Pittsfield Vacation Rentals, Massachusetts: house rentals & more

Discover a selection of 36 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.

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Bousquet Ski Area

Find the best place to stay - Pittsfield

Great Room with pull out doble sleeper sofa that sleeps 2

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Sleeps 28 · 8 bedrooms · 3 bathrooms

Top rated rentals - Pittsfield

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Find out more about Pittsfield

Why visit Pittsfield

Outdoor Adventure: Pittsfield State Forest offers excellent skiing and outdoor activities, perfect for adventure seekers.
Rich History: Explore the city’s historic houses and learn about its cultural heritage.
Scenic Landscapes: Enjoy captivating natural scenery that enhances the city’s charm and tranquility.
Family-Friendly Atmosphere: Pittsfield features neighbourhoods suitable for families and couples, making it a serene getaway.
Diverse Accommodations: Choose from a variety of vacation rentals, including homes, cottages, and condos to fit your needs.

Popular types of accommodation in Pittsfield

Explore the charm of Pittsfield with our selection of vacation rentals. Whether you prefer a private vacation home, a cozy cottage, or a modern condo, we have the perfect accommodation to suit your needs. Our platform offers a variety of options, including apartments in Pittsfield, ensuring you find a space that fits your group and itinerary. Discover your ideal getaway in this beautiful Canadian destination today!

Houses: The top choice for visitors in Pittsfield, ideal for families or groups seeking spacious and comfortable accommodations.
Condos: A popular option among travellers looking for modern amenities and convenient locations in the heart of the city.
Cottages: Charming and often nestled in nature, cottages provide a cozy retreat for those wanting a rustic experience.
Apartments: A practical choice for solo travellers or couples, offering the comforts of home during your stay.
Cabins: Perfect for outdoor enthusiasts, cabins offer a unique and tranquil escape in the beautiful surroundings of Pittsfield.**

Top attractions in Pittsfield

Pittsfield, Massachusetts, is ideal for skiing, adventure, and sports vacations. It boasts a variety of attractions, including historic houses, nature preserves, and mountains, making it a great destination for travellers seeking culture and outdoor experiences. Whether you're exploring the stunning landscapes or delving into local history, Pittsfield offers something for everyone, ensuring an unforgettable getaway.

Hancock Shaker Village: This historic village immerses you in Shaker culture, showcasing beautifully restored buildings, traditional craftsmanship, and serene gardens. Experience the unique lifestyle of the Shakers through engaging exhibits and demonstrations.
National Shrine of the Divine Mercy: Located 17.7km from Pittsfield, this serene shrine offers a peaceful retreat for reflection and prayer. Its stunning architecture and beautiful grounds provide a tranquil atmosphere, highlighting the importance of divine mercy.
Berkshire Museum: Situated in Pittsfield, this family-friendly museum features natural history exhibits, art collections, and interactive displays. It's an enriching experience for all ages, combining culture and education in a welcoming environment.

Things to do recommended for couples

For a romantic getaway in Pittsfield, enjoy a concert at Tanglewood Music Center, just 11.3km away. Embrace winter fun at Jiminy Peak Mountain Resort, 12.9km out, or indulge in wine tasting at Furnace Brook Winery, also 12.9km away, perfect for a cozy, romantic evening.

Things to do recommended for families

Families visiting Pittsfield will love the serenity of Kennedy Park and Shatford Memorial Park, both offering relaxation and outdoor fun just 5 and 11.3km away, respectively. For a thrill, the Alpine Super Slide, located 11.3km away, promises exciting amusement for all ages.

Things to do recommended for groups

Groups visiting Pittsfield can enjoy a captivating performance at the Colonial Theater, unwind with a round of golf at the Skyline Country Club, and explore local flavours at Guido's Marketplace, immersing themselves in the vibrant community atmosphere.

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

If you're travelling with a group, with family, bringing your pets, or seeking extended stays, it's important to prioritise your filters accordingly. Here are some helpful Vrbo booking tips for you.

Traveling to Pittsfield with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
Traveling to Pittsfield with young kids: Traveling with young children can present certain challenges. It's important to prioritize their comfort and safety, along with ensuring access to age-appropriate amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is a wise choice.
Taking your pets with you to Pittsfield: For many families, a trip wouldn't feel complete without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
Planning for a long term stay visiting Pittsfield: If you're in search of vacation rentals with discounts for 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 options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Pittsfield

Pittsfield, Massachusetts, offers an enchanting blend of adventure and relaxation for Canadian travellers. Explore the stunning natural landscapes of Pittsfield State Forest, perfect for skiing and outdoor activities. The city's historical charm is complemented by nearby family-friendly and romantic neighbourhoods, providing a serene atmosphere for all budgets. Don't miss out on the captivating scenery that surrounds this charming city, making Pittsfield an ideal vacation spot to unwind and explore.

Lenox: Located 11.3km from Pittsfield, Lenox is a charming town known for its vibrant entertainment scene and romantic ambiance. Visitors flock to Lenox for its music concerts and theatrical performances, making it a great spot for a family outing or a couple's getaway. The area is surrounded by stunning natural beauty, including serene lakes and majestic mountains. Notable attractions include cultural venues that host events and conferences, providing a perfect blend of leisure and culture.
Stockbridge: Situated 19.3km from Pittsfield, Stockbridge is a picturesque town that offers a rich cultural experience. This charming locale is celebrated for its romantic settings, making it a beloved destination for couples. Visitors can enjoy live music and performances at local theatres, along with exploring the scenic ski fields. Don't miss the chance to visit significant landmarks such as serene lakes, historical monuments, and the iconic shrine that reflect the town's rich heritage and artistic spirit.
Hancock: Just 11.3km from Pittsfield, Hancock is an outdoor enthusiast’s paradise, particularly for ski lovers. The town is known for its thrilling ski resorts and fields, offering exciting sports experiences for adventure seekers. With its breathtaking mountains and tranquil lakes, Hancock provides a stunning backdrop for winter sports. Whether you're hitting the slopes or enjoying the scenic peaks, this town is perfect for those looking to immerse themselves in nature and outdoor activities.

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 simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a significant difference, as prices tend to vary. Additionally, booking a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, continue with your existing arrangements, or review and manage your reservations. Your saved or booked properties are now neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, please visit: https://www.vrbo.com/en-ca/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)
Waubeeka Golf Links (14.4 mi / 23.2 km)
Balderdash Cellars (4.7 mi / 7.6 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:

Pleasant Valley Wilderness Sanctuary (4.4 mi / 7.2 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)
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 most popular type of vacation rental accommodation in Pittsfield?

Houses are the most popular kind of vacation rental in Pittsfield, according to our data. Even if you have something a little different in mind, Vrbo has properties in all shapes and sizes. Explore our options to find your perfect match.

How much does it cost to rent a vacation rental in Pittsfield?

Length of stay, season and property type are some things that can determine the price of a vacation home. Simply click on your dates of travel to find the ultimate escape. From comfy cabins to plush villas, all Vrbo vacation rentals provide unbeatable value.

How much does it cost to rent a beach house in Pittsfield?

When you travel and the style and size of the property will influence how much you’ll pay for your beachside vacation rental. Click on your Pittsfield travel dates to view your available options on Vrbo. Did someone just say “hot tub”? Use our filters to select the features and amenities you want in your rental.

Are there pet-friendly vacation rentals in Pittsfield?

Pack a travel bag for your pup because Pittsfield has 16 properties that roll out the welcome mat to pets. Let your four-legged pal have fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check the “Pets allowed” filter box.

Can I rent a house with a pool in Pittsfield?

Grab your swimwear and pool noodle, because there are seven houses with a private pool in Pittsfield. Base yourself at one of these terrific vacation homes and every day will be a pool day. Simply enter your travel dates into Vrbo, then use the “pool” filter to find the perfect place for a splashing good time!

What are popular rental amenities in Pittsfield?

Some of the most popular rental amenities people prefer in Pittsfield include a barbecue grill, a water view and a firepit. Whether you’re hitting the road with family, pals or even pets, Vrbo vacation properties have the best amenities for hanging out with the people you love.

Are there large group vacation rentals in Pittsfield?

Pittsfield has six vacation rentals that can accommodate 10 or more guests. These stays come with plenty of space to enjoy good times with friends and family.

Are there vacation rentals in Pittsfield that welcome kids?

Gather your whole crew for the adventure of a lifetime in Pittsfield at one of our 16 family-friendly vacation homes. Lots of these stays come with amenities that are ideal for trips with the kids, like kitchens, multiple bedrooms and outdoor spaces. Just check the “Properties good for families” filter and book your favorite.

What are the top attractions for families in Pittsfield?

Keep the kids happy at these popular family-friendly attractions in Pittsfield:

Berkshire Museum
Berkshire Scenic Railway Museum
Arrowhead Museum

Are there one-bedroom vacation rentals in Pittsfield?

Pittsfield has two one-bedroom rentals available. Typically situated in prime areas due to their smaller size, a one-bedroom vacation property is perfect if you’re traveling with a friend or your partner. And with plenty of home comforts like air conditioning and more privacy than a standard hotel, you’ll be able to kick back and relax while exploring this terrific destination.

Are there vacation rentals with WiFi in Pittsfield?

Pittsfield has six vacation rentals with WiFi, so you can stay connected during your vacation. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming TV shows with the family to sending emails, these Vrbo homes make it easy to go online.

How can I find vacation rentals with air conditioning in Pittsfield?

Pittsfield has 14 vacation rentals where you’ll be able to chill out in air-conditioned comfort. To locate a stay on Vrbo offering this perk, enter your preferred travel dates and use the filter tool to select the “air conditioning” box.

How old do you have to be to rent a vacation rental in Pittsfield?

You’ll need to check with the Pittsfield vacation home you want on Vrbo as age restrictions vary. However, generally it’s 16, 18 or 21.

How long can I rent a vacation rental in Pittsfield for?

It’s down to the Pittsfield property. To view all available options offering extended stays, simply enter your travel dates and guest number into Vrbo’s search page. Enjoy having the place to yourself, along with the comforts of home like a kitchen, air conditioning and an outdoor space where the little ones can play. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.