Book Holiday Homes in Pittsfield

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Pittsfield

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

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

Killington
With a stay at this vacation home in Killington, you'll be within a 15-minute drive of Killington Resort and Pico Mountain at Killington Ski Resort.
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont

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

Hartford
Located in White River Junction, this vacation home is a 1-minute drive from Quechee Ski Hill and 5 minutes from Maples.
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont
Cozy Private Bedroom with Own Entrance - No Shower

Cozy Private Bedroom with Own Entrance - No Shower

Middlebury
The price is AU$196 per night from 6 Apr to 7 Apr
AU$196
includes taxes & fees
6 Apr - 7 Apr
With a stay at this vacation home in Middlebury, you'll be in the mountains, just a 1-minute walk from Green Mountain National Forest and 8 minutes by foot from ...
Cozy Private Bedroom with Own Entrance - No Shower
Save an average of 15% on thousands of hotels when you're signed in
Spacious country home, beautiful sunsets, 40 acres

Spacious country home, beautiful sunsets, 40 acres

Tunbridge
This vacation home is 4.7 mi (7.5 km) from East Hill and 5.1 mi (8.1 km) from Tunbridge Public Library.
Spacious country home, beautiful sunsets, 40 acres
Classic Vermont Farmhouse near Sugarbush Resort

Classic Vermont Farmhouse near Sugarbush Resort

Warren
With a stay at this vacation home in Warren, you'll be in the mountains, within a 10-minute drive of Sugarbush Ski Resort and Green Mountain National ...
Classic Vermont Farmhouse near Sugarbush Resort
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

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

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, within a 15-minute drive of Killington Resort and Pico Mountain at Killington ...
☆ 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

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

Plymouth
Located in Plymouth, this vacation home is in the mountains, within a 15-minute drive of Long Trail Brewing Company and Coolidge State Park.
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

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

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, a 1-minute drive from Killington Resort and 9 minutes from Pico Mountain at Killington ...
The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

Killington
With a stay at this vacation home in Killington, you'll be within a 5-minute drive of Pico Mountain at Killington Ski Resort and Green Mountain National ...
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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
607 Holiday Homes
Lowest Price
AU$196
Highest Price
AU$216
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

Top trending hotels in Pittsfield

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

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

Pittsfield
With a stay at this vacation home in Pittsfield, you'll be in the mountains, just steps from Green Mountain National Forest and a 3-minute drive from Pittsfield ...
Killington area home - 4-seasons & hot tub. Sleeps 13+
Killington Vermont Ski and Snowmobiling House

Killington Vermont Ski and Snowmobiling House

Pittsfield
Located in Pittsfield, this vacation home is within a 15-minute drive of Pico Mountain at Killington Ski Resort and Killington Resort.
Killington Vermont Ski and Snowmobiling House
Private Killington Area Inn all to Yourself!

Private Killington Area Inn all to Yourself!

Pittsfield
With a stay at this vacation home in Pittsfield, you'll be on a river, within a 15-minute drive of Pico Mountain at Killington Ski Resort and Green Mountain ...
Private Killington Area Inn all to Yourself!
Save an average of 15% on thousands of hotels when you're signed in
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is AU$216 per night from 6 Apr to 7 Apr
AU$216
includes taxes & fees
6 Apr - 7 Apr
With a stay at Comfort Inn Rutland - Killington in Rutland, you'll be 0.6 mi (1 km) from Rutland Regional Medical Center and 9.8 mi (15.7 km) from Pico Mountain ...
Comfort Inn Rutland - Killington
Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.