Chester vacation rentals

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your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 32 homes and other vacation rentals in Chester that are perfect for your trip. Vacation rentals offer the best amenities for you and your friends, family, or even pets, such as parking and a fireplace. You're sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

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Why people love visiting cozy Chester

The mountains and surrounding scenery provide a peaceful ambiance to your vacation home in Chester. This relaxing city is known for its hiking, skiing and coffeehouses. 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 hoping to find top things to see and do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Chester a fun place to get away. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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 looking for fun outdoor activities or just want to take in the scenery, Chester is a great place to get outside. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • 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

Travelers 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 18 inches and temperatures average 25°F.

Traveling to and around Chester

Fly into Springfield, VT (VSF-Hartness State), the closest airport, located 6.6 mi (10.7 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly 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 vacation rental?

If you're planning a vacation 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 vacation property here that's right for you.

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

Houses are the most popular style of vacation 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 vacation rental in Chester?

A number of factors can affect the price of a vacation rental in Chester, such as the type of property, length of stay and season. But, all of our vacation 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 vacation 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 traveling. 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 vacation rentals in Chester?

Pack up a suitcase for the pooch in your life because Chester has 35 vacation rentals that throw open their doors to pets. Let your furriest pal join in with the family fun at one of our pet-friendly vacation 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 vacation 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 vacation rental that matches your style with all the conveniences you're looking for.

Are there large group vacation rentals in Chester?

Chester has 11 vacation 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 vacation rentals in Chester that welcome kids?

Gather the whole crew for an adventure in Chester at one of our 35 family-friendly vacation 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 favorite 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 vacation rentals in Chester?

Yes, you can take your pick from five one-bedroom rentals in Chester. Whether you'd prefer a cozy 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 vacation rentals in Chester?

Take off with your besties and enjoy a relaxing escape in one of the four two-bedroom vacation properties Chester has to offer.

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