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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

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 ￥15,705
￥38,378 total
includes taxes & fees
Apr 21 - Apr 22
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 ￥19,989
￥43,203 total
includes taxes & fees
Apr 21 - Apr 22
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 ￥28,555
￥103,793 total
includes taxes & fees
Apr 21 - Apr 22
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 ￥30,142
￥87,595 total
includes taxes & fees
Apr 21 - Apr 22
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 ￥26,820
￥88,832 total
includes taxes & fees
May 11 - May 12
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 ￥31,728
￥94,169 total
includes taxes & fees
Apr 23 - Apr 24
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 ￥40,136
￥105,048 total
includes taxes & fees
Apr 21 - Apr 22
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 ￥22,559
￥67,080 total
includes taxes & fees
Apr 23 - Apr 24
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 ￥30,600
￥120,836 total
includes taxes & fees
Apr 22 - Apr 23
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 ￥30,269
￥69,258 total
includes taxes & fees
Apr 23 - Apr 24
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 ￥31,728
￥59,522 total
includes taxes & fees
Apr 22 - Apr 23
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 ￥24,129
￥70,555 total
includes taxes & fees
Apr 26 - Apr 27
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 ￥47,103
￥100,788 total
includes taxes & fees
Apr 21 - Apr 22
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 ￥16,890
￥86,492 total
includes taxes & fees
Apr 21 - Apr 22
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 ￥16,890
￥86,492 total
includes taxes & fees
Apr 21 - Apr 22
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 ￥90,274
￥166,313 total
includes taxes & fees
May 4 - May 5
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 ￥55,841
￥140,721 total
includes taxes & fees
Apr 21 - Apr 22
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.
The price is ￥75,227
￥153,379 total
includes taxes & fees
Apr 21 - Apr 22
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 ￥37,756
￥82,864 total
includes taxes & fees
Apr 25 - Apr 26
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

On The River Inn

On The River Inn

10/10 Excellent
"A very nice property! We enjoyed the library lounge, the hot tub and sauna, as well as the grounds. This was a great experience all around. A lot went into the building and furnishings of this excellent hotel"
Graeme 2-night trip
Posted 11 hours ago
On The River Inn

Find out more about Pittsfield

Pittsfield Vacation Homes information

Number of reviews
147
Accommodation
578 Vacation Homes
Lowest Price
￥38,378
Highest Price
￥166,313