Discover a selection of 39 holiday rentals in Chesterfield, MA, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 129 per night, and houses and flats & apartments are popular options for a stay in Chesterfield. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Chesterfield
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.

Can I find a vacation rental around Chesterfield?

Yes, our 2021 property listings offer a large selection of 39 vacation rentals near Chesterfield. From 25 houses to 8 flats & apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chesterfield for a holiday or a weekend are on Vrbo.

Can I rent Houses in Chesterfield?

Yes, of course. Vrbo UK has 25 Houses in Chesterfield. Our other popular types of vacation rentals in Chesterfield include:

  • Flats: 8 rentals available
  • Cabins: 9 rentals available
  • Cottages: 9 rentals available

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

Can I find a vacation rental with pool in Chesterfield?

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