Book Holiday Homes in Pittsfield
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Featured Holiday Homes in Pittsfield
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Amore Estate - beautiful room with many places to explore and relax in.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Secluded Family Home in Serene Stockbridge Woods
Spectacular views and close to Great Barrington.
Berkshire Village Carriage House - Super Private!!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Pittsfield Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Pittsfield vacation homes are the perfect way for you to wing it.
Holiday houses in Pittsfield let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Pittsfield in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Pittsfield adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Pittsfield with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Pittsfield vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Pittsfield Holiday Homes essential information
Accommodation | 335 Holiday Homes |
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Lowest Price | AU$134 |
Highest Price | AU$820 |
Popular accommodation | Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con, Amore Estate - beautiful room with many places to explore and relax in., Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!, Secluded Family Home in Serene Stockbridge Woods, Spectacular views and close to Great Barrington., Berkshire Village Carriage House - Super Private!!, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Cozy Home In The Berkshires, Pet Friendly with fenced in yard!, 4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi |
Holiday Homes in Pittsfield
Top Locations for Holiday Homes in Pittsfield
More accommodations in Pittsfield
Top trending hotels in Pittsfield
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
FairBridge Inn Express
Berkshire Mountain Lodge
Hotel On North
More ways to explore Pittsfield
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.