Book Holiday Homes in Pittsfield
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Featured Holiday Homes in Pittsfield
Killington, Vermont Ski House w/ Hot Tub and Sauna
Walk to Pickle Barrel & Jax. Hot tub & Views
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Ski-in/out sunrise condo with pool & hot tub - great ski retreat
Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests
Killington Getaway In Private Community
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 | 468 Holiday Homes |
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Lowest Price | NZ$296 |
Highest Price | NZ$2,126 |
Popular accommodation | Killington, Vermont Ski House w/ Hot Tub and Sauna, Walk to Pickle Barrel & Jax. Hot tub & Views, Dog-friendly cabin with forest setting, woodstove & deck - near Killington, Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail, Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!, BruinsDen - Ski On Ski Off (Home Stretch Trail), Ski-in/out sunrise condo with pool & hot tub - great ski retreat, Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests, Killington Getaway In Private Community |
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 Rutland - Killington
North Star Lodge and Resort
More ways to explore Pittsfield
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^Subject to availability and chosen travel dates.