Pittsfield vacation rentals

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.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	22.6°F (-5.2°C)	Light Rain	Mostly Cloudy	Average	Average
February	24.6°F (-4.1°C)	Light Rain	Mostly Cloudy	Average	Average
March	32.4°F (0.2°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	44.2°F (6.8°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
May	56.3°F (13.5°C)	Light Rain	Mostly Sunny	Average	Average
June	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	70.3°F (21.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	68.4°F (20.2°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
September	61.3°F (16.3°C)	Light Rain	Mostly Sunny	Average	Average
October	50.0°F (10.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
November	37.6°F (3.1°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	29.3°F (-1.5°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly 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.

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)
• Ski Butternut (18.7 mi / 30 km)
• Otis Ridge (19.2 mi / 30.8 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)
• Wahconah Falls State Park (7.6 mi / 12.3 km)
• The Mount (7.9 mi / 12.8 km)
• Stockbridge Bowl (8.5 mi / 13.7 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.