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Pittsfield, MA apartments
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130 Holiday apartments 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

Family Fun In The Berkshires At Beautiful Hygge House - Pittsfield, MA
9.9 81 reviews
Pittsfield, MA
06/09 – 13/09
SG$747/nighttotal: SG$5229 (7 )

Family Fun In The Berkshires At Beautiful Hygge House

1 2
apartment , Richmond
Hygge House is situated in the Berkshires, a central region of Massachusetts, 24 kilometres from Mount Greylock State Reservation and 14.5 kilometres from Mass Audubon's Pleasant Valley Wildlife Sanctuary. This property has received excellent ratings for its location, cleanliness, and overall user experience.
This three-bedroom, two-bathroom home spans 195 square metres and comfortably accommodates up to six guests. The house offers a range of amenities, including private water access, two nearby beaches, fishing opportunities, hiking trails, a fireplace, multiple living areas, a well-equipped kitchen, a children's play area, a yoga/meditation space, and the option to arrange in-home massage services and meals prepared by local chefs.
Attractive Condo In The Berkshires. - Pittsfield, MA
9.7 40 reviews
Pittsfield, MA
06/09 – 13/09
SG$253/nighttotal: SG$1771 (7 )

Attractive Condo In The Berkshires.

1 2
apartment , Pittsfield
This apartment is located in a great neighbourhood in Pittsfield, just a short distance from the river and a canoe launch. It has consistently received excellent ratings for cleanliness, location and user experience.
This charming three-bedroom property can accommodate up to six guests and offers a fully equipped kitchen, washer and dryer, a garage and storage space. Enjoy the convenience of a garden, air conditioning and internet access, as well as the unique charm of colonial lighting and tasteful design.
Cozy Cottage In Berkshires: Minutes To Jiminy Peak - Pittsfield, MA
9.9 77 reviews
Pittsfield, MA
21/08 – 24/08
SG$489/nighttotal: SG$1467 (3 )

Cozy Cottage In Berkshires: Minutes To Jiminy Peak

4 6
apartment , Lanesborough
Polly's Place, a four-bedroom Lanesborough holiday home, is situated near the summit of a hill, approximately 1.6km from the Ashuwillticook Rail Trail, 1.3km from Elle Day Spa, and 5.6km from the Mount Greylock Visitor Centre.
This self-catering property sleeps six guests and boasts a 1960s Tappan range, a sunken sunroom with fireplace, modern amenities including smart TVs and Bose speakers, plus a large garden perfect for outdoor games; it's even been a favourite retreat for Olympic skier Mikaela Shiffrin.
Beautiful Waterfront Home With Deep Water Dock On Onota Lake. Huge Covered Deck. - Pittsfield, MA
9.6 85 reviews
Pittsfield, MA
13/10 – 18/10
SG$655/nighttotal: SG$3275 (5 )

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

3 3
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.

Best Pittsfield, MA holiday apartments with a kitchen

The Reel Retreat | Theatre & Firepit  Game Room - Pittsfield, MA
10 5 reviews
Pittsfield, MA
06/09 – 13/09
SG$473/nighttotal: SG$3311 (7 )

The Reel Retreat | Theatre & Firepit Game Room

4 2
apartment , Pittsfield
This southern Pittsfield holiday home, minutes from both Pittsfield and Lenox town centres, provides easy access to Berkshire attractions such as Tanglewood (approximately 16km away).
The four-bedroom, two-bathroom property sleeps seven, boasting a fully equipped kitchen, private garden with deck and BBQ, a dedicated cinema room, and a games room with foosball and Pac-Man; nearby activities include the Barrington Stage Company and Bousquet Ski Area.
Charming Lakeview Cottage In The Berkshires - Pittsfield, MA
10 9 reviews
Pittsfield, MA
13/10 – 25/10
SG$263/nighttotal: SG$3156 (12 )

Charming Lakeview Cottage In The Berkshires

1 2
apartment , Pittsfield
This lakefront property on Onota Lake in the Berkshires offers stunning 180-degree views and is a short distance from Pittsfield's cultural attractions.
The one-bedroom, one-bathroom cottage sleeps four, features a fully equipped kitchen, air conditioning, a private beach, and direct lake access, making it ideal for families seeking a relaxing getaway near Pittsfield.
Hearts Desire Is Your Private Escape. - Pittsfield, MA
10 107 reviews
Pittsfield, MA
18/10 – 21/10
SG$400/nighttotal: SG$1200 (3 )

Hearts Desire Is Your Private Escape.

2 3
apartment , Lanesborough
This three-bedroom house is situated on a lake in Lanesborough, Massachusetts, just 9.6 kilometres from Mount Greylock State Reservation, offering stunning lake views and proximity to the highest peak in Massachusetts.
The property features a Jacuzzi, a terrace, a garden, and parking, and can accommodate up to six guests, making it ideal for families or groups of friends looking for a relaxing getaway.
Ski In & Ski Out Deluxe Condo - Pittsfield, MA
8.0 1 review
Pittsfield, MA
30/06 – 31/10
SG$864/nighttotal: SG$106272 (123 )

Ski In & Ski Out Deluxe Condo

1 1
apartment , Hancock
This Hancock apartment offers ski-in/ski-out access directly from Jiminy Peak Ski Resort.
The one-bedroom condo sleeps five, features a fully equipped kitchen, two flat-screen TVs, a king-size bed and queen-size sofa bed, plus access to a swimming pool, jacuzzi, fitness centre, and parking.

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 exhibits on art, science and natural history. Also, don't miss the Clark Art Institute, which has a collection of Impressionist and Post-Impressionist paintings. And if you're interested in theatre, the Barrington Stage Company puts on a great season of plays.
  • What are the best apartments in Pittsfield, MA?

  • Which neighborhoods in Pittsfield, MA are best for renting an apartment?

    The best neighbourhoods for renting an apartment are the ones near the downtown area. They're within walking distance of shops, restaurants and the Berkshire Museum. The area around the Berkshire Mall is also good, as it has a lot of amenities. If you're looking for something quieter, the area around the Clark Art Institute is a good option.
  • What are the best apartments with a pool in Pittsfield, MA?

  • What are the top cultural and historical sites in Pittsfield, MA?

    Pittsfield is known for its cultural and historical sites. The Berkshire Museum is a great place to learn about the area's history and art. The Clark Art Institute is another must-see, and its collection of Impressionist and Post-Impressionist paintings is world-renowned. The Colonial Theatre is a beautiful historic theatre that hosts a variety of performances.
  • What are the best apartments with a jacuzzi in Pittsfield, MA?

  • What makes Pittsfield, MA unique or famous?

    Pittsfield is known for its beautiful scenery and its vibrant arts and culture scene. It's also home to the Clark Art Institute, which has a world-renowned collection of Impressionist and Post-Impressionist paintings. And the city has a rich history, with many historic buildings and landmarks.
  • What are the best apartments for families and kids in Pittsfield, MA?

  • Where can you find the best local markets and street food in Pittsfield, MA?

    Pittsfield has a great farmers' market on Saturdays in the summer, where you can find fresh produce, baked goods and local crafts. The city also has a few food trucks that park in different locations throughout the week. And if you're looking for a quick bite, there are plenty of cafes and restaurants in the downtown area.
  • What are the best pet friendly apartments in Pittsfield, MA?

  • How is the public transportation system in Pittsfield, MA?

    Pittsfield has a public transportation system that includes buses. The system is not as extensive as in larger cities, but it can get you around the city and to nearby towns. The Berkshire Regional Transit Authority operates the buses.
  • What are the best apartments with parking in Pittsfield, MA?

  • Which seasonal events or festivals should apartment renters look forward to in Pittsfield, MA?

    Pittsfield has a lot of great seasonal events, including the Pittsfield Farmers Market, the Berkshire Arts & Crafts Fair, and the First Night Pittsfield celebration. The city also hosts a number of music festivals throughout the year.
  • What amenities are typically included in apartments in Pittsfield, MA?

    Apartments in Pittsfield typically include basic amenities like central heating and air conditioning, a refrigerator, stove and oven. Some apartments may also have a dishwasher, washer and dryer, and a balcony or patio. You can find apartments with a range of features, from basic to luxurious, depending on your budget.

Destinations nearby

Best Pittsfield, MA holiday apartments with air conditioning

New Built - Split Level House In The Berkshires - Pittsfield, MA
Pittsfield, MA
21/08 – 24/08
SG$929/nighttotal: SG$2787 (3 )

New Built - Split Level House In The Berkshires

1 6
apartment , Lanesborough
This newly built Lanesborough residence is situated on a quiet street, a mere 300 metres from Pontoosuc Lake, and a short drive to Jiminy Peak for skiing, the Ashuwillticook Rail Trail for cycling, and Pittsfield State Park for its natural beauty.
This spacious three-bedroom, three-bathroom house accommodates up to eight guests and includes amenities such as air conditioning, Wi-Fi, a kitchen, and parking for four vehicles, with outdoor EV charging available.
Newly Renovated, And Spacious Great For Family - Pittsfield, MA
9.4 92 reviews
Pittsfield, MA
06/09 – 13/09
SG$130/nighttotal: SG$910 (7 )

Newly Renovated, And Spacious Great For Family

1 2
apartment , Pittsfield
This one-bedroom apartment is situated in the centre of Pittsfield, within walking distance of the city's main attractions and restaurants.
The newly renovated apartment features a fully equipped kitchen, a jacuzzi, and a private parking space in the backyard, making it perfect for a couple seeking a comfortable and stylish stay.
Spacious 4 Br+ House In The Heart Of Berkshires - Pittsfield, MA
9.9 72 reviews
Pittsfield, MA
06/09 – 13/09
SG$449/nighttotal: SG$3143 (7 )

Spacious 4 Br+ House In The Heart Of Berkshires

5 2
apartment , Pittsfield
This five-bedroom, two-bathroom house in Pittsfield offers excellent wheelchair access via a wide wooden ramp and is conveniently located near hiking and skiing trails, and within easy driving distance of Tanglewood.
Sleeping up to nine guests, the property boasts a well-equipped kitchen, a spacious garden, parking for four cars, and individual climate control in each of its rooms, including two with work areas and a separate office.
The Reel Retreat | Theatre & Firepit • Game Room - Pittsfield, MA
10 16 reviews
Pittsfield, MA
06/09 – 13/09
SG$425/nighttotal: SG$2975 (7 )

The Reel Retreat | Theatre & Firepit • Game Room

4 2
apartment , Pittsfield
This three-bedroom Pittsfield apartment, ideal for families or groups of up to seven, is situated a short distance from both Pittsfield and Lenox town centres, offering easy access to the Berkshires' attractions.
The property boasts a fully equipped kitchen, a private cinema room, games room, spacious backyard with deck and barbecue, and parking; all within a comfortable dwelling.

Best pet-friendly Pittsfield, MA holiday apartments

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

Pine & Paddle | Pond Access • Kayaks - Pittsfield, MA
9.9 15 reviews
Pittsfield, MA
06/09 – 13/09
SG$488/nighttotal: SG$3416 (7 )

Pine & Paddle | Pond Access • Kayaks

2 2
apartment , Richmond
This two-bedroom flat in Richmond offers a country cottage ambiance with a private community beach on Richmond Pond, situated a short walk from Tanglewood and Bousquet ski area.
This pet-friendly accommodation for four features a wood-burning fireplace, a back balcony with woodland views, and a newly renovated kitchen, with access to a tandem kayak for use on Richmond Pond.
Dharma Grove - Bask In The Light - Pittsfield, MA
10 1 review
Pittsfield, MA
06/09 – 13/09
SG$602/nighttotal: SG$4214 (7 )

Dharma Grove - Bask In The Light

3 2
apartment , Richmond
This Richmond flat offers a secluded Berkshire escape on 2.5 acres, located a short drive from Balderdash Cellars (1.6 kilometres), Hancock Shaker Village (6.4 kilometres), Bousquet Mountain Ski Area (14.5 kilometres), Tanglewood (22.5 kilometres), and the Norman Rockwell Museum (27.4 kilometres).
This 191 square metre residence accommodates up to six guests with three bedrooms and two bathrooms, featuring a fully equipped kitchen, an outdoor grill, high-speed Wi-Fi, and a garden, with pets welcome for a one-time fee.
Modern Gem In The Heart Of Berkshires - Pittsfield, MA
9.9 67 reviews
Pittsfield, MA
06/09 – 13/09
SG$296/nighttotal: SG$2072 (7 )

Modern Gem In The Heart Of Berkshires

1 2
apartment , Pittsfield
This two-bedroom apartment is conveniently located in Pittsfield, just 10 kilometres from Bousquet Ski Resort and 15 kilometres from Jiminy Peak. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment is suitable for up to four guests and features a spacious living and dining area, a well-equipped kitchen, a screened-in porch, and a shared backyard. Guests can enjoy amenities such as air conditioning, internet access, a washing machine and dryer, and a modern bathroom with a double vanity.
3 Br+ 4level Winter Ski Rental\n Looking 4 Seasonal Renter\n 1 Mile Off Of Jiminey - Pittsfield, MA
9.5 32 reviews
Pittsfield, MA
30/06 – 31/10
SG$376/nighttotal: SG$46248 (123 )

3 Br+ 4level Winter Ski Rental\n Looking 4 Seasonal Renter\n 1 Mile Off Of Jiminey

4 1
apartment , Lanesborough
This Lanesborough apartment is situated in a mountain setting, less than 5 kilometres from Jiminy Peak Mountain Resort and Mount Greylock State Reservation.
This 163-square-metre property offers four bedrooms, two bathrooms, sleeps ten guests, and boasts a private jacuzzi, terrace, swimming pool, fitness centre, and tennis court, alongside free Wi-Fi.
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