Destination guide

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. Cleveland Museum of Art and Progressive Field are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.


Activities and attractions in Chesterland

Are you looking for things to do during your stay? Venture out of your cosy holiday rental and experience everything that makes Chesterland a one-of-a-kind holiday spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Fowler's Mill Golf Course (3 mi / 4.9 km)
  • Alpine Valley (3.5 mi / 5.7 km)
  • Sharon James Cellars (6.7 mi / 10.8 km)
  • Chardon Lakes Golf Club (6.9 mi / 11.1 km)
  • StoneWater Golf Club (7.7 mi / 12.4 km)
  • Little Mountain Country Club (9.6 mi / 15.4 km)
Natural features

Exploring the natural landscape of Chesterland

Whether you're looking for adventure or just want to take in the scenery, Chesterland is a great spot to appreciate mother nature. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Lake Metroparks Farmpark (3.4 mi / 5.4 km)
  • North Chagrin Reservation (5.4 mi / 8.8 km)
  • Penitentiary Glen Wildlife Center (5.6 mi / 8.9 km)
  • Punderson State Park (8 mi / 12.8 km)
  • South Chagrin Reservation (9.5 mi / 15.3 km)
  • Cain Park (12.3 mi / 19.7 km)
How to get there

Transport options to and around Chesterland

Fly into Cleveland, OH (CGF-Cuyahoga County), the closest airport, located 8.9 mi (14.3 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Cleveland, OH (BKL-Burke Lakefront), which is 18.3 mi (29.4 km) away.

How many holiday rentals are available around Chesterland?

Our 2020 accommodation listings offer a large selection of 64 holiday lettings around Chesterland. From 31 houses to 17 flats & apartments, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

What are the most popular points of interest and landmarks to stay near when travelling to Chesterland? offers a large selection of holiday accommodations near great places in Chesterland. From travellers, the most popular points of interest to stay near are:

  • Alpine Valley: 117 holiday lettings
  • Fowler's Mill Golf Course: 123 holiday lettings
  • Chalet Debonne Vineyards: 165 holiday lettings
  • Fun 'n' Stuff: 299 holiday lettings
  • Dunham Tavern Museum: 290 holiday lettings

But there are many other points of interest around Chesterland listed on where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Chesterland?

Yes, of course. offers 31 Houses in Chesterland. Our other popular types of Chesterland holiday rentals include:

  • Flats: 17 self catering accommodations
  • Cabins: 4 self catering accommodations
  • Cottages: 4 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including Bungalows and more.

Can I find a holiday accommodation with pool in Chesterland?

Yes, you can select your preferred holiday accommodation with pool among our 13 holiday homes with pool available in Chesterland. Please use our search bar to access the selection of holiday rentals available.