Pittsfield vacation rentals

We found 1,020 vacation rentals — enter your dates for availability

Discover a selection of 39 homes and other vacation rentals in Pittsfield that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation homes have the amenities you expect for your stay, including WiFi and parking. No matter what you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Pittsfield

Showing deals for:May 29 - Jun 5

Image gallery for Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Property grounds
10 out of 10, Exceptional, (64 reviews)
Exceptional
(64 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
Price is $738
$5,165 for 7 nights
All fees included
Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Pittsfield

Why visit Pittsfield

  • Outdoor Adventures: Pittsfield is perfect for skiing and various outdoor sports, making it an adventure lover's paradise.
  • Rich History: Explore historic houses and landmarks that showcase the city's charming past.
  • Scenic Beauty: Enjoy the stunning landscapes of the Berkshires, ideal for nature enthusiasts and photographers.
  • Family-Friendly Atmosphere: The neighborhoods offer a welcoming environment for families, couples, and budget travelers alike.
  • Diverse Accommodations: Choose from cozy vacation rentals, modern condos, and charming cottages to enhance your stay.

Popular types of accommodation in Pittsfield

Planning a getaway to Pittsfield? Discover the perfect place to stay with our selection of vacation rentals. From cozy houses and modern condos to charming cottages, there’s something for everyone. Many options feature spacious layouts, including bedroom apartments with ample parking and even spacious basements for extra comfort. Make your stay memorable by choosing the ideal rental that fits your needs in this beautiful destination.

  • Houses: The top choice for travelers to Pittsfield, these homes offer a spacious and comfortable setting for families and friends.
  • Condos: A popular second option, condos provide modern amenities and often stunning views, perfect for a relaxing getaway.
  • Cottages: These charming retreats, ranked third, offer a cozy atmosphere ideal for romantic escapes or peaceful weekends.
  • Apartments: Fourth on the list, apartments are a convenient choice for those seeking a home-like feel in the city.
  • Cabins: Rounding out the options, cabins present a rustic ambiance, perfect for nature enthusiasts looking for adventure.**

Top attractions in and around Pittsfield

Pittsfield, Massachusetts, is an excellent destination for ski and adventure enthusiasts, offering a variety of sports vacation opportunities. Visitors can explore historic houses, scenic reserves, and majestic mountains, making it ideal for those seeking cultural and outdoor adventures. With its diverse attractions, Pittsfield promises a memorable experience for travelers looking to immerse themselves in nature and history.

  • Hancock Shaker Village: Step back in time at this living history museum showcasing the unique lifestyle and craftsmanship of the Shakers. Explore beautifully restored buildings, lush gardens, and engaging exhibits that highlight their communal way of life and innovative agricultural practices.
  • National Shrine of the Divine Mercy: A peaceful retreat and spiritual haven, this shrine features stunning architecture, serene gardens, and beautiful sculptures. Visitors can participate in mass, prayer services, and enjoy the tranquil atmosphere.
  • The Mount: The former home of author Edith Wharton, this historic estate offers guided tours through its elegant gardens and beautifully preserved interiors, reflecting Wharton's literary legacy and her love for architecture and design.

Things to do recommended for couples

Looking for a romantic getaway in Pittsfield? Enjoy skiing together at Jiminy Peak Mountain Resort or Bousquet Ski Area, both offering thrilling sports vibes. For a more relaxed experience, savor a wine tasting at Furnace Brook Winery at Hilltop Orchards, where romance and entertainment await.

Things to do recommended for families

Your family vacation in Pittsfield promises memorable experiences. Explore the wellness vibes at Kennedy Park and Shatford Memorial Park, both 5 and 7 miles away, respectively. For thrills, don’t miss the Alpine Super Slide, located 7 miles from downtown Pittsfield, offering excitement for all ages.

Things to do recommended for groups

Experience the vibrant arts at the Colonial Theater, enjoy a round of golf at the Skyline Country Club just 4 miles away, and explore local flavors at Guido's Marketplace. These activities offer a perfect mix of culture, outdoor fun, and community vibes for your group.

*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 Pittsfield

No matter if you're traveling with friends, family, pets, or planning an extended getaway, it's important to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Pittsfield with a group: Think about how many bedrooms you'll require and any additional features you might want, like a full kitchen or outdoor area for group gatherings. Thankfully, on Vrbo, you can easily filter for all these options and more.
  • Traveling to Pittsfield with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with offering suitable amenities like a private pool. Additionally, you might want to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Pittsfield: For many families, a vacation isn’t truly complete without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Pittsfield: If you're in search of vacation rentals with discounts for extended stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Pittsfield

Pittsfield, Massachusetts, offers a unique blend of historical charm and outdoor adventure perfect for every traveler. Enjoy skiing, sports, and the beautiful scenery that surrounds this vibrant city. Nearby neighborhoods provide a family-friendly atmosphere, romantic spots, and budget-friendly options for accommodations. Whether you're seeking a vacation rental or a relaxing retreat, Pittsfield serves as a great base for exploring the Berkshires and its many attractions.

  • Lenox: Lenox is a charming city located 7 miles from Pittsfield, known for its vibrant cultural scene and picturesque landscapes. This destination offers a delightful mix of entertainment, romance, and family-friendly activities. Visitors can enjoy music concerts and theatrical performances, as well as outdoor adventures like skiing in the winter months. With its stunning lakes and nearby mountains, Lenox is perfect for those who appreciate natural beauty. Additionally, Lenox features a variety of event venues that host conferences and gatherings, making it a great spot for both leisure and business travel.
  • Lee: Situated 10 miles away from Pittsfield, Lee is a quaint city that attracts travelers looking for a romantic getaway, family adventures, and entertainment options. The city boasts a vibrant theater scene and hosts numerous music concerts throughout the year. Outdoor enthusiasts will appreciate the nearby ski fields and recreational opportunities in the surrounding mountains and lakes. Lee is also home to several historical monuments, allowing visitors to explore its rich heritage while enjoying the warm, welcoming atmosphere of this charming town.
  • Stockbridge: Located 12 miles from Pittsfield, Stockbridge is a cultural gem that offers a unique blend of artistic experiences and romantic settings. Known for its rich history and vibrant arts scene, Stockbridge features a variety of music concerts, theater productions, and ski fields for outdoor fun. Key attractions include beautiful lakes, historical monuments, and serene shrines that provide a peaceful escape. Stockbridge's enchanting atmosphere and cultural offerings make it a must-visit destination for those seeking memorable experiences in the Berkshires.

Best time to go to Pittsfield

If you're planning a trip to Pittsfield, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.6°F (-5.2°C)Light RainMostly CloudyAverageAverage
February24.6°F (-4.1°C)Light RainMostly CloudyAverageAverage
March32.4°F (0.2°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May56.3°F (13.5°C)Light RainMostly SunnyAverageAverage
June64.0°F (17.8°C)Light RainMostly SunnySlightly HighAverage
July70.3°F (21.3°C)Light RainMostly SunnySlightly HighSlightly High
August68.4°F (20.2°C)Light RainMostly SunnySlightly HighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnyAverageAverage
October50.0°F (10.0°C)Light RainMostly SunnySlightly LowSlightly Low
November37.6°F (3.1°C)Light RainMostly SunnySlightly LowAverage
December29.3°F (-1.5°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire reservation. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you’ll gain access to exclusive discounts and accumulate OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board feature offers you a convenient place to plan new trips, pick up right where you left off, and manage your travel arrangements. You can easily find the properties you’ve saved and booked in the Potential, Upcoming, or Current Trips sections. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore the lakeside setting in Pittsfield

Take a vacation to Pittsfield and enjoy the area's entertainment, theater scene and opera. This city's baseball games, museums and biking draw many visitors. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Pittsfield

Do you want to find attractions to see while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Pittsfield a fun place to get away. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Bousquet Ski Area (2.6 mi / 4.3 km)
  • Wyndhurst Golf & Club (7.3 mi / 11.8 km)
  • Jiminy Peak Mountain Resort (7.6 mi / 12.3 km)
  • Otis Ridge (19.2 mi / 30.8 km)
  • Hudson Chatham Winery (21.9 mi / 35.3 km)
  • Kennedy Park (4.9 mi / 7.9 km)

Exploring the natural landscape of Pittsfield

Whether you're looking for adventure or just want to appreciate the scenery, Pittsfield is a great place to get outside. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Mount Greylock State Reservation Visitor Center (7.6 mi / 12.2 km)
  • The Mount (7.9 mi / 12.8 km)
  • Stockbridge Bowl (8.5 mi / 13.7 km)
  • Queechy Lake (8.7 mi / 14 km)
  • Berkshire Botanical Garden (11 mi / 17.8 km)
  • Naumkeag Museum (11.4 mi / 18.4 km)

Transportation options to and around Pittsfield

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 2.5 mi (4 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away.

If you'd rather travel by train, make your way to Pittsfield Intermodal Transportation Center or Pittsfield Station to see more of the city.

Frequently asked questions

What is the best area to stay in Pittsfield, Massachusetts, United States of America when booking a vacation rental?
When considering a vacation rental in Pittsfield, Massachusetts, one of the best areas to explore is the downtown district. This vibrant neighborhood is not only the heart of the city but also offers a delightful mix of dining, shopping, and cultural experiences. You can easily access attractions such as the Berkshire Museum, which showcases the region's art, history, and natural science, or enjoy a performance at the historic Colonial Theatre, known for its beautiful architecture and diverse lineup of shows.

Another appealing area is the outskirts of Pittsfield, particularly near the scenic Pittsfield State Forest. This region is superb for nature lovers, offering numerous outdoor activities like hiking, biking, and birdwatching. The serene environment makes it an ideal spot for those looking to unwind and appreciate the natural beauty of the Berkshires.

In terms of vacation rentals, downtown typically features a variety of properties, from charming apartments to more spacious homes, making it suitable for different group sizes and preferences.
How much does it cost to rent a vacation home in Pittsfield?
Prices for vacation rentals in Pittsfield 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 Pittsfield 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 Pittsfield vacation house rentals?
You can find great discounts on house rentals in Pittsfield 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 Pittsfield ski resort rentals?
For ski resort rentals near Pittsfield, Massachusetts, travelers should consider the nearby Jiminy Peak Mountain Resort, located just a short drive away. In the town of Hancock, close to the resort, there are a variety of vacation rentals available, including cozy cabins and chalets that cater to both couples and families. Many of these properties offer amenities such as wood-burning stoves, spacious living areas, and fully equipped kitchens, allowing guests to enjoy a comfortable stay after a day on the slopes.

Additionally, the towns of Lenox and Stockbridge, which are also conveniently located for accessing Jiminy Peak, feature charming inns and vacation homes that often showcase classic New England architecture. These accommodations may include amenities like hot tubs, outdoor patios, and proximity to local dining options. The tranquil surroundings of the Berkshires make for an inviting retreat, with many rentals providing scenic views of the snow-covered landscape.

For those looking to explore beyond skiing, the region offers a wealth of cultural attractions, including the nearby Tanglewood Music Center and the Norman Rockwell Museum. Rentals in this area often allow for easy access to both winter sports and cultural experiences, making it an ideal destination for those who want to combine outdoor fun with local heritage. See all ski-in-/ski-out rentals in Pittsfield.
What is the most popular type of vacation rental accomodation in Pittsfield?
In Pittsfield, vacation houses are the most popular type of rental, with about 34 available throughout the area. These houses often come with multiple bedrooms, fully equipped kitchens, and spacious living areas, providing a comfortable home base for families or groups. Many also feature outdoor spaces such as decks or gardens, great for enjoying the scenic surroundings. Additionally, there are several apartments, cottages, and condos available, offering a variety of options for travelers seeking different experiences.
Are there any family house rentals in Pittsfield?
In Pittsfield, Massachusetts, there are numerous family-friendly house rentals available, with about 32 options to choose from. This charming city is surrounded by stunning natural beauty, making it an excellent destination for families. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces superb for children to play.

Travelers will find that properties in neighborhoods close to Burbank Park provide easy access to playgrounds, walking trails, and picnic areas, allowing for fun-filled outdoor activities. Additionally, homes near the downtown area often feature amenities like Wi-Fi and air conditioning, ensuring a comfortable stay for everyone.
Can I rent a vacation home with a pool or hot tub in Pittsfield?
In Pittsfield, there are several vacation homes available for rent that feature pools and hot tubs, making it an appealing destination for travelers seeking relaxation and leisure. The area offers a mix of properties, including charming cottages and spacious family homes, often equipped with amenities such as private pools, outdoor patios, and hot tubs for unwinding after a day of exploring. Many rentals also come with fully equipped kitchens and comfortable living spaces, ensuring a pleasant stay.
Can I find long-stay vacation rentals in Pittsfield?
A long-stay vacation rental in Pittsfield 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 pet-friendly house rentals in Pittsfield?
In Pittsfield, travelers can find a variety of pet-friendly house rentals, with around 20 options available. Many of these properties offer inviting amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, making them ideal for families or groups traveling with pets.

The neighborhood is surrounded by beautiful parks, including the popular Pittsfield State Forest, which provides ample opportunities for hiking and outdoor activities. This forest is a fantastic spot for pet owners to enjoy nature walks with their furry friends, thanks to its scenic trails and open spaces. Additionally, the nearby Bousquet Mountain offers recreational opportunities in both summer and winter, enhancing the area's appeal for outdoor enthusiasts. See all pet-friendly rentals in Pittsfield.
Are there any remote work vacation rentals in Pittsfield?
In Pittsfield, Massachusetts, there are numerous options for remote work vacation rentals, with around 44 properties available. These rentals cater well to those needing a productive environment while enjoying their stay. Travelers can expect amenities such as dedicated workspaces with desks and chairs, high-speed internet access, and free Wi-Fi, allowing for a seamless work-from-home experience.

The city itself is rich in culture and history, with nearby attractions like the Berkshire Museum and the scenic Pittsfield State Forest offering opportunities for relaxation after a day of work. Additionally, the area is well-known for its beautiful parks and outdoor activities, making it an ideal destination for those looking to balance work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pittsfield vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Pittsfield 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 Pittsfield?
In Pittsfield, popular vacation rental amenities include fully equipped kitchens, providing travelers the convenience of preparing their own meals. Many rentals also feature cozy fireplaces, superb for warming up during the cooler months. Onsite parking is commonly available, making it easy for guests to explore the surrounding area. Additionally, rentals often come with coffee and tea makers, offering a comfortable start to the day. Many properties also provide outdoor spaces such as decks or patios, allowing guests to enjoy the fresh air and local scenery.
When is the best time to visit Pittsfield for a vacation rental?
The peak travel season in Pittsfield spans from June to August, with July being the most popular month for visitors. This summer period is superb for those seeking outdoor adventures, as the warm weather invites a variety of activities such as hiking, biking, and exploring the beautiful landscapes of the Berkshires. Travelers can enjoy nearby attractions like Tanglewood, the summer home of the Boston Symphony Orchestra, where music fills the air against a picturesque backdrop.

During these months, expect temperatures to range from the low 50s to the high 80s Fahrenheit, providing a comfortable environment for sightseeing. The vibrant setting in July draws many fellow travelers, creating a lively scene filled with festivals and events, making it an excellent time for those who thrive in social settings.

For those looking for a more budget-friendly option, consider visiting Pittsfield in December, when the area transforms into a winter wonderland. Although this is a quieter time, it offers great experiences like holiday festivities and the beauty of snow-covered landscapes, superb for a cozy getaway.

Ultimately, the best time to visit Pittsfield depends on your preference for bustling summer activities or a tranquil winter escape.
How early should I book a Pittsfield vacation rental?
Book your Pittsfield 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 Pittsfield, Massachusetts, United States of America?
In Pittsfield, Massachusetts, visitors can explore a variety of attractions that highlight the area's natural beauty and cultural heritage. The Berkshire Museum, located in the downtown area, features art, science, and history exhibits, making it a great spot for families and art enthusiasts alike. Nearby, the historic District of Pittsfield offers charming architecture and local shops, great for a leisurely stroll.

For outdoor enthusiasts, the scenic Burbank Park on Onota Lake provides opportunities for fishing, boating, and picnicking, surrounded by picturesque views. The nearby Pittsfield State Forest offers hiking trails and opportunities for winter sports, making it a year-round destination for nature lovers.
Can I change or cancel my Pittsfield home rental booking on Vrbo?
To find Pittsfield 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 Pittsfield 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.

More Vacation Ideas