Holiday Homes in Pittsfield

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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 holiday 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 NZ$405
includes taxes & fees
19 Apr - 20 Apr
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
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 NZ$1,083
includes taxes & fees
22 Apr - 23 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 NZ$924
includes taxes & fees
22 Apr - 23 Apr
Large Killington Area Home | Sleeps 7 | Game Room
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 NZ$455
includes taxes & fees
22 Apr - 23 Apr
CozyDen - AC, Grill, Bike to Mountain, Porch!
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 NZ$903
includes taxes & fees
11 May - 12 May
Feel the real VT! Ski Killington and a foodie’s delight!
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 NZ$726
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 NZ$627
includes taxes & fees
28 Apr - 29 Apr
Cozy Moonship Yurt in the woods
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 NZ$1,096
includes taxes & fees
22 Apr - 23 Apr
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Exterior

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
10.0 out of 10, Exceptional, (24 reviews)
"Had a wonderful stay "
United States
Yang O.
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 NZ$996
includes taxes & fees
19 Apr - 20 Apr
Vermont Retreat: 3BR with Mountain Views and Trails
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 NZ$1,303
includes taxes & fees
20 Apr - 21 Apr
Breakaway House by Killington Vacation Rentals
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 NZ$712
includes taxes & fees
22 Apr - 23 Apr
The Grizz- AC, Pool, Sauna, Gym, Near Resort
Microwave, oven, stovetop, dishwasher

Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
The price is NZ$1,054
includes taxes & fees
20 Apr - 21 Apr
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
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)
"House was great. Unique farmhouse feel. Family had a blast. "
United States
Shane C.
The price is NZ$1,194
includes taxes & fees
19 Apr - 20 Apr
CountryBear- AC, Pool, Hot Tub, Fire Pit, Grill
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 NZ$797
includes taxes & fees
23 Apr - 24 Apr
large ski ranch hot tub close to killington pets ok
Living area

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
The price is NZ$1,327
includes taxes & fees
1 May - 2 May
Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
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 NZ$1,793
includes taxes & fees
4 May - 5 May
Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace
Exterior

BearRight- AC, Pool, Hot Tub, Grill, FirePit

BearRight- AC, Pool, Hot Tub, Grill, FirePit
Killington
9.8 out of 10, Exceptional, (12 reviews)
"Excellent stay, very accommodating hosts. Well organized"
United States
Brian S.
The price is NZ$1,369
includes taxes & fees
18 Apr - 19 Apr
BearRight- AC, Pool, Hot Tub, Grill, FirePit
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.
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
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 NZ$1,070
includes taxes & fees
18 Apr - 19 Apr
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
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

6/10 Okay
"Night staff was very very nice. Comfortable bed and clean room. TV didn't work unfortunately."
Megan 1-night trip
Posted 15 hours ago
On The River Inn

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
126
Accommodation
559 Holiday Homes
Lowest Price
NZ$405
Highest Price
NZ$1,793