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 trip with friends, holiday 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 holiday 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 centre:

  • 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 traveller 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 centre:

  • 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 centre. 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 holiday rentals are available around Chesterfield?

Our 2020 accommodation listings offer a large selection of 39 holiday lettings around Chesterfield. From 8 flats & apartments to 17 houses, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

What are the most popular points of interest and landmarks to stay near when travelling to Chesterfield? offers a large selection of holiday accommodations near great places in Chesterfield. From travellers, the most popular points of interest to stay near are:

  • Chesterfield Gorge: 142 holiday lettings
  • Hampshire College: 58 holiday lettings
  • Bardwell's Ferry Bridge: 85 holiday lettings
  • Mount Holyoke College: 67 holiday lettings
  • University of Massachusetts-Amherst: 57 holiday lettings

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

Can I rent Flats in Chesterfield?

Yes, of course. offers 8 Flats in Chesterfield. Our other popular types of Chesterfield holiday rentals include:

  • Houses: 17 self catering accommodations
  • Cabins: 10 self catering accommodations
  • Bungalows: 10 self catering accommodations

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

Can I find a holiday accommodation with pool in Chesterfield?

Yes, you can select your preferred holiday accommodation with pool among our 2 holiday homes with pool available in Chesterfield. Please use our search bar to access the selection of holiday rentals available.