Sit Back and Relax in Pittsfield Massachusetts Vacation Rentals

Consider visiting Pittsfield on your next trip to the Berkshires. Find out what you’ve been missing all these years you’ve reserved hotel rooms, and consider renting a Pittsfield vacation rental instead. Discover the extra space, privacy from other travelers and comfortable amenities that vacation homes provide. Whether you’re a single traveler in search of an affordable Pittsfield rental near the golf course, or a family of four who needs a spacious house rental, you’ll find a home on HomeAway that meets – and even exceeds – your needs.

Plenty to Do Near Pittsfield Rentals


Why travel to Pittsfield? There are several reasons why Pittsfield MA should be on your itinerary. Pittsfield has ended up on many “best of “lists, including “Most Secure Place to Live” and “Best Cities for Small Businesses” and “Green Cities.” In addition, Pittfield is home to a talented pool of creative people, whose artistry contributes to the city in the form of art galleries, theaters like the Colonial Theater and the Barrington Stage Company. It is truly the cultural hub of the Berkshires.

Visit Pittsfield MA During the Winter Months


Baseball is big in Pittsfield, home of the first intercollegiate baseball game. If you like the outdoors, spend time exploring the Pittsfield State Forest where you can hike or bike on hundreds of well kept trails among the beauty of the landscape. During the winter, head to Bousquet Ski Area where professional skiers and novices alike can find runs that fit their skill levels.

Choosing Your Pittsfield Berkshires Accommodations


Deciding on your Pittsfield vacation home can be difficult, but consider the search refinement options to your left to assist you in your search. Choose rental properties according to price range, dates available, number of bedrooms, and even amenities like hot tubs or swimming pools. Search for your Pittsfield rental today!

Looking for Berkshires rentals? Narrow down your search by destination: Becket apartments, Great Barrington condos, Lee condos, Lenox rentals, and Stockbridge houses!

Use filters to narrow your search results!

Pittsfield: Houses, Cottages & More(10)

10 Results
30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
#293547
  • 3 BR,
  • 1 BA,
  • Sleeps 8
#469617vb
(10)
2 night minimum stay
  • 7 BR,
  • 3 BA,
  • Sleeps 18
#251195vb
(8)
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
#310035vb
(14)
4 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 14
#420727vb
(8)
2 - 5 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 9
#564993vb
1 Review
2 - 7 night minimum stay
  • 6 BR,
  • 2 BA,
  • Sleeps 16
#296794vb
(14)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
#414727vb
(10)
$150 - $180
per night
2 - 3 night minimum stay
  • 3 BR,
  • Sleeps 8
#196944vb
(7)
  • 5 BR,
  • 3 BA,
  • Sleeps 10
#425380vb
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