Best apartment offers in Pittsfield, MA

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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

Beautiful Waterfront Home With Deep Water Dock On Onota Lake. Huge Covered Deck. - Pittsfield, MA
9.6 89 reviews

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

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.
Visit Us 3 Minutes From Tanglewood Music Hall And Kripalu Yoga Center - Pittsfield, MA
No reviews

Visit Us 3 Minutes From Tanglewood Music Hall And Kripalu Yoga Center

apartment, Lenox
This Lenox flat is conveniently located 240 metres from the Housatonic River and 400 metres from Guido's Marketplace.
This 93 square metre apartment offers one bedroom, one bathroom, air conditioning, Wi-Fi, and on-site parking, with Jiminy Peak Mountain Resort and Kennedy Park nearby.
Maries Place Unit 3 - Pittsfield, MA
9.9 76 reviews

Maries Place Unit 3

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.
3 Bed Home Lake & Mountain Views - Pittsfield, MA
9.3 12 reviews

3 Bed Home Lake & Mountain Views

apartment, Pittsfield
This three-bedroom house is situated near a lake just off Route 7, providing easy access to both North and South Berkshire County attractions, including the vibrant city of Pittsfield, located approximately 10km away. The property offers a comfortable space for families or groups, with a fully equipped kitchen, two bathrooms, a furnished basement, and a new deck with a BBQ grill.

Best Pittsfield, MA holiday apartments with a kitchen

Comfortable Charming Home In The Town Of Dalton - Pittsfield, MA
No reviews

Comfortable Charming Home In The Town Of Dalton

apartment, Dalton
This two-bedroom flat in Dalton is situated in a peaceful neighbourhood, offering easy access to local amenities and parks.
This recently renovated apartment, accommodating up to four guests, features accessible design, air conditioning, parking for three vehicles, a kitchen with a fridge, and a laundry room, with a semi-private garden for relaxation.
Beautiful Blue Studio Downtown 5 Mins To Downtown - Pittsfield, MA
9.3 73 reviews

Beautiful Blue Studio Downtown 5 Mins To Downtown

apartment, Pittsfield
This Pittsfield studio apartment is conveniently located a 0.8-kilometre walk from downtown, offering easy access to numerous cafes, shops, and restaurants.
The self-contained apartment sleeps two guests and includes a kitchen, air conditioning, parking, and excellent Wi-Fi; nearby attractions include the Barrington Stage Company and the Pittsfield Historical Society.
Spacious Green 2 Bedroom Downtown - Pittsfield, MA
9.6 51 reviews

Spacious Green 2 Bedroom Downtown

apartment, Pittsfield
This centrally located Pittsfield flat is a 0.8 km walk from local cafes, restaurants, and a cinema.
The two-bedroom apartment, sleeping up to five guests, offers in-unit laundry, designated off-street parking, and a well-equipped kitchen including a fridge, microwave, and dishwasher.
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.

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.

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Best Pittsfield, MA holiday apartments with air conditioning

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.

Best pet-friendly Pittsfield, MA holiday apartments

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

Architectural Lenox Escape W/pool And Sauna - Pittsfield, MA
10 8 reviews

Architectural Lenox Escape W/pool And Sauna

apartment, Lenox
This Lenox designer retreat, a three-bedroom, two-bathroom apartment, is situated in a secluded wooded setting with immediate access to hiking trails, just 3.2 kilometres from Lenox town centre and 3.2 kilometres from a ski resort.
The 232-square-metre property boasts a fully equipped kitchen, spacious sunroom, large-screen movie system, high-speed internet, a saltwater pool, Finnish sauna, and parking, comfortably accommodating six guests and offering easy access to local attractions, festivals, and museums.
Scroll No More - Your Magical Lenox Place - Pittsfield, MA
10 7 reviews

Scroll No More - Your Magical Lenox Place

apartment, Lenox
This charming house is situated just a short distance from Lenox town centre, offering easy access to its shops, restaurants and cultural attractions. The property has received excellent ratings for its cleanliness, location and overall guest experience.
The spacious three-bedroom house can comfortably accommodate up to four guests. It features a fully equipped kitchen, a relaxing garden, a Jacuzzi and parking, as well as internet access.
New Built - Split Level House In The Berkshires - Pittsfield, MA
10 4 reviews

New Built - Split Level House In The Berkshires

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.
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.
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