Pittsfield Holiday Homes
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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

Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn
Holiday Accommodation Pittsfield
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Pittsfield are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Pittsfield itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Pittsfield holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Pittsfield, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Pittsfield with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
Pittsfield Holiday Homes essential information
Accommodation | 626 Holiday Homes |
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Lowest Price | NZ$169 |
Highest Price | NZ$826 |
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, Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn, Off Grid Glamping Shed with River Access , Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola |
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Killington area home - 4-seasons & hot tub. Sleeps 13+
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