Photo by Kristin DePlatchett

Chesterland Holiday Rentals

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Holiday Rentals in Chesterland

Little house on the farm

10.0 out of 10, Exceptional, (90)
"This is our 2nd time staying here. We love the property and all it has to offer!"
The price is AU$331
includes taxes & fees
16 July - 17 July
Little house on the farm

Beautiful cabin situated on wooded land with nice yard clearing and small stream

9.8 out of 10, Exceptional, (8)
"The location was very peaceful and relaxing. We felt at home with nature and enjoyed our time very much!"
The price is AU$254
includes taxes & fees
2 Aug - 3 Aug
Beautiful cabin situated on wooded land with nice yard clearing and small stream

Small town vibes in Garrettsville

10.0 out of 10, Exceptional, (3)
"Very clean, solid rental. "
Small town vibes in Garrettsville

Peaceful Pioneer Place on our Family Farm in Mantua

The price is AU$591
includes taxes & fees
29 July - 30 July
Peaceful Pioneer Place on our Family Farm in Mantua

The Thistle House off Chardon Square

10.0 out of 10, Exceptional, (35)
"Good overall experience. Appreciate the ease of getting into and locking/unlocking door. The house was very clean and met our needs with extremely comfortable beds."
The price is AU$761
includes taxes & fees
17 July - 18 July
The Thistle House off Chardon Square

Family-friendly 5-Star Rated 19th Century Restored Mansion

10.0 out of 10, Exceptional, (32)
"Wonderful property for family gathering."
The price is AU$1,502
includes taxes & fees
29 July - 30 July
Family-friendly 5-Star Rated 19th Century Restored Mansion

Comfy Updated Historic Gem Pets OK 3B Vibrant Area

9.8 out of 10, Exceptional, (63)
"Beautiful home with everything we could need or want. "
The price is AU$457
includes taxes & fees
28 July - 29 July
Comfy Updated Historic Gem Pets OK 3B Vibrant Area

Great Group Getaway: Games Galore + Outdoor Oasis

9.4 out of 10, Exceptional, (13)
"Great property. Really impressed with how clean and comfortable everything was. So much space for our family. Exceeded expectations- will visit again! "
The price is AU$1,226
includes taxes & fees
17 July - 18 July
Great Group Getaway: Games Galore + Outdoor Oasis

Great Group Gathering Spacious 5-bd/2.5 B house 2 Kitchens, Hot Tub, Large Yard

10.0 out of 10, Exceptional, (2)
"Excellent property. Enjoyed our stay"
The price is AU$717
includes taxes & fees
16 July - 17 July
Great Group Gathering Spacious 5-bd/2.5 B house 2 Kitchens, Hot Tub, Large Yard

Cozy Centrally Located Gem-King, Hot Tub, Pets OK, Shops & 15 Mins to Lake Erie

10.0 out of 10, Exceptional, (72)
"We enjoyed our stay here. Happy to have laundry facilities and a hot tub."
The price is AU$543
includes taxes & fees
16 July - 17 July
Cozy Centrally Located Gem-King, Hot Tub, Pets OK, Shops & 15 Mins to Lake Erie

Charming 3-bedroom house in wonderful Moreland Hills with a shared pond & trail

2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a family member’s funeral in this area. This VRBO was in perfect proximity to all we had to do for the weekend. Our immediate family had a wonderful time in the morning having coffee on the back patio watching wildlife around the pond. The house was well equipped with everything we could possibly need."
The price is AU$1,005
includes taxes & fees
19 July - 20 July
Charming 3-bedroom house in wonderful Moreland Hills with a shared pond & trail

Lakefront Oasis Retreat Private Beach-Hot Tub-Pet Friendly-3 Bd/2 B-King Suite

10.0 out of 10, Exceptional, (31)
"We had a great time spending quality family time together in the hot tub, sitting by the fire, grilling out and just listening to the waves! We would definitely return!"
The price is AU$1,028
includes taxes & fees
16 July - 17 July
Lakefront Oasis Retreat Private Beach-Hot Tub-Pet Friendly-3 Bd/2 B-King Suite

Updated Bungalow Near Downtown Willoughby

Updated Bungalow Near Downtown Willoughby

The White House - best view in CVNP

10.0 out of 10, Exceptional, (5)
"This house is perfection. It is a comfortable location to relax, spend time together as a family and explore Cuyahoga National Park. The egg laying chickens were the highlight of the property for my city kids. This property is so lovely. "
The price is AU$886
includes taxes & fees
3 Aug - 4 Aug
The White House - best view in CVNP

Escape to Fun: Hot Tub & Game Arcade Retreat

8.6 out of 10, Excellent, (7)
"The hottub was super clean and very much appreciated after a long day on the road. The house was super clean and the mattress and pillows are the most comfortable ever!!!"
Escape to Fun: Hot Tub & Game Arcade Retreat

Euclid 3 bedroom 1 bath just 12 min to Cleveland

2.0 star property
9.0 out of 10, Wonderful, (2)
"Appreciate the flexibility on the part of the owner/property manager during our stay in Cleveland. "
The price is AU$312
includes taxes & fees
16 July - 17 July
Euclid 3 bedroom 1 bath just 12 min to Cleveland

Luxurious Retreat with Sauna & Modern Design

9.4 out of 10, Exceptional, (6)
"The house had everything you need and is very nicely renovated. The sauna is a big plus. "
The price is AU$915
includes taxes & fees
20 July - 21 July
Luxurious Retreat with Sauna & Modern Design

Relax with the whole family at this peaceful place to stay

Relax with the whole family at this peaceful place to stay

Lake front park near by -15 minutes east of downtown Cleveland

The price is AU$616
includes taxes & fees
28 July - 29 July
Lake front park near by -15 minutes east of downtown Cleveland

Discover Cleveland Heights Charm, Sleeps 12, Pet Friendly, 4BR & 3 Baths

2.0 star property
8.4 out of 10, Very good, (5)
"We came to Cleveland for the Feast. Perfect location!"
The price is AU$900
includes taxes & fees
22 July - 23 July
Discover Cleveland Heights Charm, Sleeps 12, Pet Friendly, 4BR & 3 Baths
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?

Lakefront Escape With Hot Tub & Modern Comforts: This holiday home rental outside of Chesterland is located on a lake, and has a garden, 1 hot tub and air conditioning to put you at ease in your new surroundings. 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 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.