Chester holiday lettings

We found 1,554 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 32 homes 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, 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:

  • Stratton Mountain Resort (19.4 mi / 31.2 km)
  • 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)

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:

  • Jamaica State Park (13.4 mi / 21.6 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)
  • Mt Ascutney State Park (14.9 mi / 24 km)
  • Crescent Lake (17.1 mi / 27.5 km)

Seasonal weather averages in Chester

Travellers enjoy Chester for its skiing. If you're interested in winter sports, you might consider visiting in March, January, November or February, when snowfall averages 46 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 rental?

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, Vrbo is bound to have a holiday property here that's right for you.

What is the most popular type of holiday rental accommodation in Chester?

Houses are the most popular style of holiday rental in Chester, according to our data. Even if you have a different idea about what you want, Vrbo has properties in many shapes and sizes. Browse our options to find your ideal match.

How much does it cost to rent a holiday rental in Chester?

A number of factors can affect the price of a holiday rental 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 rental 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 Vrbo 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 rentals in Chester?

Pack up a suitcase for the pooch in your life because Chester has 35 holiday rentals that throw open their doors to pets. Let your furriest pal join in with the family fun at one of our pet-friendly holiday rentals on Vrbo. 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 rentals and let every day be a pool day. Simply enter your dates into Vrbo, then use the "pool" filter to find the ideal place for a splashing good time!

What are popular rental amenities in Chester?

A water view, ski-in/ski-out facilities and a sauna are rated the most popular rental amenities in Chester. Whether you're taking to the road by yourself, with your other half or a group of friends, Vrbo will help you find a holiday rental that matches your style with all the conveniences you're looking for.

Are there large group holiday rentals 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 rentals 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 rentals in Chester?

Yes, you can take your pick from five one-bedroom rentals 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 rentals 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.

More Holiday Rentals ideas

People also search for