Book Holiday Homes in Pittsfield
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Featured Holiday Homes in Pittsfield
Spacious country home, beautiful sunsets, 40 acres
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
Spectacular 4 Bed Killington Home
Slopeside Chalet - Ski to and from your home!
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
Luxurious guest home with private art gallery in the heart of a historic village
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
The Brandon Inn - King Room
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 | 462 Holiday Homes |
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Lowest Price | AU$186 |
Highest Price | AU$1,096 |
Popular accommodation | Spacious country home, beautiful sunsets, 40 acres, Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen, Spectacular 4 Bed Killington Home, Slopeside Chalet - Ski to and from your home!, Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated, Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail, Luxurious guest home with private art gallery in the heart of a historic village, Dog-friendly cabin with forest setting, woodstove & deck - near Killington, The Brandon Inn - King Room |
Top Locations for Holiday Homes in Pittsfield
More accommodations in Pittsfield
Top trending hotels in Pittsfield
Killington area home - 4-seasons & hot tub. Sleeps 12+
Killington Mountain Lodge, Tapestry Collection by Hilton
Comfort Inn Trolley Square
Days Inn by Wyndham Rutland/Killington Area
More ways to explore Pittsfield
Top picks
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^Subject to availability and chosen travel dates.