Chester holiday homes

We found 3 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Chester that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include a fireplace and a washer and dryer. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • 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, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Book a holiday rental for your Chester getaway

Learn about the unique charm of Chester with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Chester

Are you searching for things to do during your stay? Venture out of your holiday home and check out everything that makes Chester a one-of-a-kind holiday spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Four Daughters Vineyard & Winery (16.2 mi / 26.1 km)
  • Deer Creek Speedway (17 mi / 27.4 km)

Exploring the natural features in Chester

Whether you're an adventurous traveller or just want to take in the scenery, Chester is a great place to spend some time outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Forestville Mystery Cave State Park (12.7 mi / 20.4 km)
  • Niagara Cave (15.4 mi / 24.8 km)
  • Root River (24.8 mi / 39.9 km)

Transport options to and around Chester

The nearest airport is in Rochester, MN (RST-Rochester Intl.), located 29.7 mi (47.8 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday home in Chester?
Property type, length of stay and season are some of the things that can affect the price of a holiday home. Simply add your travel dates to find your ideal match. From homey country cottages to expansive luxury villas, all Bookabach holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Chester?
The average price for a holiday home near the beach in Chester depends on when you’re travelling and the size and style of property you’re searching for. You can easily and quickly find prices on Bookabach by entering the dates you’ll be travelling. Then use the handy filter tool to select the number of bedrooms and amenities important to you, like air conditioning, WiFi and a hot tub.
How old do you have to be to rent a holiday home in Chester?
The age limit can differ across properties on Bookabach, so be sure to look at the rules of the holiday home in Chester you want. But usually, it’s 16, 18 or 21.
How long can I rent a holiday home in Chester for?
It’s up to the Chester property. To look over a list of options offering extended stays, just enter your travel dates and number of people into Bookabach. You can enjoy having the place to yourself, along with amenities such as air conditioning, a fully-equipped kitchen and a backyard where the kids can burn off energy. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.