Photo by Kristin DePlatchett

Chesterland holiday lettings

We found 134 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Chesterland that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, such as air conditioning and a TV. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.
  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Book a holiday rental for your Chesterland getaway

Learn about the unique charm of Chesterland with a stay in a holiday home rental. This city is well-known for its golfing and skiing. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Chesterland

Do you want to find attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Chesterland a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Fowler's Mill Golf Course (3.3 mi / 5.4 km)
  • StoneWater Golf Club (7.4 mi / 11.9 km)
  • Thistledown Racetrack (11.7 mi / 18.8 km)
  • Pioneer Waterland & Dry Fun Park (13.2 mi / 21.3 km)
  • MGM Northfield Park (15.4 mi / 24.8 km)
  • Fun 'n' Stuff (17.5 mi / 28.2 km)

Exploring the natural landscape of Chesterland

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Chesterland is a great place to get outside. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Lake Metroparks Farmpark (4.1 mi / 6.5 km)
  • The Holden Arboretum (6.5 mi / 10.5 km)
  • Punderson State Park (8 mi / 12.9 km)
  • Chagrin River (10 mi / 16.1 km)
  • Cain Park (11.5 mi / 18.5 km)
  • Euclid Beach (12.7 mi / 20.4 km)

Transport to and around Chesterland

Fly into Cleveland, OH (CGF-Cuyahoga County), the closest airport, located 8.6 mi (13.8 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Cleveland, OH (BKL-Burke Lakefront), which is 17.7 mi (28.5 km) away.

Frequently asked questions

How much does it cost to rent a holiday rental in Chesterland?
The average price for a holiday home in Chesterland depends on a number of factors, including property type, season and length of stay. Whether you prefer a sprawling villa with space for extended family or a quaint cottage for you and your other half, just enter your travel dates to see stays with terrific value.
How much does it cost to rent a beach house in Chesterland?
The average price for a holiday rental close to the beach in Chesterland depends on when you’re visiting the area and the style and size of property you’re looking for. You can find prices easily and quickly on Vrbo by entering the dates you’ll be travelling. Then use our handy filter tool to select the number of bedrooms and amenities that you require, like air conditioning, a pool and WiFi.
What are the top attractions for families in Chesterland?
Keeping the kids amused during your holiday in Chesterland is child’s play with these family-friendly attractions:

  • Lake Lucerne Beach
  • Chardon Lakes Golf Club
  • Fowlers Mill Golf Course

How old do you have to be to rent a holiday rental in Chesterland?
The minimum age allowed can differ across properties on Vrbo, so look at the rules of the holiday home in Chesterland you want. But typically, it’s 16, 18 or 21.
How long can I rent a holiday rental in Chesterland for?
The amount of time you can book a Chesterland holiday home for is up to each property. Simply enter your preferred travel dates to view available options offering longer term stays. They include all you require to make your extended trip more comfortable and enjoyable, like air conditioning and laundries. Some properties may also offer weekly or monthly discounts, so you can hang around longer for less.

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