Pittsfield holiday lettings

Why visit Pittsfield

• Outdoor Adventures: Enjoy a variety of activities such as skiing and hiking in the beautiful mountainous terrain surrounding Pittsfield.
• Historic Attractions: Explore charming historic sites and houses that reflect the rich heritage of the area.
• Family-Friendly Environment: Discover a welcoming atmosphere with numerous attractions suitable for all ages.
• Charming Downtown: Stroll through the inviting downtown area, complete with outdoor seating and local shops.
• Variety of Accommodations: Choose from private holiday homes, cosy cottages, and comfortable condos for your stay.

Popular types of accommodation in Pittsfield

If you’re seeking a getaway in Pittsfield, you’ll find a variety of delightful options to suit your needs. The most sought-after accommodations include houses, charming cottages, and comfortable condos. Whether you're looking for monthly rentals or a house rental for a weekend retreat, Pittsfield offers an array of choices to ensure a memorable stay. Discover the perfect Pittsfield house rental for your next adventure!

• Houses: The most sought-after option in Pittsfield, ideal for families or groups seeking a home-like atmosphere.
• Condos: A popular choice for those wanting modern amenities and a community feel during their stay.
• Cottages: Charming and cosy, these are perfect for a quaint getaway in the picturesque surroundings.
• Cabins: A delightful retreat for nature lovers, offering a rustic experience close to the great outdoors.
• Apartments: A practical option for solo travellers or couples, providing convenience and comfort in the heart of the city.**

Top attractions in and around Pittsfield

Pittsfield, Massachusetts, is perfect for a skiing and adventure holiday, offering a mix of historic sites, nature reserves, and mountainous terrain. Visitors can enjoy cultural experiences, outdoor activities, and family-friendly attractions. Whether you’re exploring historic houses or hiking in the beautiful surroundings, Pittsfield promises a delightful getaway for all types of travellers. Make sure to discover the local points of interest during your visit.

• Hancock Shaker Village: This historic village immerses you in the Shaker way of life, showcasing beautifully preserved buildings, gardens, and traditional crafts, providing a serene cultural experience.
• The Mount: The former home of author Edith Wharton, this historic house features stunning gardens and architecture, offering insights into her literary inspirations and the Gilded Age.
• National Shrine of the Divine Mercy: A peaceful shrine dedicated to divine mercy, it features beautiful chapels, serene grounds, and a welcoming atmosphere for reflection and prayer.

Things to do recommended for couples

For a romantic getaway in Pittsfield, indulge in a concert at Tanglewood Music Center, just 4.3km away. Enjoy skiing together at Jiminy Peak Mountain Resort, 5.0km away, or savour fine wines at Furnace Brook Winery, also 5.0km away, for a truly enchanting experience.

Things to do recommended for families

Families visiting Pittsfield can unwind at Kennedy Park, a serene recreational area just 3.1km away, or have fun at the Alpine Super Slide, located 4.3km from the city. Shatford Memorial Park, also 4.3km away, offers another relaxing spot for family enjoyment.

Things to do recommended for groups

Experience the vibrant arts at Barrington Stage Company for a delightful evening of theatre. Enjoy a round of golf at Skyline Country Club, just a short drive away, or explore the local flavours at Guido's Marketplace in the heart of Pittsfield. Perfect for group outings!

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

When travelling with a group, family, pets, or seeking longer stays, be sure to apply the appropriate filters to match your priorities. Here are some helpful booking tips for Vrbo.

• Traveling to Pittsfield with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Fortunately, you can easily refine your search for all of these options, and more, on Vrbo.
• Traveling to Pittsfield with young kids: Travelling with young children can present its own set of challenges. It's essential to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
• Taking your pets with you to Pittsfield: For many, a family holiday isn't truly fulfilled without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
• Planning for a long term stay visiting Pittsfield: If you're in search of holiday rentals offering 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 accommodations. It may also be worth considering additional amenities such as a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Pittsfield

Pittsfield, Massachusetts, offers a delightful blend of adventure and history, making it an ideal holiday destination. Explore the charming downtown, with its inviting outdoor seating and family-friendly atmosphere. Venture into the nearby regions for romantic getaways amidst stunning scenery. Whether you're seeking a budget-friendly escape or an action-packed ski trip, Pittsfield and its surroundings promise a memorable experience for every type of traveller.

• Lenox: Lenox is a charming town located approximately 4.3km from Pittsfield, renowned for its vibrant entertainment scene and romantic atmosphere. Visitors flock to Lenox for its world-class music concerts and theatrical performances, making it a perfect destination for culture enthusiasts. The surrounding natural beauty includes picturesque lakes and stunning mountains, ideal for outdoor activities. Additionally, Lenox is home to several event venues, allowing for a range of conferences and gatherings amidst scenic backdrops. Whether you're seeking a family-friendly outing or a romantic escape, Lenox offers a delightful experience.
• Stockbridge: Situated around 7.5km from Pittsfield, Stockbridge is a quintessential New England town steeped in culture and history. This enchanting locale is renowned for its artistic heritage and offers a variety of entertainment options, including music concerts and theatre productions. The town is also known for its beautiful lakes and notable landmarks such as monuments and shrines. With its charming streets, Stockbridge provides a romantic ambiance perfect for couples, while its cultural offerings ensure a memorable visit for all. Explore the town's rich artistic scene and enjoy the serene surroundings.
• Lee: Located about 6.2km from Pittsfield, Lee presents an inviting blend of romantic charm and family-friendly activities. This lovely town is well-regarded for its entertainment options, with a variety of theatres and music concerts to enjoy. Nature lovers will appreciate the nearby lakes and mountains, which provide ample opportunities for outdoor exploration. The town also boasts historical monuments, adding a touch of intrigue to your visit. Lee's welcoming atmosphere and diverse attractions make it an excellent choice for a delightful getaway.

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 keen to save on your next getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, you may find considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's pioneering Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or manage your travel arrangements with ease. You can conveniently locate properties you've previously saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.