Chesterfield holiday lettings

We found 78 holiday rentals — enter your dates for availability

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:13 Mar - 20 Mar

Image gallery for Hill Ross Guest Suite on Historic Homestead

Exterior
10 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)

Hill Ross Guest Suite on Historic Homestead

Florence, MA

12% off
Price is £2,904
for 7 nights, 1 home
£415 per night
includes taxes & fees
Hill Ross Guest Suite on Historic Homestead

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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:

  • Central Rock Climbing Center (13.4 mi / 21.6 km)
  • Blandford Ski Area (14.1 mi / 22.7 km)
  • 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)
  • Maple Corner Farm Cross Country Ski Area (19.3 mi / 31.1 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)
  • Littleville Lake (8.2 mi / 13.3 km)
  • Look Memorial Park (8.4 mi / 13.5 km)
  • Bullitt Reservation (8.8 mi / 14.1 km)
  • Ashfield Lake (9.9 mi / 16 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 best area to stay in Chesterfield when booking a holiday rental?
When considering a holiday rental in Chesterfield, Massachusetts, the area surrounding the picturesque village centre is an excellent choice. This charming neighbourhood offers a delightful blend of scenic beauty and local attractions, making it ideal for a relaxing getaway. One of the highlights of this area is the proximity to the Chesterfield Gorge, a stunning natural area where you can enjoy hiking trails and breathtaking views of the gorge itself. This natural beauty invites you to explore the outdoors and appreciate the serene environment.
How much does it cost to rent a holiday home in Chesterfield?
Prices for holiday rentals in Chesterfield vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chesterfield to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chesterfield holiday house rentals?
You can find great discounts on house rentals in Chesterfield on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Chesterfield ski resort rentals?
For those seeking ski resort rentals near Chesterfield, Massachusetts, the closest great skiing area is at Berkshire East Mountain Resort, situated around 30 minutes away in Charlemont. This resort offers a variety of winter activities, and travellers can find accommodations in nearby towns such as Charlemont and Buckland.

In Charlemont, visitors will discover charming cabins and lodges that cater to winter sports enthusiasts. Many properties here come equipped with essential amenities such as fireplaces, fully stocked kitchens, and spacious living areas, providing a warm and inclusive setting after a day on the slopes. Some rentals even offer outdoor decks with scenic views of the surrounding mountains.

In Buckland, the accommodations tend to be more rustic, with options like traditional New England homes and cosy cottages. These properties often feature amenities like hot tubs, which are superb for soothing sore muscles after a day of skiing, along with easy access to nearby trails for snowshoeing or cross-country skiing.
What is the most popular type of holiday rental accomodation in Chesterfield?
In Chesterfield, cabins are the most popular type of holiday rental, with several available throughout the area. These cabins typically provide a rustic charm, featuring spacious interiors, fully equipped kitchens, and comfortable living areas designed for relaxation after a day of exploring the picturesque surroundings. Many cabins also include amenities like fire pits, outdoor decks, and scenic views of the nearby woodlands and hills, making them ideal for families and groups seeking a peaceful retreat in nature.
Can I find long-stay holiday rentals in Chesterfield?
A long-stay holiday rental in Chesterfield is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Chesterfield holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chesterfield with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chesterfield?
In Chesterfield, popular rental amenities include well-equipped kitchens, which allow guests to prepare their own meals with ease. Most properties feature essential cookware, dishware, and utensils, ensuring a convenient cooking experience. Many rentals also provide a refrigerator for storing food and drinks, and some offer coffee makers in the room for that early morning brew. Additionally, guests can enjoy lovely mountain views from their accommodations, enhancing the tranquil atmosphere of this picturesque area.
When is the best time to visit Chesterfield for a holiday rental?
April is the most popular time to visit Chesterfield, as it marks the vibrant peak season running from March to May. During this time, nature awakens, and visitors can experience firsthand the beauty of blooming wildflowers and lush greenery. The warmer temperatures, typically reaching the low 15s Celsius, make it an ideal period for outdoor activities like hiking and exploring the charming local trails, superb for those seeking a connection with nature.

With the arrival of spring, Chesterfield offers a delightful atmosphere for both adventure seekers and those looking to relax. The region's scenic landscapes provide opportunities for sightseeing, and you might even catch a glimpse of local wildlife as you stroll through the picturesque surroundings.

If you're looking for a more budget-friendly option, consider visiting in January. It's cooler, this quieter month allows you to enjoy the peaceful beauty of Chesterfield's winter landscape, and you may find better deals on holiday rentals.
How early should I book a Chesterfield holiday rental?
Book your Chesterfield holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Chesterfield home rental booking on Vrbo?
To find Chesterfield holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chesterfield holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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