States
Savitha C.
The price is HK$343
HK$879 total
includes taxes & fees
20 Nov - 21 Nov
Charming studio apartment in fantastic Cleveland Tremont area
TV
Nice Apartment next to Christmas Story House

Nice Apartment next to Christmas Story House

Tremont
9.8 out of 10, Exceptional, (24)
"Nice place to stay. Convenience within a 15-20 minute drive for sight seeing. Christmas house, museum and gift shop are right there. Even with that it is very quiet."
United States
Yvonna
The price is HK$389
HK$1,046 total
includes taxes & fees
20 Nov - 21 Nov
Nice Apartment next to Christmas Story House
Fridge, microwave, oven, stovetop
Luxury Downtown Townhome w/ Private Garage Unit 14

Luxury Downtown Townhome w/ Private Garage Unit 14

Downtown Cleveland
9.4 out of 10, Exceptional, (36)
"Good location, walkable to sports. "
United States
Michael C.
The price is HK$389
HK$1,342 total
includes taxes & fees
1 Dec - 2 Dec
Luxury Downtown Townhome w/ Private Garage Unit 14
Exterior detail
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Buckeye-Shaker
9.8 out of 10, Exceptional, (55)
"We had made a prior request that housekeeping avoid scented cleaning products as much as possible (due to allergies and sensitivities of people in our group). We were very pleased with their efforts, and our stay was allergy-free! Also, the host, Ken Love, was very responsive when I had questions/comments during and after our stay."
United States
Patricia
The price is HK$560
HK$1,238 total
includes taxes & fees
23 Nov - 24 Nov
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!
Outdoor dining
Crisp 2 bedroom upstairs apartment in historic duplex

Crisp 2 bedroom upstairs apartment in historic duplex

Stockyards
10.0 out of 10, Exceptional, (45)
"Had a great stay here while in Cleveland for a concert. Clean, comfortable, and great location. Would definitely stay again if in the area! "
United States
Ashley F.
The price is HK$762
HK$1,173 total
includes taxes & fees
20 Nov - 21 Nov
Crisp 2 bedroom upstairs apartment in historic duplex
Fridge, microwave, oven, stovetop
Luxe Flat w/ Heated Pool & Sauna • Gym•Heart of DT

Luxe Flat w/ Heated Pool & Sauna • Gym•Heart of DT

Downtown Cleveland
10.0 out of 10, Exceptional, (2)
"This place was so beautiful and comfortable!! My boyfriend and I loved. The location was great, parking was not. None of the garages was open to park in. We would have to constantly drive around to find on street parking. But the place itself was more than I imagined. Although parking was horrible I would still stay here again. Perfect location, quiet building, comfortable bed"
United States
Tierra U.
The price is HK$210
HK$1,223 total
includes taxes & fees
20 Nov - 21 Nov
Luxe Flat w/ Heated Pool & Sauna • Gym•Heart of DT
Fridge, microwave, oven, stovetop
Victorian Studio Steps from Cleveland Clinic

Victorian Studio Steps from Cleveland Clinic

Hough
10.0 out of 10, Exceptional, (1)
The price is HK$697
HK$1,708 total
includes taxes & fees
1 Dec - 2 Dec
Victorian Studio Steps from Cleveland Clinic
Fridge, microwave, oven, stovetop
Luxury Downtown Townhome w/ Private Garage Unit 7

Luxury Downtown Townhome w/ Private Garage Unit 7

Downtown Cleveland
9.6 out of 10, Exceptional, (17)
"This place was perfect for our stay and the garage made it so nice!"
United States
Amber D.
The price is HK$350
HK$1,299 total
includes taxes & fees
24 Nov - 25 Nov
Luxury Downtown Townhome w/ Private Garage Unit 7
Fridge, microwave, oven, stovetop
Historic Haven Hideaway California King Bed

Historic Haven Hideaway California King Bed

Ohio City
9.8 out of 10, Exceptional, (29)
"We had a blast here with our young children! We played Nintendo and pool and ping pong and hide and seek and everything was perfect!"
United States
Jillian M.
The price is HK$525
HK$1,648 total
includes taxes & fees
1 Dec - 2 Dec
Historic Haven Hideaway California King Bed
Fridge, microwave, oven, stovetop
Center of Little Italy #2

Center of Little Italy #2

University Circle
9.8 out of 10, Exceptional, (7)
" Nice apartment in a good location."
United States
Daniel
The price is HK$571
HK$1,417 total
includes taxes & fees
23 Nov - 24 Nov
Center of Little Italy #2
Fridge, microwave, oven, stovetop
Stylish Ohio City Retreat - Walk to West Side Market and Breweries

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

Ohio City
9.8 out of 10, Exceptional, (19)
"I had no complaints about our stay whatsoever. It was a very nice place."
United States
nick f.
The price is HK$583
HK$1,299 total
includes taxes & fees
23 Nov - 24 Nov
Stylish Ohio City Retreat - Walk to West Side Market and Breweries
Fridge, microwave, oven, stovetop
Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed

Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed

University Circle
9.6 out of 10, Exceptional, (13)
"Hosts were super responsive and helpful all along the way. Great stay."
United States
Laurel H.
The price is HK$487
HK$1,683 total
includes taxes & fees
1 Dec - 2 Dec
Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed
Interior
Coastal Lake Erie Cottage w/ Amazing Water Views!

Coastal Lake Erie Cottage w/ Amazing Water Views!

3.0 star property
Euclid
The price is HK$754
HK$1,392 total
includes taxes & fees
23 Nov - 24 Nov
Coastal Lake Erie Cottage w/ Amazing Water Views!
Fridge, microwave, oven, stovetop
Casual CLE: Relaxed Stay w/ Late Check Out

Casual CLE: Relaxed Stay w/ Late Check Out

Tremont
9.0 out of 10, Wonderful, (9)
"Great little comfortable spot. Host was very responsive and helpful. Highly recommend. "
United States
Erin
The price is HK$622
HK$1,399 total
includes taxes & fees
20 Nov - 21 Nov
Casual CLE: Relaxed Stay w/ Late Check Out
Property grounds
Residential Apartment w/Drumkit

Residential Apartment w/Drumkit

Willowick
10.0 out of 10, Exceptional, (18)
"Very clean and host was attentive."
United States
Amanda
The price is HK$731
HK$1,257 total
includes taxes & fees
20 Nov - 21 Nov
Residential Apartment w/Drumkit
Property grounds
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)
"Extremely helpful and accommodating. "
United States
Nancy M.
The price is HK$972
HK$1,912 total
includes taxes & fees
20 Nov - 21 Nov
Rest, Relax and Enjoy our Gentleman's Farm in Mantua
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
"Such a great hotel! Not only did they feed you for breakfast but they feed you for dinner too. The food was probably the best hotel food I've ever eaten. The staff was amazing and the rooms are spacious and comfortable. "
anthony 2-night trip
Posted 22 hours ago
Drury Plaza Hotel Cleveland Downtown

Find out more about Chesterland

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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 holiday rentals in Chesterland?

Yes, there are holiday rentals close to the most popular sights in Chesterland, or you can select a more secluded option if you're looking for a relaxing stay. Chesterland is known for its golf courses and ski areas.

What are some of the best holiday rentals that Chesterland has to offer?

Luxury Downtown Townhome w/ Private Garage Unit 13: This holiday home rental outside of 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 Alpine Valley are other places to visit while you're in town.

What are holiday rentals like in Chesterland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterland. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a small group gathering.