Destination guide

The natural setting of Chesterfield is ready to explore

The parks and other outdoor surroundings create an inviting atmosphere in Chesterfield. This city is well-known for its restaurants and shopping. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.


Activities and attractions in and around Chesterfield

Are you hoping to discover attractions to visit during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Chesterfield has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Chesterfield Gorge (1.4 mi / 2.2 km)
  • Becket Land Trust Historic Quarry (12.1 mi / 19.5 km)
  • Bas Ridge Golf Course (13.9 mi / 22.4 km)
  • Hawley Bog Preserve (14.7 mi / 23.7 km)
  • Berkshire East Ski Resort (16.8 mi / 27 km)
  • Otis Ridge (17.7 mi / 28.5 km)
Natural features

Exploring the natural features in Chesterfield

Whether you're an active traveler or just want to spend some time taking in the scenery, Chesterfield is a great spot to appreciate mother nature. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Chesterfield Gorge (1.4 mi / 2.2 km)
  • Look Memorial Park (9.5 mi / 15.3 km)
  • Smith College Botanic Garden (12 mi / 19.4 km)
  • Conway Town Park (12 mi / 19.4 km)
  • Becket Land Trust Historic Quarry (12.1 mi / 19.5 km)
  • Mount Tom (14.4 mi / 23.3 km)
How to get there

How to get to and around Chesterfield

Fly into Westfield, MA (BAF-Barnes Municipal), the closest airport, located 16.5 mi (26.5 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Pittsfield, MA (PSF-Pittsfield Municipal), which is 22.2 mi (35.7 km) away.

How many vacation rentals are available around Chesterfield, MA?

Our 2020 property listings offer a large selection of 40 vacation rentals around Chesterfield. From 8 condo and apartment rentals to 18 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Chesterfield?

Vrbo offers a large selection of vacation rentals near lovely places in Chesterfield. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Chesterfield Gorge: 145 vacation rentals
  • Mount Holyoke College: 68 vacation rentals
  • Western Gateway Heritage State Park: 315 vacation rentals
  • Mount Greylock: 219 vacation rentals
  • Historic Deerfield Village: 77 vacation rentals

But there are many other points of interest around Chesterfield listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Condos/Apartments in Chesterfield?

Yes, of course. Vrbo has 8 Condos/Apartments in Chesterfield. Our other popular types of vacation rentals in Chesterfield include:

  • Houses: 18 rentals available
  • Cabins: 10 rentals available
  • Bungalows: 10 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Cottages and more.

Can I find a vacation rental with pool in Chesterfield?

Yes, you can select your preferred vacation rental with pool among our 3 vacation rentals with pool available in Chesterfield. Please use our search bar to access the selection of vacation rentals available.