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Pittsfield, MA apartments
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202 Holiday apartments Pittsfield, MA

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

Among the 202 accommodations in Pittsfield, MA, here are the 4 best family friendly holiday apartments

Lovely Ranch Home Getaway In The Berkshires- Just 6 Miles To Tanglewood - Pittsfield, MA
9.6 20 reviews

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

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.
Centrally Located In The Berkshires - Cozy Bungalow In Se Pittsfield! - Pittsfield, MA
10 5 reviews

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

apartment, Pittsfield
This charming bungalow is situated in the city centre of Pittsfield, just 5km from Bousquet Ski Resort, 20km from Jiminy Peak and 15km from Tanglewood in Lenox, offering easy access to the area's attractions. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The home sleeps up to 5 guests and spans 93 square metres. It features a fully equipped kitchen, a spa, air conditioning and a private deck with a grill, perfect for enjoying the outdoors.
3 Bedroom Home W/ Lake And Mountain Views Near Skiing, And Cultural Attractions! - Pittsfield, MA
8.4 9 reviews

3 Bedroom Home W/ Lake And Mountain Views Near Skiing, And Cultural Attractions!

apartment, Pittsfield
This pet-friendly apartment is located in Pittsfield, just 8km from Pittsfield State Forest and 5km from the Crane Museum of Papermaking, offering easy access to outdoor activities and local attractions. The apartment is suitable for families and groups, accommodating up to 6 guests in 3 bedrooms and 2 bathrooms.
The apartment comes fully equipped with a kitchen, a washer and dryer, a private patio, a fireplace and a barbecue, providing everything you need for a comfortable and enjoyable stay. You can also enjoy Wi-Fi, a Smart TV, air conditioning, and a work desk.
Comfy Quaint Tavern - Pittsfield, MA
10 72 reviews

Comfy Quaint Tavern

apartment, Pittsfield
This one-bedroom flat is situated in the southeast section of Pittsfield, a residential area with a couple of restaurants and a seasonal ice cream shop within walking distance. The property has excellent user, location, and cleanliness ratings.
The flat is suitable for up to three guests and includes a living room with a queen-sized pull-out sofa. It is equipped with modern amenities such as a dishwasher, air conditioning, and off-street parking, as well as a 12-foot bar with stools for relaxation and a small park across the street for outdoor recreation.

Best Pittsfield, MA holiday apartments with a kitchen

Lenox Grand Colonial With Pool By Evergreen Home - Pittsfield, MA
10 45 reviews

Lenox Grand Colonial With Pool By Evergreen Home

apartment, Lenox
This spacious Lenox house, situated on a quiet cul-de-sac, is 1.6km from downtown Lenox and Tanglewood, and 0.3km from shops and restaurants, offering easy access to Berkshire attractions including Bousquet Ski Area (5 minutes away).
The 279 sq m property boasts four bedrooms sleeping eight, a fully equipped kitchen, a private pool, a large primary bedroom with jacuzzi, plus amenities such as a Weber grill, ping pong, and access to major streaming services; ideal for families or groups.
Relaxing Berkshire Getaway - Pittsfield, MA
9.9 73 reviews

Relaxing Berkshire Getaway

apartment, Pittsfield
This charming two-bedroom house is located in a residential area of Pittsfield, just a short walk from Pontoosuc Lake and a short drive from the city centre. It has received excellent ratings for location, cleanliness and user experience.
The house can accommodate up to six guests and features a spacious living room with a pull-out bed, a well-equipped kitchen, and a sunroom with stunning lake views. Guests can enjoy a range of amenities, including a gas grill, bikes, and corn hole boards, as well as access to nearby hiking trails, biking paths, and shopping.
Renovated Pittsfield Colonial By Evergreen Home - Pittsfield, MA
9.9 101 reviews

Renovated Pittsfield Colonial By Evergreen Home

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.
Cozy & Safe, New One Bedroom Apartment - Pittsfield, MA
9.9 20 reviews

Cozy & Safe, New One Bedroom Apartment

apartment, Pittsfield
This three-bedroom apartment in Pittsfield, Massachusetts, is situated in a peaceful neighbourhood a few minutes' drive from the city centre and within easy reach of cultural attractions such as Tanglewood and Mass MoCA.
The self-catering property sleeps seven guests and features a spacious living area, a fully equipped kitchen with a fridge, private enclosed backyard with porch and grill, plus free on-site parking and internet access.

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.

Popular destinations

Best Pittsfield, MA holiday apartments with air conditioning

Cozy Escape To The Berkshires - Pittsfield, MA
10 3 reviews

Cozy Escape To The Berkshires

apartment, Pittsfield
This two-bedroom flat in Southeast Pittsfield provides a quiet base, conveniently located for accessing Berkshire attractions such as the Clark Art Institute and Tanglewood, as well as skiing and hiking opportunities within a 30 kilometre radius.
The accommodation offers a fully equipped kitchen, a king-sized bed and a queen-sized bed, a large bathroom with a walk-in shower, a separate half-bathroom with a washer and dryer, and Smart TVs throughout, comfortably accommodating up to four guests with keyless entry.
Downtown Apartment A - Pittsfield, MA
9.9 107 reviews

Downtown Apartment A

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.
Lake Views & Dock Access - Pittsfield Cottage! - Pittsfield, MA
10 9 reviews

Lake Views & Dock Access - Pittsfield Cottage!

apartment, Lanesborough
This four-bedroom lakefront property, located in Pittsfield, a short drive from Lanesborough, offers direct access to Pontoosuc Lake and is ideally situated for exploring the area.
The self-catering holiday home sleeps six guests, boasts a private boat dock with kayaks and canoes, a furnished sunroom, ample parking, and modern amenities including Wi-Fi, a gas fireplace, and air conditioning.
Sunny 1 Bedroom Apartment Spacious Downtown - Pittsfield, MA
8.5 11 reviews

Sunny 1 Bedroom Apartment Spacious Downtown

apartment, Pittsfield
This Pittsfield apartment, a first-floor unit in a two-unit home, offers easy access to various Berkshire attractions; precise distances to specific landmarks require further information.
The self-catering property boasts a spacious layout with separate living and dining areas, accommodating up to three guests and including a full-sized washer/dryer, a fenced garden with a hammock, and off-street parking for two cars.

Best pet-friendly Pittsfield, MA holiday apartments

Among the 202 accommodations in Pittsfield, MA, here are the 4 best pet friendly holiday apartments

Lenox Grand Colonial With Pool By Evergreen Home - Pittsfield, MA
10 3 reviews

Lenox Grand Colonial With Pool By Evergreen Home

apartment, Lenox
This Lenox holiday home is situated in a rural setting, less than 3km from the Housatonic River and the historical Arrowhead, home of Herman Melville.
This four-bedroom, three-bathroom property boasts 281 square metres of living space, a private pool, barbecue facilities, and sleeps eight guests, offering free Wi-Fi and a fully equipped kitchen.
Dharma Grove - Bask In The Light - Pittsfield, MA
10 1 review

Dharma Grove - Bask In The Light

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.
Extended Stay- Full Kitchen 1br Apartment In Downtown Pittsfield - Pittsfield, MA
10 1 review

Extended Stay- Full Kitchen 1br Apartment In Downtown Pittsfield

apartment, Pittsfield
This one-bedroom flat in Pittsfield is conveniently located for exploring local culture and history, with Tanglewood Music Center and Colonial Theater just a short distance away, and Herman Melville's Arrowhead and Hancock Shaker Village also nearby.
This apartment offers accommodation for up to four guests, featuring a king-size bed, a sofa bed in the living room, air conditioning, and complimentary Wi-Fi, and is within easy reach of the Berkshire Museum and Bousquet Ski Area.
Spacious Historic Home In The Berkshires! - Pittsfield, MA
9.7 21 reviews

Spacious Historic Home In The Berkshires!

apartment, Pittsfield
This five-bedroom holiday home is situated just a short distance from Pittsfield town centre, offering easy access to restaurants, shops and cultural attractions, and is only 11 kilometres from Tanglewood. The pet-friendly property features a fully equipped kitchen, a fireplace, a soaker tub, a covered porch, a barbecue and a garden, making it ideal for families or groups of up to nine people.
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