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Chesterland Vacation Rentals

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Vacation Rentals in Chesterland

Property grounds
LOCATION!- City Getaway in the FLATS!
10.0 out of 10, Exceptional, (11)
"The house is nice, roomy, and clean. Hot tub is fantastic!! The only bad thing is how noisy the street front bedroom is. Other then that house great! Close to everything. Would stay again."
LOCATION!- City Getaway in the FLATS!
Smart TV, fireplace, books, stereo
Mid Century Guest House on Wooded Lot
10.0 out of 10, Exceptional, (22)
"Our stay was perfect, our host Mary was so easy to communicate with and left us the best little Solar eclipse trove of Moon Pies and Sun Chips with a special boutique popcorn made for the solar eclipse event. The home was immaculately decorated in mid-century vibe, was extremely quiet, private and located close enough where we needed to be! Wonderful! 5 Stars across the board!"
Mid Century Guest House on Wooded Lot
Property grounds
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!
10.0 out of 10, Exceptional, (24)
"Absolutely the cutest place. Quiet, clean, and all the amenities. The hot tub area was quaint and well kept. Fun little getaway for a night. Will definitely be back! "
The price is CA $163
CA $290 total
includes taxes & fees
May 23 - May 24
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!
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Property grounds
Rated Top 4 Places to Stay in Cleveland by cleveland.com newspaper!
10.0 out of 10, Exceptional, (23)
"Plenty of room, plenty of comfort, and plenty products and items you need for your stay. A great spot if you're heading to downtown events but want to stay a bit away from the all the action."
The price is CA $408
CA $651 total
includes taxes & fees
May 22 - May 23
Rated Top 4 Places to Stay in Cleveland by cleveland.com newspaper!
Beach nearby, sun loungers, beach towels
RIVERFRONT Cottage-Hot Tub, Billiards, Golf Cart, Pet Friendly
10.0 out of 10, Exceptional, (22)
"Nice getaway, clean provided basic necessity as well, well though out."
RIVERFRONT Cottage-Hot Tub, Billiards, Golf Cart, Pet Friendly
Private kitchen
Ohio City Getaway! Sleeps 12, Games, Near Downtown
10.0 out of 10, Exceptional, (1)
"Overall great stay….would recommend to anyone who just wants to spend time with family together, neighbors were even nice doordash mistakenly put our order on the wrong porch & she kindly kept it for us and even helped walk it over it’s was a couple cases of waters. House was very nice & looked exactly how it’s pictured on the website."
Ohio City Getaway! Sleeps 12, Games, Near Downtown
Fridge, microwave, oven, stovetop
Cozy Downtown Modern Condo in the Heart of it all
9.8 out of 10, Exceptional, (87)
"The apartment was exactly as described, the property manager was quick to respond to questions I had. The location of the apartment is perfect for anyone attending a game or touring the hall of fame. We were close to the location we needed to be at every morning and we saved cash staying here instead of a hotel by cooking meals and making our own coffee."
The price is CA $129
CA $225 total
includes taxes & fees
May 22 - May 23
Cozy Downtown Modern Condo in the Heart of it all
Property grounds
Lovely 2 Bedroom Unit with a Hot Tub
9.8 out of 10, Exceptional, (30)
"maybe mention sbout thr smallish apartment size rooms But overall the place and area was fine ! Love the Cleveland Area"
The price is CA $177
CA $259 total
includes taxes & fees
May 23 - May 24
Lovely 2 Bedroom Unit with a Hot Tub
Exterior
Perfect! near Cleveland Clinic, CWRU, UH, Downtown & Sports venues w/Porch!
9.8 out of 10, Exceptional, (25)
"Needing to be spending several days doing to do tests at Cleveland Clinic, this was the first time we decided to do a Vrbo rather than a hotel. Perfectly located and quiet, even with the windows open at night. Ken was more than gracious, allowing us a later check out so we didn't have to sit at the clinic waiting for my appointment. We are so grateful!"
Perfect! near Cleveland Clinic, CWRU, UH, Downtown & Sports venues w/Porch!
Fridge, microwave, oven, stovetop
Downtown Sq: Stadium, Casino, Rock Hall, Clinic
9.8 out of 10, Exceptional, (6)
"It was amazing. We LOVED being right in the middle of everything!! The apt was perfect. Thanks you!"
The price is CA $90
CA $234 total
includes taxes & fees
May 22 - May 23
Downtown Sq: Stadium, Casino, Rock Hall, Clinic
Fridge, microwave, oven, stovetop
Ohio City Getaway W/ Hot Tub, Pool Table and more!
9.8 out of 10, Exceptional, (38)
"We enjoyed our visit. The house is well maintained and provides many entertainment options. Instructions were clear and the property was very close to attractions. Only a ten minute drive to downtown and 15 minutes to the Art Museum. Great ice cream shop nearby and having the west side market in the area was terrific. Would stay there again."
Ohio City Getaway W/ Hot Tub, Pool Table and more!
View from room
ROOST Cleveland
4.0 star property
9.6 out of 10, Exceptional, (222)
"Very clean and beautiful apartment. Near many restaurants and attractions. I would definitely recommend. "
The price is CA $271
CA $319 total
includes taxes & fees
May 29 - May 30
ROOST Cleveland
Balcony
1 Bed loft Condo Dntn Cleveland W 6th n st clair
9.6 out of 10, Exceptional, (17)
"Great communication "
The price is CA $94
CA $240 total
includes taxes & fees
May 22 - May 23
1 Bed loft Condo Dntn Cleveland W 6th n st clair
Private kitchen
Spacious Cozy Unit! 0.2mi from Progressive Field!
9.6 out of 10, Exceptional, (5)
"Nice spot, very convenient access to just about everything!"
Spacious Cozy Unit! 0.2mi from Progressive Field!
Smart TV, fireplace, books
Contemporary Coventry:1 bd w Fireplace. NEAR Case, Cle Clinic, UH, downtown!
9.4 out of 10, Exceptional, (16)
"So quaint and cute! Property manager was super communicative and my partner and I had a great time!"
The price is CA $125
CA $248 total
includes taxes & fees
May 27 - May 28
Contemporary Coventry:1 bd w Fireplace. NEAR Case, Cle Clinic, UH, downtown!
Fridge, microwave, oven, stovetop
Large duplex king size bed and two queen size
9.4 out of 10, Exceptional, (13)
"Nice and clean. Spacious. Kitchen well equipped, even had ground coffee. Place has character you'd expect from a century home, which for us added charm."
The price is CA $199
CA $290 total
includes taxes & fees
May 22 - May 23
Large duplex king size bed and two queen size
Outdoor pool
Liquid Living On The Lake
9.0 out of 10, Wonderful, (30)
"Stay was amazing and just like the pictures, only small issues was it didn’t get as cold as we liked it, but personal problem! Great stay"
The price is CA $163
CA $231 total
includes taxes & fees
May 27 - May 28
Liquid Living On The Lake
Exterior
Beautiful Downtown Townhome With Attached Garage.
9.0 out of 10, Wonderful, (59)
"This property suited our needs—minimal kitchen, garage for bike storage, walkable to restaurants—but needs a little extra TLC to get it back into top form. A deep cleaning and new, fresh linens (bedding + towels) would go a long way."
The price is CA $157
CA $317 total
includes taxes & fees
May 22 - May 23
Beautiful Downtown Townhome With Attached Garage.
Fridge, microwave, oven, stovetop
RELAX! WORK! PLAY! STAY!
9.0 out of 10, Wonderful, (11)
"The jacuzzi tub helps a lot to relax after exploring Cleveland. The creaky floor throughout the home creates a quant and old-feeling atmosphere even though all the fixtures seem new and top of the line. The trees surrounding the property are fantastically beautiful. It is a quiet street and a quiet house to relax in."
RELAX! WORK! PLAY! STAY!
Exterior
Cal King bed, free parking, by Downtown & Clinic
9.0 out of 10, Wonderful, (10)
"Very good location for walking or public transportation in Cleveland, and good parking. This is a small studio apartment with a kitchenette, the description say both "kitchen and kitchenette" for some reason. The lighting in the room was a little dark, some more light options would be appreciated."
The price is CA $102
CA $191 total
includes taxes & fees
May 26 - May 27
Cal King bed, free parking, by Downtown & Clinic
Don't see what you're looking for?
See all available properties in Chesterland
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.

Other types of properties in Chesterland you may be interested in

Lobby
Drury Plaza Hotel Cleveland Downtown
3.0 star property
9.4 out of 10, Exceptional, (2104)
"Great stay"
The price is CA $172
CA $202 total
includes taxes & fees
Jun 7 - Jun 8
Drury Plaza Hotel Cleveland Downtown
Property amenity
Cleveland Marriott Downtown at Key Tower
4.0 star property
8.8 out of 10, Excellent, (1007)
"Good stay. Comfy beds. The fridge was tiny and covered in ice which made it impossible to store food"
The price is CA $206
CA $242 total
includes taxes & fees
May 30 - May 31
Cleveland Marriott Downtown at Key Tower
Lobby
Extended Stay America Premier Suites - Cleveland - Independence
2.5 star property
7.6 out of 10, Good, (1121)
"I would Definetly stay here again"
The price is CA $116
CA $137 total
includes taxes & fees
May 22 - May 23
Extended Stay America Premier Suites - Cleveland - Independence
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chesterland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Ohio City Getaway! Sleeps 12, Games, Near Downtown: Located near Chesterland, this vacation home rental has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Chesterland?

While exploring the area, visit family-friendly sights like Pioneer Waterland & Dry Fun Park, or get outside and enjoy nature at Chagrin River. 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.

Recent reviews of Chesterland properties
Expedia verified reviews