Chesterfield holiday homes, MA, USA: holiday houses & more

Scroll through and select from holiday rentals in Chesterfield to find one that's perfect for your trip. Whether you're staying in a holiday rental with friends, family or just with your pet, you'll find the amenities that you need and want, which might include Wi-Fi and a fireplace. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Chesterfield

Showing deals for:25 Jul - 1 Aug

Exceptional

(53 reviews)

Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

Middlefield, MA

12% off

NZ$812 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Chesterfield

Elegant Wilderness Cabin 12 Miles From Northampton

Sleeps 4 · 2 bedrooms · 1 bathroom

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Travel to adventurous Chesterfield

The parks and surrounding scenery provide a peaceful ambience to your holiday 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 discover attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Chesterfield a fun place to get away to. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Berkshire East Ski Resort (15.7 mi / 25.2 km)
Elements Hot Tub Spa (16.7 mi / 26.9 km)
Otis Ridge (19 mi / 30.6 km)
Land of Providence (9.6 mi / 15.5 km)
Congregation Beth Israel (10.4 mi / 16.7 km)
Blandford Ski Area (14.1 mi / 22.7 km)

Exploring the natural features in Chesterfield

Whether you're an active traveller or just want to appreciate the scenery, Chesterfield is a great place to get outside. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

Chesterfield Gorge (2.1 mi / 3.4 km)
Swift River (4.4 mi / 7.1 km)
Glendale Falls (7.1 mi / 11.5 km)
Look Memorial Park (8.4 mi / 13.5 km)
Smith College Botanic Garden (11.3 mi / 18.3 km)
Iroquis Waterfront (13.8 mi / 22.2 km)

Travelling to and around Chesterfield

Fly into Westfield, MA (BAF-Barnes Municipal), the closest airport, located 16.6 mi (26.8 km) from the city centre. If you can't find a flight that's convenient for your trip, 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 holiday home 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. Bookabach has holiday homes of all shapes and sizes, so you’re bound to find your ideal fit.

How much does it cost to rent a holiday home in Chesterfield?

Different factors influence what you’ll pay for a holiday home in Chesterfield, like the length of stay, season and type of property. Still, all Bookabach 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 Bookabach. 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 holiday homes 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 holiday homes and find the pawfect pad on Bookabach.

What are popular home amenities in Chesterfield?

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

Are there holiday homes in Chesterfield that welcome kids?

Chesterfield has two family-friendly holiday homes 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 holiday home in Chesterfield?

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

How long can I rent a holiday home 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 Bookabach 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.