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Our top choices for Pittsfield holiday homes

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...
United States
Essa R.
The price is HK$1,479
HK$4,866 total
includes taxes & fees
26 Jan - 27 Jan
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
North Sherburne
The price is HK$1,488
HK$4,763 total
includes taxes & fees
26 Jan - 27 Jan
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

Off Grid Glamping Shed with River Access

Off Grid Glamping Shed with River Access
Randolph
10.0 out of 10, Exceptional, (1 review)
The price is HK$456
HK$729 total
includes taxes & fees
26 Jan - 27 Jan
Off Grid Glamping Shed with River Access

Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Comfortable stay, great location. "
United States
Marjana
The price is HK$1,207
HK$2,883 total
includes taxes & fees
27 Jan - 28 Jan
Luxury Condo Tucked in the Heart of Killington

CozyDen-Location, Fireplace, Ski Off/Shuttle On!

CozyDen-Location, Fireplace, Ski Off/Shuttle On!
Killington
10.0 out of 10, Exceptional, (1 review)
"Very quiet and private feeling even though it is in a condo like setting. Very clean, and had all the conveniences we needed (A/C, coffee maker, full kitchen appliances). And so kind and personal to leave some souvenirs of the area. We felt very comfortable when every we finished our day of sightseeing to come back to our home away from home. "
United States
denise k.
The price is HK$943
HK$2,511 total
includes taxes & fees
27 Jan - 28 Jan
CozyDen-Location, Fireplace, Ski Off/Shuttle On!

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 HK$1,302
HK$2,550 total
includes taxes & fees
28 Jan - 29 Jan
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

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 HK$2,012
HK$4,855 total
includes taxes & fees
27 Jan - 28 Jan
Large Killington Area Home | Sleeps 7 | Game Room

Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.0 out of 10, Wonderful, (4 reviews)
"This place is a perfect rustic getaway with easy convenience to town. The host was great. Spacious and super relaxing with nice view out back. "
United States
Thaddeus T.
The price is HK$1,053
HK$3,057 total
includes taxes & fees
1 Feb - 2 Feb
Killington Retreat | Deck-Fire Pit-Mountain Views!

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
Killington
10.0 out of 10, Exceptional, (1 review)
"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "
United States
Catherine S.
The price is HK$1,506
HK$4,942 total
includes taxes & fees
26 Jan - 27 Jan
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.6 out of 10, Exceptional, (40 reviews)
"The place was spacious, but small, which I loved! Plenty of hot water, great communication with owner, plenty of extra chairs and the leaf for the table was fantastic!"
United States
Michael M.
Beautiful home located in the Mad River Valley

The Bomoseen Bungalow: Vermont Lake House with Private Dock

The Bomoseen Bungalow: Vermont Lake House with Private Dock
Bomoseen
9.6 out of 10, Exceptional, (4 reviews)
"Nice place to stay. Very well equipped and clean."
United States
Rich S.
The price is HK$1,336
HK$4,313 total
includes taxes & fees
26 Jan - 27 Jan
The Bomoseen Bungalow: Vermont Lake House with Private Dock

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.4 out of 10, Exceptional, (8 reviews)
"Good area"
United States
Dakota N.
Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
10.0 out of 10, Exceptional, (23 reviews)
"Fantastic house in a beautiful setting. Just right for the area and the kind of trip we were hoping to have. Colin is a great host as well."
United States
kevin m.
Beautiful home located in the Mad River Valley

Vermont Retreat: 3BR with Mountain Views and Trails

Vermont Retreat: 3BR with Mountain Views and Trails
Brookfield
The price is HK$1,559
HK$4,628 total
includes taxes & fees
17 Feb - 18 Feb
Vermont Retreat: 3BR with Mountain Views and Trails

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

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Rutland
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,488
HK$3,290 total
includes taxes & fees
2 Feb - 3 Feb
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

The Mountainside House - Luxury Home in Killington

The Mountainside House - Luxury Home in Killington
Killington
9.6 out of 10, Exceptional, (55 reviews)
"Had a great stay as usual for our company trip!"
United States
Anonymous traveller
The Mountainside House - Luxury Home in Killington

Blueberry Hill Escape | Pet Friendly | HotTub | AC

Blueberry Hill Escape | Pet Friendly | HotTub | AC
Bridgewater
9.6 out of 10, Exceptional, (17 reviews)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is HK$2,043
HK$5,048 total
includes taxes & fees
11 Feb - 12 Feb
Blueberry Hill Escape | Pet Friendly | HotTub | AC

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, (2 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is HK$1,284
HK$4,855 total
includes taxes & fees
27 Jan - 28 Jan
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (2 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is HK$1,284
HK$4,855 total
includes taxes & fees
27 Jan - 28 Jan
Ski Home/Arcade Mountain Views Near Killington/Woodstock

TheGrizz! Shuttle on/off!

TheGrizz! Shuttle on/off!
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 HK$1,928
HK$4,769 total
includes taxes & fees
2 Feb - 3 Feb
TheGrizz! Shuttle on/off!
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

Find out more about Pittsfield

Pittsfield Vacation Homes information

Number of reviews
128
Accommodation
559 Vacation Homes
Lowest Price
HK$729
Highest Price
HK$5,048

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