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Top Holiday Rentals in Chesterland

Sleek DT Cleveland Apt at City Club

3.0 star property
9.2 out of 10, Wonderful, (54)
"Excellent property "
Sleek DT Cleveland Apt at City Club

2125 Superior Living

2.0 star property
5.6 out of 10, (26)
"Great place, affordable, and close to attractions"
2125 Superior Living

Barsala At The Monroe Apartments

4.0 star property
9.2 out of 10, Wonderful, (44)
"Clean, quiet, and right next to Little Italy shops and restaurants. A great place to stay. Hoghly recommend! "
Barsala At The Monroe Apartments

Lakefront Escape With Hot Tub & Modern Comforts

10.0 out of 10, Exceptional, (7)
"We enjoyed our time staying at this house! "
Lakefront Escape With Hot Tub & Modern Comforts

Crown royal presidential suite and fitness center

8.8 out of 10, Excellent, (44)
"We had a wonderful time in an interesting place. POSITIVE: Plenty of space, plentiful hot water, first-rate shower-head, basic snack set up with frig, microwave, a big sink area (but with one sink out-of-commission), a comfortable bed, TV, and off-street parking. BUT: Almost nothing is new and you have to co-exist with some supplies like (a mountain of fresh) towels. There is useable desk space, plenty of chairs for a couple, lots of kitchen hardware including a coffee pot with LOTS of coffee,...
The price is £90
includes taxes & fees
30 Jun - 1 Jul
Crown royal presidential suite and fitness center

Cozy Downtown Modern Condo in the Heart of it all

9.6 out of 10, Exceptional, (137)
"Property was extremely close to the venue i was attending. Appropriately priced and very well maintained."
The price is £103
includes taxes & fees
30 Jun - 1 Jul
Cozy Downtown Modern Condo in the Heart of it all

Beach View Suite #8

2.0 star property
The price is £136
includes taxes & fees
30 Jun - 1 Jul
Beach View Suite #8

Luxury Downtown Townhome w/ Private Garage Unit 13

9.6 out of 10, Exceptional, (58)
"Great place to stay!"
The price is £137
includes taxes & fees
1 Jul - 2 Jul
Luxury Downtown Townhome w/ Private Garage Unit 13

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

10.0 out of 10, Exceptional, (57)
"The surrounding are and location were ideal for us to be close to our father who was having open heart surgery at UH Medical Center. They were gracious to permit an early check in. The hot tub, massage recliner & use of washer and dryer were exactly what we needed during this stressful time and the home owners was super friendly during our brief interactions. We can’t recommend this place enough!!!! "
The price is £160
includes taxes & fees
1 Jul - 2 Jul
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!

Coastal Lake Erie Cottage w/ Amazing Water Views!

9.8 out of 10, Exceptional, (19)
"Love the older house feel . The view was amazing ,and the sound of the waves were very relaxing . The host was a pleasure to deal with and communicated well . Would definitely stay again "
Coastal Lake Erie Cottage w/ Amazing Water Views!

Private 2 Level Apartment with Hot Tub in Tremont

9.6 out of 10, Exceptional, (24)
"I really liked the stay nice clean smelled like pine sole will be staying again.. i should have booked for more then one night"
The price is £131
includes taxes & fees
7 Jul - 8 Jul
Private 2 Level Apartment with Hot Tub in Tremont

Large duplex king size bed and two queen size

9.2 out of 10, Wonderful, (51)
"We really enjoyed our stay. "
The price is £150
includes taxes & fees
6 Jul - 7 Jul
Large duplex king size bed and two queen size

Hot Tremont House - 6 Bed 3 Bath

9.8 out of 10, Exceptional, (6)
"The house was clean and vibrant! Great atmosphere!"
The price is £553
includes taxes & fees
30 Jun - 1 Jul
Hot Tremont House - 6 Bed 3 Bath

CLE BNB Getaway ★ 15 Guests ★ Stunning Kitchen ★ Game Room ★ Big Fenced Yard

8.6 out of 10, Excellent, (75)
"Easy access and great location "
The price is £245
includes taxes & fees
1 Jul - 2 Jul
CLE BNB Getaway ★ 15 Guests ★ Stunning Kitchen ★ Game Room ★ Big Fenced Yard

Forever spring cabin

10.0 out of 10, Exceptional, (216)
"Our second time here and as good as the first. Very quiet and cozy. Would recommend."
Forever spring cabin

Mid Century Guest House on Wooded Lot

10.0 out of 10, Exceptional, (45)
"We really like it was very clean and people was very friendly "
Mid Century Guest House on Wooded Lot

Timeless Tremont-2 Bdrm near Downtown Cle

2.0 star property
10.0 out of 10, Exceptional, (19)
"Great time, couldn’t ask for anything else. The rooms were comfy and clean. Again, very much enjoyed our time there."
The price is £149
includes taxes & fees
30 Jun - 1 Jul
Timeless Tremont-2 Bdrm near Downtown Cle

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

9.4 out of 10, Exceptional, (60)
"This is our 2nd time staying here and it did not disappoint. The neighborhood is nice and quiet with a lots to do within walking distance or a short drive. We highly recommend. "
The price is £150
includes taxes & fees
20 Jul - 21 Jul
Lovely in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

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

10.0 out of 10, Exceptional, (37)
"Great location, helpful and responsive host."
The price is £184
includes taxes & fees
28 Jul - 29 Jul
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!

Spacious Home Chef's Kitchen, BBQ Grill, 5 Min Cle Clinic, Hot Tub, ADA, King

10.0 out of 10, Exceptional, (3)
"Amazing communication, hosts, home, family get-a-way (with some work in the area). This is a gem in Cleveland! Quiet, peaceful and hope to be able to stay again when we come to the area. Pictures of home are beautiful but the home & ambiance you just have to experience yourself."
The price is £653
includes taxes & fees
2 Jul - 3 Jul
Spacious Home Chef's Kitchen, BBQ Grill, 5 Min Cle Clinic, Hot Tub, ADA, King
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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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 West Geauga Plaza 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.