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Chesterland Vacation Rentals

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Vacation Rentals in Chesterland

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!
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
Jun 3 - Jun 4
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."
The price is CA $272
CA $548 total
includes taxes & fees
May 20 - May 21
RIVERFRONT Cottage-Hot Tub, Billiards, Golf Cart, Pet Friendly
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Smart TV, fireplace, books, stereo
Mid Century Guest House on Wooded Lot
10.0 out of 10, Exceptional, (21)
"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
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
Property grounds
Tremont 1BR Pet Friendly, Private w/dedicated workspace and soaking tub!
10.0 out of 10, Exceptional, (14)
"Tammy and Frank were great hosts! Super friendly and very communicative which made the process a breeze. This place was perfect for a quick weekend getaway. We will definitely be back!"
The price is CA $175
CA $233 total
includes taxes & fees
Jun 3 - Jun 4
Tremont 1BR Pet Friendly, Private w/dedicated workspace and soaking tub!
Exterior
The Thistle House off Chardon Square
10.0 out of 10, Exceptional, (21)
"Very clean and beautiful place to stay. We would definitely recommend."
The price is CA $401
CA $677 total
includes taxes & fees
May 19 - May 20
The Thistle House off Chardon Square
Fridge, microwave, oven, stovetop
Ohio City Getaway W/ Hot Tub, Pool Table and more!
9.8 out of 10, Exceptional, (37)
"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!
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 $124
CA $274 total
includes taxes & fees
May 22 - May 23
Downtown Sq: Stadium, Casino, Rock Hall, Clinic
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 $224 total
includes taxes & fees
Jun 5 - Jun 6
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 21 - May 22
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, (24)
"This property was clean with friendly and easy to understand communication from the host. We spent most of our time enjoying the amenities of the city, and this property had great access to lots of museums for my children and I to go to, and had just the right amount of space for us to settle in after a busy day experiencing Cleveland. Loved the games made available by the host, and we took the opportunity to play Yahtzee several times."
Perfect! near Cleveland Clinic, CWRU, UH, Downtown & Sports venues w/Porch!
View from room
ROOST Cleveland
4.0 star property
9.6 out of 10, Exceptional, (221)
"Very clean and beautiful apartment. Near many restaurants and attractions. I would definitely recommend. "
The price is CA $285
CA $334 total
includes taxes & fees
May 28 - May 29
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 $239 total
includes taxes & fees
May 19 - May 20
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 $102
CA $225 total
includes taxes & fees
May 21 - May 22
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 $283 total
includes taxes & fees
Jun 4 - Jun 5
Large duplex king size bed and two queen size
Outdoor pool
Liquid Living On The Lake
9.0 out of 10, Wonderful, (29)
"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 $233 total
includes taxes & fees
Jun 3 - Jun 4
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 $320 total
includes taxes & fees
May 19 - May 20
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!
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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, (2088)
"I always enjoy staying at the Drury. It is in a cool building that used to be the 1920 Cleveland Board of Education Building, and has the free breakfast and 5:30 kickback. My only issue this time was the room cleanliness. The edges around the room had dirt, crumbs, and even a straw. It bothered me and made me question the cleanliness of the bed and everything else in the room quite frankly. I'm hoping that this was just a one time miss, so I feel comfortable coming back."
The price is CA $172
CA $202 total
includes taxes & fees
May 23 - May 24
Drury Plaza Hotel Cleveland Downtown
Terrace/patio
Hotel Indigo Cleveland Downtown, an IHG Hotel
3.5 star property
8.6 out of 10, Excellent, (1121)
"Was noisy on the street side but extremely close to the Ro jet Mortgage centre so was perfect. So close and staff were lovely. "
The price is CA $184
CA $216 total
includes taxes & fees
May 24 - May 25
Hotel Indigo Cleveland Downtown, an IHG Hotel
Lobby
Extended Stay America Premier Suites - Cleveland - Independence
2.5 star property
7.6 out of 10, Good, (1117)
"I would Definetly stay here again"
The price is CA $116
CA $137 total
includes taxes & fees
Jun 6 - Jun 7
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