Book Holiday Homes in Pittsfield
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Featured Holiday Homes in Pittsfield

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont

Cozy Private Bedroom with Own Entrance - No Shower

Spacious country home, beautiful sunsets, 40 acres

Classic Vermont Farmhouse near Sugarbush Resort

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
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 | 626 Holiday Homes |
---|---|
Lowest Price | NZ$218 |
Highest Price | NZ$666 |
Popular accommodation | Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi, Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont, Cozy Private Bedroom with Own Entrance - No Shower, Spacious country home, beautiful sunsets, 40 acres, Classic Vermont Farmhouse near Sugarbush Resort, ☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace, Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi, The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA, Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski |
More accommodations in Pittsfield
Top trending hotels in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 13+

Comfort Inn Rutland - Killington

Woodstock Inn & Resort

Killington Mountain Lodge, Tapestry Collection by Hilton
More ways to explore Pittsfield
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^Subject to availability and chosen travel dates.