Chesterfield holiday rentals

We found 81 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.

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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:

  • 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)
  • Blandford Ski Area (14.1 mi / 22.7 km)
  • Maple Corner Farm Cross Country Ski Area (19.3 mi / 31.1 km)
  • Land of Providence (9.6 mi / 15.5 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)
  • Ashmere Lake (13 mi / 20.9 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

Where are the best Chesterfield ski resort rentals?
For skiing near Chesterfield, the closest ski resorts are located in the nearby Berkshires, particularly in areas like Great Barrington and Pittsfield. In Great Barrington, visitors can find a variety of rental options, including cosy cabins and rustic chalets that cater to both small groups and larger families. Many of these properties feature amenities such as wood-burning stoves, fully equipped kitchens, and outdoor spaces like decks or patios, great for enjoying the winter scenery.In Pittsfield, there are charming townhouses and apartments available, often located within walking distance of local amenities, including shops and restaurants. These accommodations typically offer modern comforts such as Wi-Fi, laundry facilities, and sometimes access to communal areas or fitness centres.Travellers looking for a more secluded experience can explore the surrounding countryside, where secluded cottages provide a tranquil retreat after a day on the slopes. These rentals often come with additional features like hot tubs, fire pits, and picturesque views of the surrounding mountains, ideal for unwinding and enjoying the natural beauty of the area.
What is the most popular type of holiday rental accomodation in Chesterfield?
In Chesterfield, cabins are the most popular type of holiday rental accommodation, with several available throughout the area. These cabins typically offer a rustic charm and are often located in serene, wooded settings, providing guests with a peaceful retreat. Most cabins come equipped with amenities such as fully equipped kitchens, cosy living areas with fireplaces, and outdoor decks or porches, superb for enjoying the natural surroundings. This makes them an ideal choice for families or groups looking to explore the beautiful landscapes of Chesterfield and enjoy outdoor activities.
What are popular rental amenities in Chesterfield?
In Chesterfield, popular holiday rental amenities include features that enhance comfort and convenience for travellers. Many rentals come equipped with kitchens, allowing guests to prepare meals during their stay. Additionally, a dining area is often available for enjoying meals with family or friends. For those who appreciate outdoor space, many properties boast decks or patios, providing a lovely setting to relax and enjoy the surrounding natural beauty. A coffee and tea maker is typically included, ensuring that guests can easily enjoy a warm beverage at any time. Furthermore, the area offers excellent opportunities for hiking, with nearby locations that cater to outdoor enthusiasts.
When is the best time to visit Chesterfield for a holiday rental?
April is the most popular month to visit Chesterfield, Massachusetts, as the spring season brings vibrant blooms and mild weather, creating a friendly space for outdoor exploration. The peak season spans from March to May, attracting visitors who wish to experience the natural beauty of the area and partake in various activities, such as hiking and sightseeing.During this time, temperatures typically range from around 5 to 20 degrees Celsius, offering a comfortable climate for enjoying the picturesque landscapes and local attractions. Chesterfield's scenic hiking trails and charming small-town vibe make it an appealing choice for those seeking a blend of relaxation and adventure.If you're considering a more budget-friendly option, January presents an excellent opportunity to experience Chesterfield's winter charm. During this time, the tranquil atmosphere offers a unique setting for enjoying the beauty of snow-covered landscapes and cozy indoor activities.
What are the top attractions in Chesterfield?
In Chesterfield, Massachusetts, visitors can enjoy a tranquil rural setting characterised by natural beauty and outdoor activities. The nearby Chesterfield Gorge, a part of the Appalachian Trail, offers stunning hiking opportunities with scenic views and well-maintained trails, making it a popular spot for nature lovers.The town is also home to the serene Lake Northampton, where visitors can partake in fishing, kayaking, or simply relaxing by the water. For those interested in local history, the Chesterfield Historical Society is a charming place to learn about the town's past and its role in the region.Additionally, the surrounding Hilltowns provide various opportunities for exploring quaint villages and local artisan shops, enhancing the charm of a stay in Chesterfield.
Are all fees included in the Chesterfield holiday homes prices shown on Stayz?
Stayz 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.
Are there any Chesterfield holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Chesterfield holiday homes?
You can find great discounts on holiday homes in Chesterfield on Stayz, 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.
Can I change or cancel my Chesterfield holiday home booking on Stayz?
To find Chesterfield holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chesterfield?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Chesterfield holiday home?
Book your Chesterfield holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chesterfield?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chesterfield to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.