Pittsfield vacation rentals

We found 1,002 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:Mar 27 - Apr 3

Image gallery for Waterfront Cottage 10 Min From Great Barrington

Property grounds
10 out of 10, Exceptional, (99 reviews)
Exceptional
(99 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
Price is $328
$2,297 for 7 nights
All fees included
Waterfront Cottage 10 Min From Great Barrington

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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)
  • Kennedy Park (4.9 mi / 7.9 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)
  • Pineridge Cross Country Ski Center (19.9 mi / 32.1 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:

  • Lenox Mountain (4.2 mi / 6.8 km)
  • Kennedy Park (4.9 mi / 7.9 km)
  • 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)

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 when booking a vacation rental?
When planning a vacation in Pittsfield, Massachusetts, one of the best areas to consider is the historic downtown district. This vibrant area is not only rich in cultural heritage but also offers a variety of vacation rental options, with numerous properties available that cater to different tastes and budgets. Staying downtown puts you within walking distance of attractions such as the Berkshire Museum, where you can explore art, history, and science exhibits, and the historic Colonial Theatre, which hosts a variety of performances and events throughout the year.

Another great option is the Springside Park neighborhood, which offers a more tranquil setting while still being close to the city's amenities. This area features beautiful natural surroundings and is great for those who enjoy outdoor activities. The park itself is a lovely spot for hiking, picnicking, and enjoying the scenic landscapes, making it a peaceful retreat after a day of exploration.

Both neighborhoods provide a unique blend of convenience and charm, ensuring a memorable stay in Pittsfield.
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, the closest ski area is Jiminy Peak, located about 30 minutes away. Travelers seeking accommodations in this region may want to consider the nearby towns of Hancock and Lanesborough. In Hancock, you can find cozy chalets and cabins that cater to families and groups, often featuring amenities like wood-burning stoves, fully equipped kitchens, and outdoor spaces for enjoying the fresh mountain air.

In Lanesborough, vacation rentals may offer a more rustic experience, with properties set against the backdrop of nature, ideal for those looking to unwind after a day on the slopes. Many homes here come with comfortable living areas, game rooms, and access to scenic views. Some rentals might also include additional perks such as fire pits or hot tubs, great for relaxing in the evenings.

Furthermore, the area around Pittsfield is rich in natural beauty, with access to hiking trails and local attractions like the Berkshire Museum and the historic downtown. This makes the region not only a great spot for skiing but also a wonderful place to explore year-round.
What is the most popular type of vacation rental accomodation in Pittsfield?
In Pittsfield, vacation houses are the most popular rental option, with around 30 available throughout the area. These houses typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or larger groups. Many properties also include outdoor spaces like decks or gardens, great for enjoying the scenic views of the Berkshires.

Additionally, there are several cottages, apartments, condos, and cabins offered, each providing unique amenities. Cottages may come with rustic charm and proximity to natural settings, while condos often feature modern conveniences and community amenities like pools or fitness centers.
Are there any family house rentals in Pittsfield?
In Pittsfield, Massachusetts, there are numerous family-friendly house rentals available—around 32 in total. This charming city offers a variety of accommodations suitable for families, particularly in neighborhoods like the historic downtown area and the scenic Berkshire Hills. Many of these homes come equipped with spacious living areas, fully stocked kitchens for preparing family meals, and outdoor spaces superb for children to play or for hosting barbecues.

Visitors to Pittsfield can enjoy proximity to local attractions such as the Berkshire Museum and the Edith Wharton Home, both of which provide enriching experiences for all ages. The nearby parks, including Burbank Park and Pittsfield State Forest, offer ample opportunities for outdoor activities such as hiking and picnicking. See all family-friendly rentals in Pittsfield.
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 or hot tubs, providing a fantastic option for travelers looking to enjoy a relaxing getaway. The area offers a mix of charming neighborhoods, including residential zones with easy access to parks and recreational activities.

Rentals in Pittsfield typically come equipped with amenities such as private pools, hot tubs, spacious outdoor areas, and fully equipped kitchens, ideal for families or groups wanting to unwind and entertain. Travelers can also explore the nearby Berkshire Mountains, known for their scenic beauty and outdoor activities, making it easy to blend relaxation with adventure during their stay. Find your rental in Pittsfield with a pool or a hot tub.
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, there are a variety of pet-friendly house rentals available, with around 21 options to choose from. Travelers can expect amenities such as spacious yards, well-equipped kitchens, and cozy living areas, great for families or groups. Many of these rentals are located in residential neighborhoods, providing a peaceful atmosphere while still being close to local attractions.

For those traveling with pets, the area is near several parks and green spaces, including Burbank Park and the picturesque Onota Lake, which offer walking trails and open areas for pets to enjoy. Additionally, the nearby Pittsfield State Forest provides scenic hiking opportunities, allowing for outdoor adventures with furry companions. 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 45 available across the area. Travelers can expect accommodations that are well-equipped for productivity, featuring amenities such as high-speed Wi-Fi, dedicated office spaces, desks, ergonomic chairs, and even computer monitors in some properties.

The downtown area of Pittsfield offers convenient access to local coffee shops and restaurants, superb for a change of scenery during work breaks. Additionally, the proximity to attractions like the Berkshire Museum and the scenic parks in the region provides excellent opportunities for leisure and relaxation after a day of remote work. 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, allowing guests to prepare their own meals. Many rentals also feature WiFi, which is essential for staying connected during your visit. Travelers can expect additional conveniences such as blenders for making smoothies or soups, coffee and tea makers for a cozy start to the day, and patios that provide outdoor space for relaxation or enjoying a meal al fresco.
When is the best time to visit Pittsfield for a vacation rental?
The best time to visit Pittsfield for a vacation rental is during the summer months, particularly in July, when the area comes alive with vibrant culture and outdoor activities. This peak season, spanning from June through August, offers warm temperatures—typically in the mid-70s to low 80s Fahrenheit—superb for exploring the beautiful parks and engaging in a variety of recreational pursuits.

Visitors can enjoy the scenic wonders of the Berkshires, with opportunities for hiking, kayaking, and visiting local festivals that celebrate the region's rich arts scene. July is especially lively, with a range of events and activities that draw both locals and tourists, making it an ideal time for those seeking a vibrant atmosphere.

If you prefer a quieter experience, consider visiting Pittsfield in December. While this is a low season, it provides a cozy charm, offering a chance to explore the town adorned in festive decorations.
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?
In Pittsfield, visitors can enjoy a range of attractions that showcase the area's rich history and natural beauty. The downtown area features the Berkshire Museum, which offers a mix of art, science, and history exhibits, along with the nearby Colonial Theatre, known for its live performances and historic architecture.

For outdoor enthusiasts, Pittsfield State Forest provides numerous hiking trails, picnic areas, and opportunities for birdwatching, making it a great spot to connect with nature. The nearby Bousquet Mountain offers seasonal activities, including skiing in the winter and mountain biking in the warmer months.

Additionally, the area around Lake Onota is great for those looking to enjoy water activities, with options for swimming, kayaking, and enjoying scenic walks along the shore.
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.

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