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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sep - 13 Sep

Our top choices for Pittsfield vacation homes

Outdoor dining

Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont

Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont
South Royalton
The price is AED 476
AED 558 total
includes taxes & fees
7 Jun - 8 Jun
Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont
Private kitchen

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is AED 364
AED 889 total
includes taxes & fees
24 May - 25 May
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
TV, DVD player, offices

Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm

Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm
Woodstock
The price is AED 962
AED 2,345 total
includes taxes & fees
27 May - 28 May
Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm
Interior

CozyDen - AC, Grill, Bike to Mountain, Porch!

CozyDen - AC, Grill, Bike to Mountain, Porch!
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is AED 463
AED 1,000 total
includes taxes & fees
27 May - 28 May
CozyDen - AC, Grill, Bike to Mountain, Porch!
TV, offices

The Tower House | Hot Tub | Firepit | Dog-Friendly

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is AED 661
AED 2,403 total
includes taxes & fees
26 May - 27 May
The Tower House | Hot Tub | Firepit | Dog-Friendly
Property grounds

Large Killington Area Home | Sleeps 7 | Game Room

Large Killington Area Home | Sleeps 7 | Game Room
Bridgewater
9.6 out of 10, Exceptional, (7 reviews)
"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."
United States
Owen C.
The price is AED 698
AED 2,053 total
includes taxes & fees
26 May - 27 May
Large Killington Area Home | Sleeps 7 | Game Room
Terrace/patio

Classic Vermont Farmhouse near Sugarbush Resort

Classic Vermont Farmhouse near Sugarbush Resort
Warren
9.6 out of 10, Exceptional, (50 reviews)
"Great location for skiing at Sugarbush. Nice big living room for the whole group to gather. "
United States
Peggy V.
Classic Vermont Farmhouse near Sugarbush Resort
Smart TV, books

Cozy Moonship Yurt in the woods

Cozy Moonship Yurt in the woods
West Rutland
Cozy Moonship Yurt in the woods
Interior

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Rutland
10.0 out of 10, Exceptional, (4 reviews)
"House was clean, organized and spacious. Great location as well, close to grocery, gas and restaurants. Host answered questions quickly. "
United States
Dominic C.
The price is AED 701
AED 1,604 total
includes taxes & fees
27 May - 28 May
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
House, 6 Bedrooms | Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is AED 787
AED 2,909 total
includes taxes & fees
24 May - 25 May
Breakaway House by Killington Vacation Rentals
Exterior

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is AED 521
AED 2,165 total
includes taxes & fees
24 May - 25 May
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Interior

Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is AED 521
AED 2,165 total
includes taxes & fees
24 May - 25 May
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Indoor pool, a heated pool

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
The Woods
10.0 out of 10, Exceptional, (7 reviews)
"Location/proximity to Killington is awesome! A few minutes drive from the parkland lot at Ramshead. The community kept the roads and parking lots plowed well. Communication from the host was excellent. The condo was very comfortable for our family of 3 (2 adults and 4 yr old) and exactly as described. Great spot to relax after our days skiing! We would definitely come back!"
United States
Elizabeth C.
The price is AED 1,091
AED 2,334 total
includes taxes & fees
25 May - 26 May
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
Dining

large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.6 out of 10, Exceptional, (4 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AED 979
AED 2,170 total
includes taxes & fees
25 May - 26 May
large ski ranch hot tub close to killington pets ok
Smart TV, fireplace, video games, stereo

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Killington
10.0 out of 10, Exceptional, (19 reviews)
The price is AED 929
AED 2,432 total
includes taxes & fees
28 May - 29 May
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Fridge, microwave, oven, stovetop

Feel the real VT! Lakes, hikes, a foodies delight!

Feel the real VT! Lakes, hikes, a foodies delight!
Proctor
10.0 out of 10, Exceptional, (1 review)
"Clean and comfortable home. Plenty of space for our family! Great quiet neighborhood made it easy to relax on our trip."
United States
Rebecca
The price is AED 766
AED 2,246 total
includes taxes & fees
17 Jun - 18 Jun
Feel the real VT! Lakes, hikes, a foodies delight!
Smart TV, fireplace

Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole

Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
Killington
10.0 out of 10, Exceptional, (6 reviews)
"Such a great spot."
United States
Kathleen G.
Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
Smart TV

Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!

Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
Killington
Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
Fridge, microwave, oven, stovetop

CountryBear- AC, Pool, Hot Tub, Fire Pit, Grill

CountryBear- AC, Pool, Hot Tub, Fire Pit, Grill
Killington
10.0 out of 10, Exceptional, (31 reviews)
"Very nice and very rustic. The family enjoyed our time together at the Country Bear. "
United States
Robbie C.
The price is AED 1,087
AED 2,564 total
includes taxes & fees
25 May - 26 May
CountryBear- AC, Pool, Hot Tub, Fire Pit, Grill
TV, streaming services, music library, video library

Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Killington
7.0 out of 10, Good, (6 reviews)
"Excellent brief stay."
United States
Ron L.
The price is AED 566
AED 2,209 total
includes taxes & fees
24 May - 25 May
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
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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Top Pittsfield Hotel Reviews

Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"Great breakfast, quiet, safety, clean room, pleasant &friendly staff"
Elaine 1-night trip
Posted 1 day ago
Hampton Inn Rutland

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