Chesterfield vacation rentals

We found 66 vacation rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Scroll through and select from vacation rentals in Chesterfield to find one that's perfect for your trip. Whether you're staying in a vacation rental with your kids and pets or just with friends, you'll have the best amenities for spending time at your home away from home, including air conditioning and WiFi. You're sure to find a rental to meet everyone's needs, including options that are accessible or non-smoking.

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Travel to adventurous Chesterfield

The parks and surrounding scenery provide a peaceful ambiance to your vacation home in Chesterfield. This city is well-known for its restaurants and shopping. 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 and around Chesterfield

Are you hoping to find top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Chesterfield a one-of-a-kind vacation spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Berkshire East Ski Resort (15.7 mi / 25.2 km)
  • Elements Hot Tub Spa (16.7 mi / 26.9 km)
  • Land of Providence (9.6 mi / 15.5 km)
  • Lamson and Goodnow (15.4 mi / 24.7 km)
  • Bald Mountain Pottery (16 mi / 25.8 km)
  • Otis Ridge (19 mi / 30.6 km)

Exploring the natural features in Chesterfield

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Chesterfield 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:

  • Look Memorial Park (8.4 mi / 13.5 km)
  • Smith College Botanic Garden (11.3 mi / 18.3 km)
  • October Mountain State Forest (16.8 mi / 27.1 km)
  • Mohawk Trail State Forest (17.8 mi / 28.7 km)
  • Savoy Mountain State Forest (18.9 mi / 30.4 km)
  • Goose Pond Reservation (19.3 mi / 31.1 km)

Traveling to and around Chesterfield

Fly into Westfield, MA (BAF-Barnes Municipal), the closest airport, located 16.6 mi (26.8 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 23.2 mi (37.3 km) away.

Frequently asked questions

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

According to our data, cottages are the most desirable type of property in Chesterfield. But as you know, everyone's idea of an awesome trip will differ. Vrbo has vacation rentals of all shapes and sizes, so you're bound to find your ideal fit.

How much does it cost to rent a vacation rental in Chesterfield?

Different factors influence what you'll pay for a vacation rental in Chesterfield, like the length of stay, season and type of property. Still, all Vrbo homes have something in common — excellent value. Simply enter your travel dates to find your ideal match.

How much does it cost to rent a beach house in Chesterfield?

When you travel and the style and size of the property will help determine the cost of your beachside escape. Enter your Chesterfield travel dates to see your options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use our filters to pick the features and amenities you want in your beach house.

Are there pet-friendly vacation rentals in Chesterfield?

With two properties that welcome four-legged guests, your furry friend can also come along on your Chesterfield break. Use the filter tool to search our pet-friendly vacation rentals and find the pawfect pad on Vrbo.

What are popular rental amenities in Chesterfield?

Mountain views, a fireplace and nearby museums are the most popular rental amenities in Chesterfield. Whether you're taking a trip by yourself, with your sweetheart or a bunch of friends, Vrbo will help you find a vacation home that suits your tastes with all the extras you're looking for.

Are there vacation rentals in Chesterfield that welcome kids?

Chesterfield has two family-friendly vacation rentals to choose from. And discovering a stay that welcomes kids is simple with our "Properties good for families" filter. In addition to having the entire place to yourselves, you'll also enjoy access to perks and conveniences like bunk beds, private pools and yards.

What are the top attractions for families in Chesterfield?

Keep the kids occupied at these fantastic family-friendly attractions in Chesterfield:

  • Glendale Falls
  • Littleville Lake
  • Chapel Brook

How old do you have to be to rent a vacation rental in Chesterfield?

The minimum required age is normally 16, 18 or 21. It can differ across properties on Vrbo, so look at the rules of your preferred Chesterfield vacation home before booking your trip.

How long can I rent a vacation rental in Chesterfield for?

It's down to the Chesterfield property. To browse a list of options offering extended stays, simply enter your dates and guest number into the Vrbo search page. You can enjoy having the place to yourself, along with home comforts such as a fully-equipped kitchen, air conditioning and an outdoor space where your little ones can play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.