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Pittsfield, MA apartments
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130 Apartments or condos in Pittsfield, MA

Search Family-Friendly Vacation Apartments in Pittsfield, MA

Discover kid-friendly vacation apartments in Pittsfield, MA that put city attractions within easy reach for a stress-free trip.

Centrally Located In The Berkshires - Cozy Bungalow In Se Pittsfield! - Pittsfield, MA
10 5 reviews
Pittsfield, MA
09/06 – 09/13
$197/nighttotal: $1379 (7 )

Centrally Located In The Berkshires - Cozy Bungalow In Se Pittsfield!

2 2
apartment , Pittsfield
This centrally located bungalow in Pittsfield is just minutes away from popular attractions such as Bousquet Ski Resort, hiking trails, museums, and Tanglewood in Lenox. It offers easy access to urban amenities, and has been rated as "excellent" by previous guests.
The bungalow has a floor area of 1000 square feet and can accommodate up to 5 guests. It has 2 bedrooms, 1 bathroom, a kitchen with a fridge, microwave oven, and dishwasher, and air conditioning. The bungalow also features a spa, an outdoor deck, a yard with games and a grill, and convenient access to hiking trails and museums.
Disney Magic Suite At Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat - Pittsfield, MA
9.8 21 reviews
Pittsfield, MA
07/03 – 07/06
$386/nighttotal: $1158 (3 )

Disney Magic Suite At Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

1 2
apartment , Hancock
This apartment is located just a short distance from Jiminy Peak Mountain Resort and within easy reach of other attractions like Zema's Nursery and Pittsfield State Forest. It has received excellent user ratings, making it a popular choice for travelers.
The one-bedroom apartment spans 500 square feet and comfortably accommodates up to 4 guests. It offers a range of amenities, including a fully equipped kitchen, a fireplace, a swimming pool, a jacuzzi, and convenient parking.
Beautiful Waterfront Home With Deep Water Dock On Onota Lake. Huge Covered Deck. - Pittsfield, MA
9.6 85 reviews
Pittsfield, MA
10/13 – 10/18
$520/nighttotal: $2600 (5 )

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

3 3
apartment , Pittsfield
This waterfront vacation home on Onota Lake in Pittsfield offers direct access to water sports and is located within 3 miles of Tanglewood Music Center, Crane Museum of Papermaking, and Colonial Theater, with Bousquet Ski Area just 2 miles away.
This 1800 square foot house features 3 bedrooms, 2 bathrooms, sleeps 10, and includes a modern kitchen with a fridge, microwave, and dishwasher, plus a private dock and a large covered deck for outdoor enjoyment.
3 Bedroom , 2 Bath, Beautifully Appointed Home - Pittsfield, MA
9.8 43 reviews
Pittsfield, MA
10/13 – 10/18
$392/nighttotal: $1960 (5 )

3 Bedroom , 2 Bath, Beautifully Appointed Home

3 3
apartment , Pittsfield
This Pittsfield home is conveniently located near popular attractions like Tanglewood, the Norman Rockwell Museum, and Mass MOCA, making it a great base for exploring the city. The home has received excellent ratings for its location, cleanliness, and overall experience.
This 3-bedroom, 2-bathroom house comfortably accommodates up to 6 guests. Amenities include a fully equipped kitchen, air conditioning, a garden, and a fitness center, ensuring a comfortable and enjoyable stay.

Best Pittsfield, MA apartment rentals with a kitchen

Berkshire’s Sweet Spot- Pool And Spa - Pittsfield, MA
9.9 83 reviews
Pittsfield, MA
09/06 – 09/13
$427/nighttotal: $2989 (7 )

Berkshire’s Sweet Spot- Pool And Spa

3 2
apartment , Pittsfield
This Pittsfield duplex is conveniently located in central Berkshire County, within walking distance of downtown and close to attractions like Mass MoCa, Tanglewood, and the natural falls. The apartment boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The three-bedroom, one-bathroom rental comfortably accommodates up to eight guests. Enjoy a private backyard with a seasonal in-ground pool and a year-round spa, along with modern amenities like updated kitchens, bathrooms, smart televisions, and a relaxing porch.
Lake House Onota Lake - Pittsfield, MA
10 2 reviews
Pittsfield, MA
09/06 – 09/13
$276/nighttotal: $1932 (7 )

Lake House Onota Lake

1 2
apartment , Pittsfield
This three-bedroom, two-bathroom lakeside house on Lake Onota in Pittsfield, Massachusetts, is minutes from several ski areas and a 15-minute drive from Tanglewood.
The 8-guest home offers direct lake access for swimming and boating, a fully equipped kitchen, parking, internet, and proximity to numerous outdoor recreational opportunities.
Renovated Jiminy Peak Mountainside Condo\ndesigner Interiors  Walk To Slopes - Pittsfield, MA
Pittsfield, MA
07/03 – 07/06
$977/nighttotal: $2931 (3 )

Renovated Jiminy Peak Mountainside Condo\ndesigner Interiors Walk To Slopes

3 2
apartment , Hancock
This tri-level condo is located in Jiminy Peak's Mountainside area, a short walk to the mountain, lifts, and village amenities.
This professionally refreshed 3-bedroom, 4-bathroom condo accommodates up to 8 guests and features a fully updated kitchen with new appliances, two king primary suites, a kid-friendly bunk room, and is equipped with internet and parking.
Downtown Apartment A - Pittsfield, MA
9.9 100 reviews
Pittsfield, MA
10/13 – 10/18
$186/nighttotal: $930 (5 )

Downtown Apartment A

1 3
apartment , Pittsfield
This Pittsfield apartment is conveniently located in a quiet neighborhood, just 5 minutes from Bousquet Ski Area and close to Jimmy Peak, making it ideal for winter sports enthusiasts. The apartment has received excellent ratings for user experience, location, and cleanliness.
The apartment is a 2-bedroom rental that can accommodate up to 4 guests. It features a full kitchen with a fridge, freezer, and microwave oven, along with air conditioning, parking, and internet access. The apartment is close to Tanglewood, Mass MoCA, hiking trails, and a variety of restaurants, offering easy access to cultural and outdoor activities.

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 stay, you should definitely check out the Berkshire Museum. It's a great place to learn about the region's history and culture. You should also visit the Clark Art Institute, which has a beautiful collection of Impressionist and Post-Impressionist art. If you're looking for something a little different, head over to the Barrington Stage Company, a renowned regional theater that puts on fantastic productions.
  • What are the best apartments in Pittsfield, MA?

    Among the apartments in Pittsfield, MA, Large Guest Suite W/private Bath In The Berkshires, Honeysuckle Rose Cottage and Marie's Place are the most popular ones.

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

    The best neighborhoods for renting an apartment in Pittsfield are probably the ones around downtown. You'll be close to all the action, including restaurants, shops, and bars. If you're looking for something a little quieter, the neighborhoods around the Berkshire Museum and the Clark Art Institute are nice and peaceful.
  • What are the best apartments with a pool in Pittsfield, MA?

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

    Pittsfield is rich in culture and history. The Berkshire Museum is a must-see, showcasing local history, science, and art. The Clark Art Institute is another gem, housing an impressive collection of Impressionist and Post-Impressionist paintings. For a taste of the city's vibrant performing arts scene, catch a show at the Barrington Stage Company.
  • What are the best apartments with a jacuzzi in Pittsfield, MA?

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

    You can find some great local markets and street food in Pittsfield. The Pittsfield Farmers Market is held every Saturday from June to October. It's a great place to pick up fresh produce, baked goods, and other local products. For a quick bite, check out the food trucks that gather in the city center during the summer months. They offer a variety of cuisines, from Mexican to Thai.
  • What are the best apartments for families and kids in Pittsfield, MA?

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

    Pittsfield's public transportation system is decent, but it's not as extensive as in larger cities. The Berkshire Regional Transit Authority (BRTA) operates bus routes throughout the city and surrounding towns. If you plan on exploring the area, it's best to have a car.
  • What are the best pet friendly apartments in Pittsfield, MA?

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

    Pittsfield has many seasonal events and festivals throughout the year. The annual Tanglewood Music Festival is a highlight in the summer, featuring world-renowned classical musicians. In the fall, you can enjoy the vibrant colors of the foliage during the Berkshires Fall Foliage Festival. And, of course, there's always the holiday season, which is celebrated with festive events and decorations throughout the city.
  • What are the best apartments with parking in Pittsfield, MA?

    Large Guest Suite W/private Bath In The Berkshires, Honeysuckle Rose Cottage and Marie's Place are the best apartments with parking in Pittsfield, MA.

  • What amenities are typically included in apartments in Pittsfield, MA?

    Most apartments in Pittsfield include basic amenities like central heating and air conditioning, a refrigerator, stove, and oven. You'll also find that many apartments have in-unit laundry or access to a shared laundry facility. Some apartments may have additional amenities like a dishwasher, a balcony, or a parking space.

Destinations nearby

Best Pittsfield, MA apartment rentals with air conditioning

Cantabile Life In The Berkshires - Pittsfield, MA
9.9 210 reviews
Pittsfield, MA
10/13 – 10/18
$340/nighttotal: $1700 (5 )

Cantabile Life In The Berkshires

1 3
apartment , Pittsfield
This apartment is located in a quiet, friendly neighborhood in Pittsfield, just minutes from several lakes, mountains, and attractions like Tanglewood and Bousquet Ski Area. It boasts excellent ratings for location, cleanliness, and user satisfaction.
The rental offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the spacious living areas, well-equipped kitchen, and outdoor space, plus family-friendly amenities like games, a piano, and child-friendly equipment.
Wow-new Ski Onoff Suite By Pool Sleeps 4 Jiminy Pk - Pittsfield, MA
8.0 21 reviews
Pittsfield, MA
07/01 – 07/31
$184/nighttotal: $5520 (30 )

Wow-new Ski Onoff Suite By Pool Sleeps 4 Jiminy Pk

1 1
apartment , Hancock
This Hancock, MA apartment offers convenient access to Jiminy Peak, approximately 20 miles from both Tanglewood and Cranwell Spa & Golf Club.
This 500-square-foot unit features one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, and access to a swimming pool, jacuzzi, and fitness center.
Marie's Place, Unit 1 - Pittsfield, MA
9.9 114 reviews
Pittsfield, MA
10/13 – 10/18
$277/nighttotal: $1385 (5 )

Marie's Place, Unit 1

3 3
apartment , Pittsfield
This Pittsfield apartment is conveniently located just a 7-minute drive from the Bosquet ski area and 28 minutes from Jiminy Peak, making it ideal for winter sports enthusiasts. The apartment enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This 3-bedroom rental can accommodate up to 6 guests and features a spacious eat-in kitchen and living room. Enjoy the enclosed front porch or the small outside deck, relax with the provided wet towel basket, and take advantage of the off-street parking for two cars.
Spacious Historic Home In The Berkshires! - Pittsfield, MA
9.8 14 reviews
Pittsfield, MA
10/13 – 10/18
$519/nighttotal: $2595 (5 )

Spacious Historic Home In The Berkshires!

5 3
apartment , Pittsfield
This Pittsfield vacation home offers convenient access to the Colonial Theatre, Berkshire Athenaeum, and Berkshire Museum, all within a 10-minute walk, and is less than a mile from the Housatonic River and Barrington Stage Company.
This 3,300-square-foot house features seven bedrooms, two bathrooms, accommodates nine guests, and includes a fully equipped kitchen, fireplace, in-house washer, private garden, balcony, and parking.

Neighborhoods and points of interest in Pittsfield, MA

Popular Pet-Friendly Apartments in Pittsfield, MA

No need to leave your dog behind; each vacation apartment in Pittsfield, MA on this list offers nearby dog parks and city walks.

Dharma Grove - Bask In The Light - Pittsfield, MA
Pittsfield, MA
09/06 – 09/13
$468/nighttotal: $3276 (7 )

Dharma Grove - Bask In The Light

3 2
apartment , Richmond
This 3-bedroom, 2-bathroom Richmond rental is located on 2.5 acres, offering a quiet retreat just 1 minute from Balderdash Cellars and 4 minutes from Hancock Shaker Village.
This 2060 sq ft home accommodates up to 6 guests and features a fully-equipped kitchen, high-speed Wi-Fi, free parking, a garden, terrace, and is dog-friendly.
Lenox Grand Colonial With Pool By Evergreen Home - Pittsfield, MA
10 3 reviews
Pittsfield, MA
10/13 – 10/18
$751/nighttotal: $3755 (5 )

Lenox Grand Colonial With Pool By Evergreen Home

4 3
apartment , Lenox
This Lenox vacation home is situated in a rural setting, two miles from the Housatonic River, Arrowhead Museum, and Herman Melville's Arrowhead.
This 3,020-square-foot house features four bedrooms, three bathrooms, sleeps eight guests, and includes a private pool, fully equipped kitchen, and free Wi-Fi.
Cozy Escape To The Berkshires - Pittsfield, MA
10 3 reviews
Pittsfield, MA
10/13 – 10/18
$194/nighttotal: $970 (5 )

Cozy Escape To The Berkshires

1 3
apartment , Pittsfield
This Southeast Pittsfield rental is situated in a quiet neighborhood perfect for walks, offering convenient access to the Berkshires' museums, music venues, theaters, skiing, and hiking.
This two-bedroom, one-bathroom suite accommodates up to four guests and features a fully stocked kitchen, a king-sized bed, a queen-sized bed, a walk-in shower, an in-unit washer and dryer, keyless entry, and Smart TVs.
Family Fun In The Berkshires At Beautiful Hygge House - Pittsfield, MA
9.9 81 reviews
Pittsfield, MA
09/06 – 09/13
$581/nighttotal: $4067 (7 )

Family Fun In The Berkshires At Beautiful Hygge House

1 2
apartment , Richmond
Hygge House is a spacious apartment located in the Berkshires, a scenic region of western Massachusetts, near Richmond Pond, just 7 miles from Tanglewood and 9 miles from Pleasant Valley Wildlife Sanctuary. This apartment has excellent user, location, and cleanliness ratings.
The apartment offers 2100 square feet of space, with 3 bedrooms, 2 bathrooms, and can accommodate up to 6 guests. Hygge House boasts a well-equipped kitchen, a cozy living room with a fireplace, multiple living areas, a sunroom, a kids' corner, a yoga/meditation space, and a spacious master bedroom with a reading nook.
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