Pittsfield holiday lettings

We found 1,034 holiday rentals — enter your dates for availability

Discover a selection of 39 homes and other holiday rentals in Pittsfield that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for hanging out with the people that matter most, including parking and a TV. No matter what you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Pittsfield

Showing deals for:10 Jul - 17 Jul

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10 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)

Best of the Berkshires & Hudson Valley

Canaan

8% off
Price is £3,057
for 7 nights, 1 home
£437 per night
includes taxes & fees
Best of the Berkshires & Hudson Valley

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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.

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 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.

**Based on Vrbo properties bookings.

Explore the lakeside setting in Pittsfield

Take a holiday to Pittsfield and enjoy the area's entertainment, theatre scene and opera. This city's baseball games, museums and cycling draw many visitors. With a holiday 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

Are you hoping to discover attractions to see in the area? Venture out of your holiday home and experience everything that makes Pittsfield a one-of-a-kind holiday spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Waubeeka Golf Links (14.4 mi / 23.2 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 an active traveller or just want to take in the scenery, Pittsfield is a great place to get outside. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport options to and around Pittsfield

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 2.5 mi (4 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away.

If you're travelling 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 holiday rental?
When considering a holiday rental in Pittsfield, Massachusetts, the downtown area is an excellent choice. This vibrant neighbourhood offers a charming mix of historical architecture and modern amenities, making it a delightful base for exploring the region. You'll find a variety of properties available, from cosy apartments to more spacious homes, suiting different group sizes and preferences.

Staying downtown puts you within walking distance of several attractions, such as the Berkshire Museum, which features a fascinating collection of art, history, and natural sciences. Additionally, the nearby Colonial Theatre regularly hosts a range of performances, adding to the cultural richness of the area. For those who enjoy outdoor activities, the nearby Pittsfield State Forest offers numerous hiking trails and beautiful natural scenery.

Another appealing neighbourhood is the Morningside area, known for its lovely residential streets and proximity to public parks. Here, you can find properties that provide a more suburban feel while still being close to the city's amenities. The Morningside area is also near Burbank Park, which features scenic walking paths and recreational facilities.
How much does it cost to rent a holiday home in Pittsfield?
Prices for holiday 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 holiday 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 those seeking ski resort rentals near Pittsfield, Massachusetts, the nearby Jiminy Peak Mountain Resort is a top choice. Located just a short drive away in Hancock, this ski area offers a variety of accommodation options, including condos and chalets that cater to families and groups. Many of these properties come equipped with essential amenities, such as full kitchens, spacious living areas, and often access to communal facilities like hot tubs and heated pools, great for relaxing after a day on the slopes.

In Pittsfield itself, visitors can find charming rental homes and apartments that provide a cozy base for exploring the region. Some of these properties feature amenities like fireplaces, outdoor decks, and proximity to local dining and shopping, enhancing the overall experience. The city is also known for its cultural attractions, with nearby galleries and theatres, making it an ideal spot for those who enjoy both winter sports and arts.

For outdoor enthusiasts, the surrounding Berkshire Mountains offer additional hiking and recreational opportunities during the off-season, ensuring that there's plenty to explore beyond skiing.
What is the most popular type of holiday rental accomodation in Pittsfield?
In Pittsfield, holiday houses are the most popular type of holiday rental, with around 136 available throughout the area. These houses typically offer spacious living environments suitable for families or groups, featuring multiple bedrooms, fully equipped kitchens, and often outdoor spaces for relaxation. Many are located in residential neighbourhoods, providing a tranquil setting close to local attractions like the Berkshire Museum and the scenic Pittsfield State Forest. Additionally, there are about 20 apartments, which provide a more compact and convenient option for couples or solo travellers, often including amenities like kitchenettes and living areas. Condos and cottages, with around 12 each, also add variety to the rental landscape, suiting different preferences.
Are there any family house rentals in Pittsfield?
In Pittsfield, Massachusetts, there are numerous family-friendly house rentals available, with around 32 options scattered throughout the city. The neighbourhoods offer a variety of accommodations, many of which feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces superb for children to play. Amenities such as Wi-Fi and laundry facilities are commonly included, ensuring a comfortable stay for families.

Visitors will find that Pittsfield is conveniently located near attractions like the Berkshire Museum, which offers engaging exhibits for all ages, and the nearby Bousquet Mountain, where families can enjoy outdoor activities year-round. The surrounding scenic beauty of the Berkshires also provides ample opportunities for hiking and exploring nature, making it an ideal destination for those seeking both relaxation and adventure.
Can I rent a holiday home with a pool or hot tub in Pittsfield?
In Pittsfield, Massachusetts, several holiday homes are available for rent that feature pools and hot tubs, making it a delightful option for those seeking relaxation during their stay. The area offers a variety of neighbourhoods, each with its unique charm. Properties can be found in residential areas that provide a peaceful atmosphere, ideal for families or groups looking to unwind.

Travellers can expect various amenities in these rentals, including private pools and hot tubs, spacious outdoor patios, and fully equipped kitchens for self-catering. Some homes may also include features such as game rooms or large gardens, enhancing the overall experience.
Can I find long-stay holiday rentals in Pittsfield?
A long-stay holiday rental in Pittsfield is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Pittsfield?
In Pittsfield, there are numerous pet-friendly house rentals available, offering a variety of options for those travelling with furry companions. Many of these rentals are equipped with comfortable living spaces, fully stocked kitchens, and outdoor areas where pets can roam. The properties often feature amenities such as fenced yards, making them ideal for both relaxation and play.

The city is in close proximity to several parks that welcome pets, including Burbank Park, which offers walking trails and scenic views of the water, great for leisurely strolls with your dog. Additionally, the nearby Pittsfield State Forest provides ample opportunities for hiking and exploring nature, with its extensive trails and beautiful landscapes.
Are there any remote work holiday rentals in Pittsfield?
In Pittsfield, Massachusetts, there are numerous remote work holiday rentals available, with around 176 options to choose from. This charming city offers a variety of accommodations that cater to those needing to balance work and leisure. Many of these properties come equipped with dedicated office spaces, high-speed internet, and amenities such as Wi-Fi in rooms and access to printers, making them ideal for remote workers.

Located in the beautiful Berkshire region, these rentals often feature comfortable living areas and fully equipped kitchens, allowing for a pleasant and productive stay. The area is rich in cultural attractions, including museums and theatres, and offers outdoor activities such as hiking and skiing in the nearby mountains. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pittsfield holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Pittsfield with parking available—perfect for families or travellers 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 rental amenities include kitchens, fireplaces, and onsite parking, making it convenient for guests to settle in comfortably. Many properties also feature coffee and tea makers for a warm beverage after a day of exploring the area. Additionally, outdoor spaces such as decks or patios are common, providing a pleasant spot for relaxation and enjoying the fresh air.
When is the best time to visit Pittsfield for a holiday rental?
The peak travel season in Pittsfield runs from June to August, with July being the most popular month. This vibrant period attracts visitors looking to immerse themselves in outdoor activities, cultural events, and the stunning natural beauty of the Berkshires. With warm temperatures averaging between 20 and 30 degrees Celsius, it's the superb time to explore the area's hiking trails, visit art galleries, or attend local festivals.

During the summer months, you can enjoy a range of activities, from boating on nearby lakes to attending concerts in the park. The lively option makes it an ideal choice for families and groups seeking memorable experiences together.

For those considering a more budget-friendly option, visiting in December can be a great choice. Although it falls outside the main tourist season, the charm of Pittsfield during the winter months offers unique attractions, such as holiday festivities and a quieter pace for exploring the town's historical sites. It's a delightful time to enjoy the beauty of the Berkshires dusted in snow.
How early should I book a Pittsfield holiday rental?
Book your Pittsfield holiday 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 holiday 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 variety of attractions that showcase the area's natural beauty and cultural heritage. The Berkshire Museum, located in the downtown area, features a diverse collection of art, science, and historical exhibits, making it a great stop for families and art enthusiasts alike. Nearby, the historic Colonial Theatre hosts various performances, including concerts and plays, contributing to the local cultural scene.

For outdoor enthusiasts, the nearby Pittsfield State Forest offers an array of hiking and biking trails, as well as opportunities for fishing and wildlife observation, making it a superb destination for those looking to immerse themselves in nature. Additionally, the stunning views from the summit of Mount Greylock, the highest peak in Massachusetts, are just a short drive away, providing ample opportunities for hiking and photography.

In the summer, the city's parks, such as Burbank Park on Pontoosuc Lake, offer recreational activities including swimming, boating, and picnicking.
Can I change or cancel my Pittsfield home rental booking on Vrbo?
To find Pittsfield holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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