Best apartment offers in Pittsfield, MA

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Pittsfield, MA apartments
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130 Best apartments in Pittsfield, MA

Best family friendly Pittsfield, MA Holiday Apartments and Self Catering Accommodations

Among the 130 accommodations in Pittsfield, MA, here are the 4 best family friendly holiday apartments

Berkshire’s Sweet Spot- Pool And Spa - Pittsfield, MA
9.9 83 reviews
Pittsfield, MA
13/10 – 18/10
₹34919/nighttotal: ₹174595 (5 )

Berkshire’s Sweet Spot- Pool And Spa

3 3
apartment , Pittsfield
This three-bedroom apartment is located in the heart of Berkshire County, just a short walk from Pittsfield's downtown area and within easy reach of both North and South County attractions. The apartment has been highly rated by previous guests for its cleanliness, location, and overall experience.
The apartment spans two floors and comfortably accommodates up to eight guests. Enjoy the private backyard with a seasonal pool, year-round spa, and a shared outdoor space with the other side of the duplex, ideal for larger groups.
Marie’s Place Unit 3 - Pittsfield, MA
9.9 58 reviews
Pittsfield, MA
06/09 – 13/09
₹30381/nighttotal: ₹212667 (7 )

Marie’s Place Unit 3

3 2
apartment , Pittsfield
This charming 3-bedroom house is located on a quiet street in southeast Pittsfield, just a short drive from local restaurants, shops, and popular attractions like Hancock Shaker Village and MASS MoCA. The home has received excellent ratings for location, cleanliness, and overall experience.
The house offers a spacious living area with a comfortable gas stove and new furniture, perfect for relaxing after a day of exploring. Guests can enjoy the home's amenities, including a fully equipped kitchen, air conditioning, a large garden, and ample off-street parking.
Charming Beautiful Apartment In Central Pittsfield - Pittsfield, MA
9.2 78 reviews
Pittsfield, MA
06/09 – 13/09
₹14300/nighttotal: ₹100100 (7 )

Charming Beautiful Apartment In Central Pittsfield

1 2
apartment , Pittsfield
This two-bedroom apartment in Pittsfield is located just 2 kilometres from the town centre and 3 kilometres from the lake, offering easy access to both the vibrant town and the tranquil lakeside. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The property offers a spacious living space suitable for up to 5 guests. Guests can enjoy a range of amenities including a fully equipped kitchen, air conditioning, a private garden, off-street parking, and a washer and dryer.
Cozy Bungalow In Se Pittsfield - Pittsfield, MA
9.9 28 reviews
Pittsfield, MA
06/09 – 13/09
₹22183/nighttotal: ₹155281 (7 )

Cozy Bungalow In Se Pittsfield

1 2
apartment , Pittsfield
This apartment is located in the Berkshires, a short drive from Pittsfield, just 5 km from Bousquet Ski Mountain and 20 km from Jiminy Peak, making it a great choice for those looking to explore the region's natural beauty and outdoor activities. It has received excellent ratings for location, cleanliness, and overall experience.
This single-storey property can accommodate up to 5 guests and offers a comfortable and private stay. It includes a fully equipped kitchen, a garden, a deck and an enclosed porch, as well as access to a grill and yard games, perfect for relaxing and enjoying the outdoors.

Best Pittsfield, MA holiday apartments with a kitchen

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-ski On/off Country Inn Redone - Pittsfield, MA
10 12 reviews
Pittsfield, MA
03/07 – 06/07
₹36786/nighttotal: ₹110358 (3 )

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-ski On/off Country Inn Redone

1 2
apartment , Hancock
This Hancock slopeside apartment building is situated in the mountains, within 3km of Jiminy Peak Mountain Resort, offering ski-in/ski-out access and proximity to Pittsfield State Forest and Mount Greylock State Reservation (within 10km).
This 46 square metre apartment features two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen, indoor pool, fitness centre, hot tub, garden, and parking; enjoy nearby attractions such as the Alpine Super Slide and Mountain Coaster (within 3km).
Beautiful Waterfront Home With Deep Water Dock On Onota Lake. Huge Covered Deck. - Pittsfield, MA
9.6 85 reviews
Pittsfield, MA
13/10 – 25/10
₹44505/nighttotal: ₹534060 (12 )

Beautiful Waterfront Home With Deep Water Dock On Onota Lake. Huge Covered Deck.

3 2
apartment , Pittsfield
This waterfront holiday home in Pittsfield offers direct access to Onota Lake, located a short distance from the Tanglewood Music Centre and the Crane Museum of Papermaking, with the Colonial Theatre and Herman Melville's Arrowhead also nearby.
This spacious 167 square meter residence accommodates up to 10 guests across 3 bedrooms and 2 bathrooms, featuring a large dock, expansive outdoor living space with a covered deck and sunroom, and modern climate control, ideal for water sports, cultural excursions, and nearby outdoor pursuits.
Brady’s Croft | Berkshires Farmhouse Retreat - Pittsfield, MA
Pittsfield, MA
21/08 – 24/08
₹67107/nighttotal: ₹201321 (3 )

Brady’s Croft | Berkshires Farmhouse Retreat

1 6
apartment , Pittsfield
Brady's Croft is a restored Berkshire farmhouse located near state forest trails, 10 kilometres from Tanglewood, 3 kilometres from Jiminy Peak, and just 1 kilometre from Onota Lake and 1.1 kilometres from Pontoosuc Lake.
This family-friendly property offers accommodation for up to 10 guests in 5 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, a playroom, a wraparound porch, and a garden gazebo with a fire table, providing ample space for gatherings and easy access to outdoor recreation.
Lovely Ranch Home Getaway In The Berkshires- Just 6 Miles To Tanglewood - Pittsfield, MA
9.6 18 reviews
Pittsfield, MA
13/10 – 25/10
₹28823/nighttotal: ₹345876 (12 )

Lovely Ranch Home Getaway In The Berkshires- Just 6 Miles To Tanglewood

2 2
apartment , Richmond
This charming farmhouse is located just 10 kilometres from popular Berkshire attractions like Tanglewood, Kripalu, Shakespeare & Company, and the Norman Rockwell Museum, offering a peaceful escape in a rural setting. The property has received excellent reviews from previous guests, highlighting its comfort and amenities.
This home has two bedrooms and two bathrooms, comfortably accommodating up to four guests. Guests can enjoy a private deck with views, a large yard, a fire pit, a tree swing, a gas grill for outdoor dining, and a fully equipped kitchen.

Frequently asked questions about apartment rentals in Pittsfield, MA

  • What are the must-see attractions for a 2 days stay in Pittsfield, MA?

    For a two-day trip, you should definitely visit the Berkshire Museum, which has a fantastic collection of art and natural history exhibits. The Clark Art Institute is another must-see, featuring Impressionist and early modern paintings. If you're interested in theatre, the Barrington Stage Company puts on great shows throughout the year.
  • Which neighborhoods in Pittsfield, MA are best for renting an apartment?

    The best neighbourhoods for renting an apartment in Pittsfield are probably the ones near downtown, like the Morningside or the West Side. You'll be close to shops, restaurants, and the Berkshire Museum. The historic district is also a popular choice, with its beautiful Victorian architecture.
  • What are the top cultural and historical sites in Pittsfield, MA?

    Pittsfield has a rich history and culture. The Berkshire Museum is a great place to start, with exhibits on local history, art, and science. The Williams College Museum of Art is also worth a visit, featuring a diverse collection of art from around the world. Don't forget to check out the historic houses in the city's historic district.
  • What makes Pittsfield, MA unique or famous?

    Pittsfield is known for its beautiful scenery, surrounded by the Berkshire Mountains. It's also a popular destination for arts and culture, with the renowned Tanglewood Music Center just a short drive away. The city is also home to the Berkshire Museum, which is known for its diverse collection of exhibits.
  • Where can you find the best local markets and street food in Pittsfield, MA?

    The best local markets in Pittsfield are the Pittsfield Farmers Market, which takes place on Saturdays in the summer, and the Downtown Pittsfield Farmers Market, held on Thursdays in the summer. You'll find a great selection of local produce, baked goods, and crafts. For street food, there are a few food trucks that rotate through the city, especially during summer events.
  • How is the public transportation system in Pittsfield, MA?

    Pittsfield has a public bus system, the Berkshire Regional Transit Authority (BRTA), which operates routes throughout the city and surrounding towns. It's a good option for getting around, especially if you're staying in the downtown area. However, it's not as extensive as in larger cities, so you might need to rely on taxis or ride-sharing services for some trips.
  • Which seasonal events or festivals should apartment renters look forward to in Pittsfield, MA?

    Pittsfield has a lot of exciting events throughout the year. In the summer, you can enjoy the Pittsfield Farmers Market, the Tanglewood Music Festival, and the Pittsfield Theatre Festival. In the fall, the city hosts the Berkshire Autumn Festival, with craft vendors, food, and live music. And in the winter, there's the Pittsfield Holiday Stroll, with festive decorations and holiday events.
  • What amenities are typically included in apartments in Pittsfield, MA?

    Most apartments in Pittsfield will include basic amenities like a stove, refrigerator, and oven. Some apartments might also include a dishwasher, washer, and dryer, depending on the building and the specific unit. It's always best to check with the landlord or property manager to confirm what amenities are included.

Destinations nearby

Best Pittsfield, MA holiday apartments with air conditioning

Beautiful Renovated Home, Close To Multiple Ski Mountains. - Pittsfield, MA
Pittsfield, MA
30/06 – 31/10
₹30152/nighttotal: ₹3708696 (123 )

Beautiful Renovated Home, Close To Multiple Ski Mountains.

3 1
apartment , Hinsdale
This Hinsdale holiday home is conveniently located within 14.5 kilometres of Bas Ridge Golf Course, the Kushi Institute, and Canoe Meadows Wildlife Sanctuary.
The three-bedroom, three-bathroom property sleeps up to ten guests and includes in-house laundry facilities, ensuring a comfortable stay with easy access to local amenities and attractions.
Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4 - Pittsfield, MA
9.4 10 reviews
Pittsfield, MA
30/06 – 31/10
₹15199/nighttotal: ₹1869477 (123 )

Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4

1 1
apartment , Hancock
This family-friendly apartment, situated at the base of Jiminy Peak Mountain in Hancock, Massachusetts, offers direct access to the Country Inn and its amenities, including a heated pool and fitness centre.
The 50 sq m self-catering suite sleeps four, featuring a King bed, a queen sofa bed, a well-equipped kitchenette with appliances including an air fryer and dishwasher, and unique gamer-themed décor including a PS4 and arcade game.
Renovated Pittsfield Colonial By Evergreen Home - Pittsfield, MA
9.9 100 reviews
Pittsfield, MA
13/10 – 18/10
₹72887/nighttotal: ₹364435 (5 )

Renovated Pittsfield Colonial By Evergreen Home

4 3
apartment , Pittsfield
This charming colonial home is situated in a central location in the Berkshires, just 16 kilometres from Tanglewood and 48 kilometres from Jiminy Peak, offering easy access to Pittsfield's attractions. The property has consistently received excellent ratings for its cleanliness, location, and user experience.
The apartment spans 362 square metres and comfortably accommodates up to 12 guests across its four bedrooms. A modern kitchen, a private garden, and a fitness centre are just some of the amenities that guarantee a comfortable and enjoyable stay.
Downtown Apartment A - Pittsfield, MA
9.9 100 reviews
Pittsfield, MA
13/10 – 25/10
₹18127/nighttotal: ₹217524 (12 )

Downtown Apartment A

1 2
apartment , Pittsfield
This two-bedroom flat is located in a quiet neighbourhood in Pittsfield, just 5km from Bousquet Ski Area and a short drive from Jimmy Peak, Tanglewood, Mass MoCA, and a variety of restaurants. This property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The flat offers ample space for relaxation and privacy, comfortably accommodating up to four guests. Guests can enjoy a fully equipped kitchen, air conditioning, parking, and internet access, as well as the convenience of being close to hiking and biking trails, making it an ideal base for exploring the Berkshires.

Best pet-friendly Pittsfield, MA holiday apartments

Among the 130 accommodations in Pittsfield, MA, here are the 4 best pet friendly holiday apartments

Quiet Studio In Desirable Neighborhood - Pittsfield, MA
10 6 reviews
Pittsfield, MA
06/09 – 13/09
₹18698/nighttotal: ₹130886 (7 )

Quiet Studio In Desirable Neighborhood

1 2
apartment , Pittsfield
This Pittsfield studio apartment is centrally located in the city's Historic District, a short 4.8-kilometre drive from Berkshire Medical Center and 5.6 kilometres from General Dynamics Mission Systems.
The self-contained apartment, sleeping up to two guests, offers a kitchen with dishwasher, air conditioning, a shared laundry, and access to a swimming pool and garden; plus it's within walking distance of restaurants, theatres, shops and museums.
Berkshire Lakehouse - 3 Bedrooms - Sleeps 5 - Pittsfield, MA
9.8 45 reviews
Pittsfield, MA
13/10 – 18/10
₹29113/nighttotal: ₹145565 (5 )

Berkshire Lakehouse - 3 Bedrooms - Sleeps 5

3 3
apartment , Pittsfield
This three-bedroom Pittsfield lakeside house, boasting excellent guest reviews, offers direct access to Onota Lake with a private dock and is conveniently located near Pittsfield's ski slopes and hiking trails, the precise distance unspecified.
Sleeping up to five guests, this self-catering property features a fully equipped kitchen, a large deck with mountain views, a fenced yard, on-site laundry, and access to kayaks and paddleboards; a BBQ area is also available in the shared backyard.
House W/ View In The Berkshires. - Pittsfield, MA
9.8 8 reviews
Pittsfield, MA
21/08 – 24/08
₹54379/nighttotal: ₹163137 (3 )

House W/ View In The Berkshires.

1 6
apartment , Pittsfield
This charming house is situated in the Berkshires, just 30km from attractions like Tanglewood, The Mount, and MassMoca, offering a peaceful retreat in a picturesque setting. The house is ideal for families and groups of friends, with three bedrooms and two bathrooms, accommodating up to seven guests.
The house features a modern open-plan layout with a fully equipped kitchen, a garden, and a wrap-around deck with stunning views of the surrounding lake and mountains. Guests can enjoy al fresco dining, relax in the spacious living area, or explore the nearby hiking trails and state forests.
Berkshire Getaway Ranch 3 Acres + Saltwater Pool - Pittsfield, MA
9.8 101 reviews
Pittsfield, MA
13/10 – 18/10
₹36179/nighttotal: ₹180895 (5 )

Berkshire Getaway Ranch 3 Acres + Saltwater Pool

2 3
apartment , Pittsfield
This two-bedroom apartment is situated in the Berkshires, just a short drive (under 8km) from Pittsfield, with easy access to Onota and Pontoosuc lakes, as well as popular ski resorts. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment offers a spacious layout, accommodating up to 7 guests, with multiple living areas, including a sun room and a secondary living room with a wet bar. Guests can enjoy a range of amenities, including a private saltwater pool, a well-equipped kitchen, a fitness centre, and a two-car garage.
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