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Chesterland Vacation Rentals

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In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation 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)
"We use this property for business travel and it’s always worked out very well. The host is fantastic to work with. "
United States
Mark K.
$140 nightly
The price is $151
Nov 17 - Nov 18
Total with taxes and fees
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
$102 nightly
The price is $102
Nov 17 - Nov 18
Total with taxes and fees
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
$127 nightly
The price is $127
Nov 17 - Nov 18
Total with taxes and fees
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.
$113 nightly
The price is $113
Nov 26 - Nov 27
Total with taxes and fees
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)
"Didn’t spend a ton of time at the property because we were in town to hike at Cuyahoga National Park, but it was very clean and cozy! Spacious, updated, and conveniently located, too. Plenty of places in walking distance, and most popular destinations in the city are within 10-15 min drive! "
United States
Karina W.
$131 nightly
The price is $136
Nov 20 - Nov 21
Total with taxes and fees
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)
"Very clean and modern townhouse. "
United States
David G.
$140 nightly
The price is $151
Nov 17 - Nov 18
Total with taxes and fees
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, (54)
"We really enjoyed staying here . It was clean and the host was very nice to us . Close to hospital and close to restaurants . We will return . "
United States
Cheryl C.
$152 nightly
The price is $159
Nov 18 - Nov 19
Total with taxes and fees
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, (44)
"We had a wonderful stay. .It was close to all the activities we wanted to do and see. place was very clean and comfortable. If I ever need to come to Cleveland again, I would definitely stay again."
United States
Michelle G.
$143 nightly
The price is $151
Nov 17 - Nov 18
Total with taxes and fees
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.
$146 nightly
The price is $157
Nov 17 - Nov 18
Total with taxes and fees
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)
$201 nightly
The price is $218
Nov 17 - Nov 18
Total with taxes and fees
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)
"Clean with everything we needed. Conveniently located and easy to walk to the convention center and other places downtown. Perfect accommodations for attending a conference. "
United States
Renee C.
$155 nightly
The price is $167
Nov 19 - Nov 20
Total with taxes and fees
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)
"This was a cute apartment stocked with everything we needed for a great stay. The beds were unsupervised comfy and the main area was spacious. Check in was super easy. We could walk to the coffee shop and cool food options. There was a parking spot behind the apartment and free street parking on the side streets right next to the apartment."
United States
Khloe B.
$209 nightly
The price is $209
Nov 17 - Nov 18
Total with taxes and fees
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)
"We enjoyed our stay and the apartment was as presented in the listing. Easy walking distance to restaurants and to Cleveland Clinic. "
United States
Dan G.
$174 nightly
The price is $182
Nov 17 - Nov 18
Total with taxes and fees
Center of Little Italy #2
Fridge, microwave, oven, stovetop
Trendy in Tremont, Cleveland U

Trendy in Tremont, Cleveland U

Tremont
9.4 out of 10, Exceptional, (6)
"Kendall was very friendly and accommodating, the place was absolutely adorable. The only downside was that you had to park on the street, and there wasn’t anything available, but Kendall told us that since we were only staying one night, we could park in the driveway, which was very helpful. I would definitely stay here again."
United States
Kimberly
$173 nightly
The price is $188
Nov 17 - Nov 18
Total with taxes and fees
Trendy in Tremont, Cleveland U
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.
$159 nightly
The price is $166
Nov 18 - Nov 19
Total with taxes and fees
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)
"Very convenient location near CWRU. Nice property, lots of room and well maintained. Quiet neighborhood. Will stay again. "
United States
Dejan S.
$195 nightly
The price is $212
Nov 19 - Nov 20
Total with taxes and fees
Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed
Cottage (4 Bedrooms) | Interior
Coastal Lake Erie Cottage w/ Amazing Water Views!

Coastal Lake Erie Cottage w/ Amazing Water Views!

3.0 star property
Euclid
$170 nightly
The price is $179
Nov 17 - Nov 18
Total with taxes and fees
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)
"We stayed in town for a show at Rocket Mortgage Fieldhouse - the close proximity made it a seamless process to get Lyft and Uber services ! The place was a cozy spot for the night! Just watch that darn bench at the table, it’s a little off balance!"
United States
Amber D.
$180 nightly
The price is $180
Nov 20 - Nov 21
Total with taxes and fees
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)
"The owner put a lot of thought into ensuring that we were taken care of. We had everything we needed and more. The location was perfect "
United States
Matthew T.
$157 nightly
The price is $162
Nov 17 - Nov 18
Total with taxes and fees
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)
"This is our second stay at the farm which is now our new "go-to" when visiting family in the area. Excellent accommodations!"
United States
Nancy D.
$246 nightly
The price is $246
Nov 17 - Nov 18
Total with taxes and fees
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

The Westin Cleveland Downtown

The Westin Cleveland Downtown

10/10 Excellent
"Great view!! AWESOME STAY"
LaMar 1-night trip
Posted 10 hours ago
The Westin Cleveland Downtown

Find out more about Chesterland

Everything you need to know about Chesterland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesterland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $113 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesterland rentals

At Expedia, we put the best Chesterland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesterland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 13: 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 Alpine Valley 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.