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Featured Holiday Homes in Pittsfield

Spacious country home, beautiful sunsets, 40 acres

Spacious country home, beautiful sunsets, 40 acres

Tunbridge
This vacation home is 11.5 mi (18.6 km) from Gifford Medical Center and 20.9 mi (33.6 km) from Silver Lake State Park.
Spacious country home, beautiful sunsets, 40 acres
Quiet Modern Luxury Home w/  Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Bridgewater
With a stay at this vacation home in Bridgewater Corners, you'll be on a river, within a 15-minute drive of Killington Resort and Long Trail Brewing ...
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
Spectacular 4 Bed Killington Home

Spectacular 4 Bed Killington Home

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, a 2-minute drive from Killington Resort and 8 minutes from Pico Mountain at Killington ...
Spectacular 4 Bed Killington Home
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Slopeside Chalet - Ski to and from your home!

Slopeside Chalet - Ski to and from your home!

Killington
The price is AU$1,096 per night from 3 Nov to 4 Nov
AU$1,096
includes taxes & fees
3 Nov - 4 Nov
When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and a 4-minute drive from Bear Mountain Quad ...
Slopeside Chalet - Ski to and from your home!
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and 15 minutes by foot from Sunrise Village ...
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

Killington
With a stay at this vacation home in Killington (North Sherburne), you'll be within a 15-minute drive of Killington Resort and Pico Mountain at Killington Ski ...
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

Luxurious guest home with private art gallery in the heart of a historic village

Brandon
With a stay at this vacation home in Brandon, you'll be within a 10-minute walk of Judith Reilly Gallery and Stephen A Douglas Birthplace.
Luxurious guest home with private art gallery in the heart of a historic village
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Plymouth
With a stay at this vacation home in Plymouth, you'll be within a 10-minute drive of Skyeship Express Gondola Stage I and Calvin Coolidge Homestead.
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
The Brandon Inn - King Room

The Brandon Inn - King Room

Brandon
A stay at this vacation home places you in the heart of Brandon, within a 10-minute walk of Judith Reilly Gallery and Stephen A Douglas Birthplace.
The Brandon Inn - King Room
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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
462 Holiday Homes
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 trending hotels in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 12+

Killington area home - 4-seasons & hot tub. Sleeps 12+

Pittsfield
Located in Pittsfield, this vacation home is in the mountains, within a 15-minute drive of Green Mountain National Forest and White River Golf Club.
Killington area home - 4-seasons & hot tub. Sleeps 12+
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd, Killington, VT
Fully refundableReserve now, pay when you stay
The price is AU$243 per night from 19 Nov to 20 Nov
AU$243
includes taxes & fees
19 Nov - 20 Nov
With a stay at Killington Mountain Lodge, Tapestry Collection by Hilton in Killington, you'll be next to a golf course, just steps from Killington Resort and ...
Killington Mountain Lodge, Tapestry Collection by Hilton
Comfort Inn Trolley Square

Comfort Inn Trolley Square

2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 14 Nov to 15 Nov
AU$186
includes taxes & fees
14 Nov - 15 Nov
With a stay at Comfort Inn Trolley Square 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 at ...
Comfort Inn Trolley Square
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Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is AU$187 per night from 12 Nov to 13 Nov
AU$187
includes taxes & fees
12 Nov - 13 Nov
When you stay at Days Inn by Wyndham Rutland/Killington Area in Rutland, you'll be near ski lifts, within a 5-minute drive of Vermont State Fairgrounds and Rutland ...
Days Inn by Wyndham Rutland/Killington Area
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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.

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^Subject to availability and chosen travel dates.