Chesterfield vacation rentals

We found 79 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Chesterfield to find one that's perfect for your trip. Whether you're staying in a vacation rental with your kids and pets or just with friends, you'll have the best amenities for spending time at your home away from home, including air conditioning and WiFi. You're sure to find a rental to meet everyone's needs, including options that are accessible or non-smoking.

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Find out more about Chesterfield

Why visit Chesterfield

  • Beautiful outdoor spaces: Chesterfield boasts stunning landscapes, perfect for hiking and family-friendly activities.
  • Cultural experiences: Explore the mix of historic and modern colleges and universities in the area.
  • Charming neighborhoods: Discover nearby towns in New Hampshire with friendly locals and a relaxing atmosphere.
  • Diverse accommodations: Choose from cozy cottages, stylish apartments, and spacious vacation homes for a comfortable stay.
  • Adventure and tranquility: Enjoy adventure-filled days followed by peaceful evenings soaking in the natural beauty.

Popular types of accommodation in Chesterfield

Planning your getaway to Chesterfield? Discover the charm of the area by choosing from a variety of vacation rentals. Whether you prefer cozy cottages, stylish apartments, or spacious houses, you’ll find the perfect spot to unwind. Look for inviting holiday cottages with hardwood floors or explore our selection of new properties and cottage apartments. Your ideal Chesterfield escape awaits.

  • Houses: The top choice for visitors to Chesterfield, offering spacious accommodations ideal for families or groups seeking comfort and privacy.
  • Apartments: A great option for those looking for a convenient and home-like atmosphere during their stay in Chesterfield.
  • Cottages: These charming retreats provide a warm and cozy environment, perfect for a romantic getaway or a peaceful escape.
  • Cabins: Rustic and inviting, cabins are perfect for nature enthusiasts wanting to immerse themselves in the great outdoors.
  • Condos: A modern choice that combines amenities and location, offering a stylish stay close to local attractions.**

Top attractions in and around Chesterfield

Chesterfield, Massachusetts, is the perfect destination for outdoor enthusiasts and adventure seekers. Visitors can explore a mix of historic and modern colleges and universities, along with nearby national and state parks. The area's attractions cater to those looking for family experiences and cultural activities, making it an ideal spot for a memorable vacation. Whether you're traveling solo or with loved ones, Chesterfield offers a unique blend of scenery and adventure.

  • Smith College: A historic women's college known for its stunning architecture and beautiful gardens, Smith College offers a rich cultural experience. Explore the Smith College Museum of Art and enjoy the vibrant atmosphere of this academic hub located 11 miles from Chesterfield.
  • University of Massachusetts Amherst: A large, modern university with a lively campus, UMass Amherst is 16 miles from Chesterfield. Experience the city's energetic vibe, diverse dining options, and exciting events that showcase student life.
  • Chesterfield Gorge: Nestled within Chesterfield, this picturesque gorge offers thrilling outdoor adventures, scenic vistas, and hiking trails. Enjoy nature's beauty and serene environment while exploring this local gem.

Things to do recommended for couples

For a romantic getaway in Chesterfield, consider an enchanting evening at Jacob's Pillow for dance performances, hitting the slopes at Blandford Ski Area for some fun together, or indulging in a soothing experience at Elements Hot Tub Spa to unwind and reconnect. Enjoy your couple's retreat.

Things to do recommended for families

Your family vacation in Chesterfield promises exciting experiences. Enjoy wellness at Land of Providence, unleash your competitive spirit at Mullins Center, or have a blast at Spare Time Bowling, where adventure awaits. Each location offers a unique atmosphere perfect for family bonding and fun.

Things to do recommended for groups

Your group can enjoy a cultural evening at the Academy of Music Theater, just 12 miles away, followed by an adventurous hike on the Skyline Trail, 10 miles from Chesterfield. Don’t miss the unique offerings at the Montague Bookmill, located 14 miles away, for a charming local experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Chesterfield

If you're planning a trip with friends, family, or pets, or if you're considering an extended stay, be sure to use the appropriate filters to match your preferences. Here are some helpful booking tips for Vrbo.

  • Traveling to Chesterfield with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Chesterfield with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chesterfield: For many, a family vacation wouldn’t feel complete without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chesterfield: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can easily discover and save on monthly accommodations. Don't forget to consider including features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Chesterfield

Chesterfield, Massachusetts, is a hidden gem for outdoor enthusiasts and adventure seekers alike. Surrounded by picturesque landscapes, you’ll find breathtaking views and ample outdoor spaces perfect for family-friendly activities. Explore nearby towns in New Hampshire for a relaxing atmosphere, friendly locals, and charming neighborhoods. Whether you’re hiking scenic trails or simply soaking in the beauty, Chesterfield offers a delightful blend of adventure and tranquility for an unforgettable getaway.

  • Northampton: Northampton is a vibrant city located 11 miles from Chesterfield, known for its rich cultural scene and outdoor activities. Visitors are drawn to its eclectic mix of historic and modern colleges, offering a unique educational atmosphere. The city is home to numerous music concerts and festivals, making it a cultural hub in the region. Enjoy the beautiful lakes nearby, perfect for a leisurely day of boating or picnicking. With a variety of shops, restaurants, and galleries, Northampton provides a lively urban experience intertwined with the charm of New England.
  • Western Massachusetts: Just 2 miles away from Chesterfield, Western Massachusetts is a paradise for outdoor enthusiasts and adventure seekers. This region boasts stunning scenery, featuring majestic mountains and serene lakes, ideal for hiking, skiing, and exploring. The area is dotted with ski resorts, offering winter sports activities to thrill-seekers. Nature lovers can revel in the beauty of the nearby national state parks, perfect for camping and wildlife watching. Whether you're looking for an adrenaline rush or a peaceful retreat, Western Massachusetts has something for everyone.
  • Goshen: Located 4 miles from Chesterfield, Goshen is a charming town that invites visitors to enjoy its romantic ambiance and breathtaking scenery. Surrounded by nature, the town's recreational areas and resorts provide the ideal backdrop for relaxation and adventure. Art enthusiasts will appreciate the local galleries showcasing unique works. Explore the nearby national state park for hiking and scenic views, or spend a quiet afternoon by the lake. Goshen’s combination of outdoor beauty and cultural experiences makes it a lovely destination for couples and families alike.

Best time to go to Chesterfield

If you're planning a trip to Chesterfield, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March to April and July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.9°F (-3.4°C)Light RainMostly SunnyLowSlightly High
February27.3°F (-2.6°C)Light RainMostly SunnyAverageSlightly High
March35.2°F (1.8°C)Light RainMostly SunnyHighAverage
April47.1°F (8.4°C)Light RainMostly SunnyHighSlightly Low
May58.6°F (14.8°C)Light RainMostly SunnyAverageAverage
June66.6°F (19.2°C)Light RainMostly SunnyAverageAverage
July72.7°F (22.6°C)Light RainMostly SunnyHighAverage
August70.9°F (21.6°C)Light RainMostly SunnyAverageAverage
September63.7°F (17.6°C)Light RainMostly SunnyAverageSlightly Low
October52.3°F (11.3°C)Light RainMostly SunnyAverageSlightly Low
November40.3°F (4.6°C)Light RainMostly SunnyLowAverage
December32.0°F (0.0°C)Light RainMostly SunnyLowSlightly High

Booking with Vrbo is simple

Are you interested in saving money on your upcoming trip? Being flexible with your travel dates can really help, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your travel needs.

Save more with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash on qualifying reservations. Sign up today and start enjoying the savings.

Vrbo Trips: Planning made easy

Vrbo's Trip Board is a valuable tool that allows you to plan your journeys effortlessly. You can start new trips, pick up right where you left off, or easily view and arrange your travel plans. Any properties you've saved or booked in the past are conveniently located under Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Travel to adventurous Chesterfield

The parks and surrounding scenery provide a peaceful ambiance to your vacation 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 find top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Chesterfield a one-of-a-kind vacation spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Blandford Ski Area (14.1 mi / 22.7 km)
  • Bas Ridge Golf Course (14.8 mi / 23.8 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 looking for fun outdoor activities or just want to appreciate the scenery, Chesterfield is a great place to get outside. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Chesterfield Gorge (2.1 mi / 3.4 km)
  • Pine Island (5 mi / 8 km)
  • Look Memorial Park (8.4 mi / 13.5 km)
  • Paradise Pond (11.3 mi / 18.2 km)
  • Smith College Botanic Garden (11.3 mi / 18.3 km)
  • Nashawannuck Pond (12.7 mi / 20.5 km)

Traveling to and around Chesterfield

Fly into Westfield, MA (BAF-Barnes Municipal), the closest airport, located 16.6 mi (26.8 km) from the city center. If you can't find a flight that works for your travel itinerary, 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, Massachusetts, United States of America when booking a vacation rental?
When considering a vacation rental in Chesterfield, Massachusetts, the area around the scenic hills and tranquil landscapes is particularly appealing. This region offers a peaceful retreat, great for those looking to unwind in nature. Not far from here, you can explore the picturesque Mount Tom State Reservation, which provides stunning views, hiking trails, and opportunities for outdoor activities. Additionally, the charming local culture can be experienced at nearby small-town shops and eateries that reflect the unique character of the area.

Chesterfield features a variety of properties, ranging from cozy cabins to larger homes, allowing visitors to find accommodations that suit their needs.
How much does it cost to rent a vacation home in Chesterfield?
Prices for vacation 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 vacation 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 ski resort rentals near Chesterfield, travelers should consider the nearby town of Williamsburg, which provides convenient access to the slopes of the Berkshire Mountains. The area features a variety of accommodations, including cozy cabins and lodges that cater to winter sports enthusiasts. Many properties in this region come with amenities such as fireplaces, hot tubs, and spacious living areas, great for unwinding after a day of skiing.

In addition, the surrounding towns of Ashfield and Cummington offer charming rural homes that can serve as tranquil retreats. These residences often include features like fully equipped kitchens, outdoor decks, and scenic views of the surrounding landscape. Staying in these areas not only provides proximity to skiing but also access to local shops and restaurants, enhancing the overall experience for visitors.

For those looking to explore beyond the ski slopes, the region boasts numerous hiking trails and natural attractions, allowing for a well-rounded winter getaway.
What is the most popular type of vacation rental accomodation in Chesterfield?
In Chesterfield, cabins are the most popular type of vacation rental, with several available throughout the area. These cabins typically provide a rustic charm and a cozy atmosphere, often featuring amenities such as fully equipped kitchens, comfortable living spaces, and outdoor decks or patios that allow guests to enjoy the natural surroundings. Many are situated near scenic spots for hiking and exploring the beautiful landscapes of western Massachusetts, making them ideal for travelers seeking a peaceful retreat.
Can I find long-stay vacation rentals in Chesterfield?
A long-stay vacation rental in Chesterfield is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Chesterfield vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chesterfield with parking available—perfect for families or travelers 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 vacation rental amenities include decks or patios, which provide guests with a private outdoor space to relax and enjoy the natural surroundings. Most rentals also feature fully equipped kitchens, allowing travelers to prepare their own meals during their stay. Additionally, many properties come with coffee and tea makers, superb for starting the day with a warm beverage. Dining areas are commonly included, accommodating family meals or gatherings. For those who enjoy the outdoors, rentals often highlight nearby hiking locations, making it easy for guests to explore the beautiful landscapes of the area.
When is the best time to visit Chesterfield for a vacation rental?
April is the most popular month to visit Chesterfield, as it marks the heart of the peak season running from March to May. This time of year draws travelers eager to experience the area's beautiful landscapes and outdoor activities. As spring blooms, visitors can enjoy hiking trails, birdwatching, and the vibrant colors of wildflowers, all while basking in temperatures ranging from the low 40s to mid-60s Fahrenheit.

The pleasant weather in April creates an inclusive setting for outdoor exploration, making it an ideal time to take leisurely strolls through local parks or engage with the surrounding natural beauty. Chesterfield's charming small-town vibe, combined with its outdoor offerings, ensures that you'll find plenty to see and do.

For those looking for a more budget-friendly option, consider visiting in January. While it may be the low season, this month offers its own great experiences, such as winter hikes and cozy gatherings in the local community.

Ultimately, your choice of when to visit Chesterfield should reflect your desire for vibrant spring activities or a quiet winter retreat.
How early should I book a Chesterfield vacation rental?
Book your Chesterfield vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chesterfield, Massachusetts, United States of America?
In Chesterfield, Massachusetts, visitors can enjoy the serene beauty of the Berkshires, with numerous outdoor attractions to explore. The town's picturesque landscapes make it a great destination for hiking and nature enthusiasts, particularly in the nearby Mount Tom State Reservation, which offers scenic trails and stunning views.

The historic Chesterfield Gorge, part of the Trustees of Reservations, is a must-see for its striking rock formations and beautiful river views. For those interested in local culture, the area hosts a variety of seasonal festivals and farmers' markets, showcasing regional crafts and produce.
Can I change or cancel my Chesterfield home rental booking on Vrbo?
To find Chesterfield vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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