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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Pittsfield vacation homes

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
19 Apr - 20 Apr
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
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
21 Apr - 22 Apr
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
21 Apr - 22 Apr
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 2,032 total
includes taxes & fees
19 Apr - 20 Apr
Large Killington Area Home | Sleeps 7 | Game Room
Fridge, microwave, oven, stovetop

Feel the real VT! Ski Killington and a foodie’s delight!

Feel the real VT! Ski Killington and a foodie’s 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 621
AED 2,057 total
includes taxes & fees
11 May - 12 May
Feel the real VT! Ski Killington and a foodie’s delight!
Interior

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.6 out of 10, Exceptional, (43 reviews)
"Very convenient to Warren center. This house served us well as we were able to bring our dog over the Christmas holiday. Perfect house for a family. "
United States
Monica R.
Beautiful home located in the Mad River Valley
Interior

Vermont Retreat: 3BR with Mountain Views and Trails

Vermont Retreat: 3BR with Mountain Views and Trails
Brookfield
The price is AED 735
AED 2,180 total
includes taxes & fees
20 Apr - 21 Apr
Vermont Retreat: 3BR with Mountain Views and Trails
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)
"Great location and excellent hosts "
United States
Peter G.
The price is AED 929
AED 2,432 total
includes taxes & fees
19 Apr - 20 Apr
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Golf

The Grizz- AC, Pool, Sauna, Gym, Near Resort

The Grizz- AC, Pool, Sauna, Gym, Near Resort
Killington
10.0 out of 10, Exceptional, (4 reviews)
"Place was overall great and just as advertised. Beds were awesome including the Murphy bed. Thanks for a wonderful weekend! I would definitely stay again. "
United States
Angela S.
The price is AED 542
AED 1,580 total
includes taxes & fees
19 Apr - 20 Apr
The Grizz- AC, Pool, Sauna, Gym, Near Resort
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 732
AED 2,831 total
includes taxes & fees
19 Apr - 20 Apr
Breakaway House by Killington Vacation Rentals
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
19 Apr - 20 Apr
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Living area

Cozy Moonship Yurt in the woods

Cozy Moonship Yurt in the woods
West Rutland
The price is AED 735
AED 1,370 total
includes taxes & fees
29 Apr - 30 Apr
Cozy Moonship Yurt in the woods
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 658
AED 1,761 total
includes taxes & fees
23 Apr - 24 Apr
large ski ranch hot tub close to killington pets ok
Smart TV, fireplace

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 1,114
AED 2,365 total
includes taxes & fees
26 Apr - 27 Apr
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
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 489
AED 2,129 total
includes taxes & fees
19 Apr - 20 Apr
Ski Home/Arcade Mountain Views Near Killington/Woodstock
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 391
AED 2,007 total
includes taxes & fees
19 Apr - 20 Apr
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Interior

Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace

Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace
Hancock
10.0 out of 10, Exceptional, (1 review)
"The maple castle was awesome! Definitely the most unique house I have ever stayed in. You can sit in the hot tub and watch the river or you can walk down a tiny hill to tie up a tube and float in it. The owners were extremely helpful and responsive. Would definitely recommend. "
United States
Katie H.
The price is AED 2,200
AED 3,990 total
includes taxes & fees
4 May - 5 May
Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace
Exterior

Royalbear-AC, Hot Tub, Grill, FirePit, Gameroom

Royalbear-AC, Hot Tub, Grill, FirePit, Gameroom
Killington
10.0 out of 10, Exceptional, (24 reviews)
"Great house and location, and responsive hosts. Loved it, def will stay again."
United States
Max P.
The price is AED 1,293
AED 3,258 total
includes taxes & fees
20 Apr - 21 Apr
Royalbear-AC, Hot Tub, Grill, FirePit, Gameroom
Fridge, microwave, oven, stovetop

BruinsDen- Hot Tub, Fooseball, Mountain Views

BruinsDen- Hot Tub, Fooseball, Mountain Views
Killington
9.8 out of 10, Exceptional, (20 reviews)
"We loved our stay, felt like home away from home. A perfect place to relax after a day on the slopes. Grateful for our time there. #recommend!"
United States
Jennifer C.
BruinsDen- Hot Tub, Fooseball, Mountain Views
Outdoor spa tub

Walk to Pickle Barrel & Jax. Hot tub & Views

Walk to Pickle Barrel & Jax. Hot tub & Views
Killington
10.0 out of 10, Exceptional, (7 reviews)
"Great hosts with a great location to Killington"
United States
Ed P.
The price is AED 915
AED 1,967 total
includes taxes & fees
25 Apr - 26 Apr
Walk to Pickle Barrel & Jax. Hot tub & Views
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

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"awesome place! Distillery was awesome, the pool was clean, great room and friendly staff. Had an excellent stay"
Brooke 1-night trip
Posted 8 hours ago
The Mountain Inn at Killington

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