Chester holiday rentals

We found 1,586 holiday rentals — enter your dates for availability

Discover a selection of 32 homes, 10 cabins and other holiday rentals in Chester that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as a fireplace and garden. You'll be able to choose a property to rent that has what everyone needs, including options that are 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

Why people love visiting cosy Chester

The mountains and surrounding scenery provide a peaceful ambience to your holiday home in Chester. This relaxing city is known for its hiking, skiing and coffee shops. 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 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 spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Vermont Country Store (6.4 mi / 10.3 km)
  • Magic Mountain Ski Resort (9.7 mi / 15.6 km)
  • Viking Nordic Center (9.9 mi / 15.9 km)
  • Okemo Mountain Resort (11.4 mi / 18.3 km)
  • Fox Run Golf Course (11.8 mi / 19.1 km)
  • Jamaica State Park (13.4 mi / 21.6 km)

Exploring the natural features in Chester

Whether you're an adventurous traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Chester. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Lowell Lake State Park (9 mi / 14.5 km)
  • Buttermilk Falls (13.8 mi / 22.1 km)
  • Lake Rescue (14.1 mi / 22.7 km)
  • Mount Ascutney (14.4 mi / 23.1 km)
  • Winhall River (14.8 mi / 23.7 km)
  • Echo Lake (15.5 mi / 25 km)

Seasonal weather averages in Chester

Travellers enjoy Chester for its skiing. If you're interested in winter sports, you might consider visiting in January, March, November or February, when snowfall averages 35 cm and temperatures average -4°C.

Travelling to and around Chester

Fly into Springfield, VT (VSF-Hartness State), the closest airport, located 6.6 mi (10.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.4 mi (40.8 km) away.

Frequently asked questions

What is the best area to stay in Chester when booking a holiday home?
If you're planning a holiday in Chester, Chester Depot is among the most sought-after locations to stay. No matter your style of travel, Stayz is bound to have a holiday property here that's right for you.
What is the most popular type of holiday home accommodation in Chester?
Houses are the most popular style of holiday home in Chester, according to our data. Even if you have a different idea about what you want, Stayz has properties in many shapes and sizes. Browse our options to find your ideal match.
How much does it cost to rent a holiday home in Chester?
A number of factors can affect the price of a holiday home in Chester, such as the type of property, length of stay and season. But, all of our holiday homes have one thing in common — unbeatable value. Just add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Chester?
The average price for a holiday home close to the beach in Chester will depend on when you're going and the type and size of property you're looking for. You can easily find prices on Stayz by entering the dates you'll be travelling. Then use the filter tool to choose the number of bedrooms and amenities important to you, such as a pool, air conditioning and WiFi.
Are there pet-friendly holiday homes in Chester?
Pack up a suitcase for the pooch in your life because Chester has 35 holiday homes that throw open their doors to pets. Let your furriest pal join in with the family fun at one of our pet-friendly holiday homes on Stayz. Simply enter your travel dates then check our "Pets allowed" filter box.
Can I rent a house with a pool in Chester?
Pack your swimwear and inflatable flamingo, because there are six houses with a private pool in Chester. Unwind at one of these sought-after holiday homes and let every day be a pool day. Simply enter your dates into Stayz, then use the "pool" filter to find the ideal place for a splashing good time!
What are popular home amenities in Chester?
A water view, ski-in/ski-out facilities and a sauna are rated the most popular home amenities in Chester. Whether you're taking to the road by yourself, with your other half or a group of friends, Stayz will help you find a holiday home that matches your style with all the conveniences you're looking for.
Are there large group holiday homes in Chester?
Chester has 11 holiday properties that can host 10 or more guests. These stays come with plenty of space to share good times with friends and family.
Are there holiday homes in Chester that welcome kids?
Gather the whole crew for an adventure in Chester at one of our 35 family-friendly holiday properties. A lot of these stays come with amenities that are great for getaways with the little ones, like laundry facilities, extra bedrooms and patios. Simply click on the "Properties good for families" filter box and choose your favourite option.
What are the top attractions for families in Chester?
If you're seeking some fun for the whole family close to the heart of Chester, make sure to visit DaVallia Art & Accents.
Are there one-bedroom holiday homes in Chester?
Yes, you can take your pick from five one-bedroom homes in Chester. Whether you'd prefer a cosy chalet or a cabin, our one-bedroom properties are perfect if you don't require a huge amount of space. One of the major perks of having your own pad? You won't have to share your trip with strangers.
Can I find two-bedroom holiday homes in Chester?
Take off with your besties and enjoy a relaxing escape in one of the four two-bedroom holiday properties Chester has to offer.
Are there holiday homes with WiFi in Chester?
Take your pick of 21 holiday homes with WiFi in Chester. If you want to disconnect from daily life during your trip, but still want to be connected to the internet, these properties have just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Chester?
Chester has 20 holiday homes where you can unwind in air-conditioned comfort. To locate a property on Stayz that has this amenity, enter your travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Chester?
Age restrictions can differ across properties on Stayz, so check the rules of the holiday home in Chester you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday home in Chester for?
The amount of time you can book a Chester holiday home for is down to the property. Just tap in your preferred travel dates to view available options offering longer term stays. They include everything you need to make your extended getaway more comfortable like kitchens and air conditioning. Some properties may also offer weekly or monthly discounted prices, so you can have a longer stay for less.

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