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Holiday Rentals in Chesterland

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Holiday Rentals in Chesterland

2125 Superior Living

2.0 star property
6.0 out of 10, (33)
"Loved the decor, vey clean, has everything you need. Very close to downtown, just a few bus stops away. "
2125 Superior Living

Sleek DT Cleveland Apt at City Club

3.0 star property
9.2 out of 10, Wonderful, (83)
"lover the property will stay again next time I'm in the Cleveland area. "
Sleek DT Cleveland Apt at City Club

Cozy Downtown Modern Condo in the Heart of it all

9.6 out of 10, Exceptional, (141)
"Had such a great time, so close to all the best attractions. Would stay again!"
The price is €121
includes taxes & fees
24 Aug - 25 Aug
Cozy Downtown Modern Condo in the Heart of it all

Crown royal presidential suite and fitness center

8.8 out of 10, Excellent, (46)
"I spent a couple of days there, basically everything is fine, despite the fact that initially there were problems with entering the house, this problem was solved (I think this is not constant and other visitors will not have this problem). The area is really quiet, there is also a small store near the house. The owner is quite friendly and responsive, everything was in the house, but he could not turn on the TV, I hope this problem will be solved and in the future no one will encounter this...
The price is €106
includes taxes & fees
24 Aug - 25 Aug
Crown royal presidential suite and fitness center

Luxury Downtown Townhome w/ Private Garage Unit 13

9.6 out of 10, Exceptional, (68)
"Very clean and convenient "
The price is €170
includes taxes & fees
21 Aug - 22 Aug
Luxury Downtown Townhome w/ Private Garage Unit 13

The Farm at Grand River

7.4 out of 10, Good, (3)
"Excellent spot to camp, very peaceful. We would definitely revisit if we are in the area again. Property manager(s) were very friendly and accommodating."
The price is €47
includes taxes & fees
29 Aug - 30 Aug
The Farm at Grand River

Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!

9.8 out of 10, Exceptional, (39)
"Great location, helpful and responsive host."
The price is €184
includes taxes & fees
11 Sept - 12 Sept
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!

Coastal Lake Erie Cottage w/ Amazing Water Views!

9.6 out of 10, Exceptional, (20)
"We had a lovely time. The view is the best!"
Coastal Lake Erie Cottage w/ Amazing Water Views!

Hot Tremont House - 6 Bed 3 Bath

9.6 out of 10, Exceptional, (9)
"We had a great time during our stay. The house had everything we needed for the evening. "
The price is €690
includes taxes & fees
20 Aug - 21 Aug
Hot Tremont House - 6 Bed 3 Bath

Beach View Suite #8

2.0 star property
9.0 out of 10, Wonderful, (2)
"Would recommend. We were in town for a 93rd birthday party and it was perfect for what we needed. Quick walk to beach, ice cream and diner. Provided all we needed"
The price is €160
includes taxes & fees
24 Aug - 25 Aug
Beach View Suite #8

Enormous Group Retreat - King Bed, Game Room, Private Yard, Near Downtown CLE!

8.6 out of 10, Excellent, (78)
"Enjoyed our stay.Only complaint, really, was that one of the bunk bedrooms only exit was through the master bedroom. Not a big deal.Home is old, it well kept. "
The price is €299
includes taxes & fees
26 Aug - 27 Aug
Enormous Group Retreat - King Bed, Game Room, Private Yard, Near Downtown CLE!

Casual CLE: 1 bdrm near Downtown Cle

8.6 out of 10, Excellent, (7)
"Went to CLE for the NCAA tournament. Location was great so close to Rocket Arena. Easy walk to the Rowley Inn featured on Triple D. Quiet neighborhood, easy street parking. Kia was very responsive and the apartment well decorated."
The price is €149
includes taxes & fees
20 Aug - 21 Aug
Casual CLE: 1 bdrm near Downtown Cle

Gordon Square Studio ~ 4 Mi to Downtown Cleveland!

3.0 star property
10.0 out of 10, Exceptional, (4)
"Lovely stay - comfortable studio, communicative host, great location, and easy parking. "
Gordon Square Studio ~ 4 Mi to Downtown Cleveland!

Enjoy this historic charming spacious clean One-bedroom Apartment. Pet Friendly

5.8 out of 10, (23)
"Classic Cleveland Hts. apartment- spacious, solid. Had everything we needed and questions were answered promptly ~ Thanks! "
The price is €115
includes taxes & fees
20 Aug - 21 Aug
Enjoy this historic charming spacious clean One-bedroom Apartment. Pet Friendly

3 BR Home in South Cleveland w Easy Access to Cleveland Clinic, UH Hospitals, Hopkins Airport

10.0 out of 10, Exceptional, (2)
"The manager did an amazing job at helping us find the place. Great accommodation and great service. A"
The price is €205
includes taxes & fees
20 Aug - 21 Aug
3 BR Home in South Cleveland w Easy Access to Cleveland Clinic, UH Hospitals, Hopkins Airport

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

9.8 out of 10, Exceptional, (48)
"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 . "
The price is €158
includes taxes & fees
1 Sept - 2 Sept
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!

10.0 out of 10, Exceptional, (64)
"We absolutely loved our stay. Location was perfect for us to take in the Feast and enjoy neighborhood, restaurants and shopping. Our host was incredible and even took the time to message me and let me know that I had left behind some perishable goodies in the refrigerator. We are in the area often and will most definitely stay here again."
The price is €188
includes taxes & fees
20 Aug - 21 Aug
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!

Timeless Tremont-2 Bdrm near Downtown Cle

2.0 star property
9.6 out of 10, Exceptional, (24)
"I loved the stay it was very relaxing and it was in a great location "
The price is €236
includes taxes & fees
13 Sept - 14 Sept
Timeless Tremont-2 Bdrm near Downtown Cle

Exclusive Luxury Penthouse - Heart of Downtown Cleveland - Rare Find

10.0 out of 10, Exceptional, (26)
"We stayed for a quick overnight trip downtown with friends and the penthouse was perfect. Clean and great location!"
Exclusive Luxury Penthouse - Heart of Downtown Cleveland - Rare Find

Luxurious 3-BR Lakefront Cottage on Lake Erie - Book Your Lakeside Retreat Today

10.0 out of 10, Exceptional, (91)
"Wonderful place. Clean and peaceful. "
Luxurious 3-BR Lakefront Cottage on Lake Erie - Book Your Lakeside Retreat Today
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

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. West Geauga Plaza and West Geauga Public Library 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.