Chester holiday rentals

We found 48 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 rental with your children or with friends, you'll find the amenities that you need and want, such as Wi-Fi and cable TV. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.
  • 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

Choose 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 and around Chester

Are you searching for attractions to visit during your stay? Venture out of your holiday home and experience everything that makes Chester a fun place to get away to. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Jato Highlands Golf Course (1.3 mi / 2.1 km)
  • Mt. Jefferson (11.3 mi / 18.1 km)
  • Hillcrest Golf Club (20 mi / 32.1 km)

Exploring the natural landscape of Chester

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

  • Schoodic Lake (20.6 mi / 33.2 km)
  • South Twin Lake (22.9 mi / 36.8 km)
  • Pleasant River (26.8 mi / 43.1 km)

Travelling to and around Chester

The nearest airport is in Millinocket, ME (MLT-Millinocket Municipal), located 18.9 mi (30.4 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Bangor, ME (BGR-Bangor Intl.), which is 44.3 mi (71.2 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Chester?
The most popular types of holiday homes in Chester are cottages. Ready for more choices? Stayz offers a variety of options to match the unique needs of our guests, so you’ll see holiday properties in all sizes and shapes. The ideal fit is ready and waiting for you — find yours today.
How much does it cost to rent a holiday home in Chester?
A range of things can affect what you’ll pay for your holiday home in Chester, such as the length of stay, season and type of property. However, all Stayz homes have something in common — exceptional value. Just enter your travel dates to find your perfect fit.
How much does it cost to rent a beach house in Chester?
Prices for beach houses in Chester differ depending on the style and size of the property and when you plan to travel. Just enter your travel dates into Stayz and the number of guests to view your holiday home options and prices. From there you can use our filter tool to refine your search by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday homes in Chester?
With two holiday homes that welcome four-legged guests, your happy hound can also come along on your Chester holiday. Use our filter tool to browse our pet-friendly holiday homes and find your pawfect digs on Stayz.
What are popular home amenities in Chester?
When it comes to home amenities that people look for in Chester, a nearby waterfront, a nearby river and a garden rank the highest. With Stayz holiday homes, you’ll discover options to match your style and taste, whether you’re going on a trip with relatives, friends or even pets.
Are there holiday homes in Chester that welcome kids?
Chester has two family-friendly holiday homes. And finding a stay that welcomes kiddos is easy with Stayz’s “Properties good for families” filter. In addition to having the whole place to yourselves, you’ll also get amenities and perks like bunk beds, full kitchens and yards.
What are the top attractions for families in Chester?
Treat the kiddos to a day out at these wonderful family-friendly attractions in Chester:

  • Lincoln Memorial Library
  • Jato Highlands Golf Course

How old do you have to be to rent a holiday home in Chester?
The age limit can differ across properties on Stayz, so double-check the rules of the holiday home in Chester you’re interested in. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home in Chester for?
It really depends on the Chester property. To view all available options offering extended stays, simply type your dates and number of people into Stayz’s search page. Look forward to having the property to yourself, along with amenities such as air conditioning, a kitchen and a backyard where your little ones can play. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.

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