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Our top choices for Pittsfield vacation 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 ¥30,003
¥99,569 total
includes taxes & fees
Jan 20 - Jan 21
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
2.0 star property
North Sherburne
The price is ¥29,458
¥96,450 total
includes taxes & fees
Jan 20 - Jan 21
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!
Pittsfield
The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

Off Grid Glamping Shed with River Access

Off Grid Glamping Shed with River Access
2.0 star property
Randolph
10.0 out of 10, Exceptional, (1 review)
The price is ¥9,250
¥14,789 total
includes taxes & fees
Jan 20 - Jan 21
Off Grid Glamping Shed with River Access

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 ¥25,615
¥59,141 total
includes taxes & fees
Jan 27 - Jan 28
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 ¥30,992
¥57,910 total
includes taxes & fees
Jan 20 - Jan 21
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

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

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

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 ¥30,517
¥89,078 total
includes taxes & fees
Jan 21 - Jan 22
Blueberry Hill Escape | Pet Friendly | HotTub | AC

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 ¥40,795
¥97,933 total
includes taxes & fees
Jan 27 - Jan 28
Large Killington Area Home | Sleeps 7 | Game Room

Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
8.0 out of 10, Very Good, (1 review)
"The condo was in a beautiful location but was rather isolated from grocery and dining options. Our host was good at communicating however we received a message about the fireplace not being available to us a day before we came and we got there in the dark with no lights on. The condo itself could not really be called "luxury" as it was dated and lacked some basics like soap in the bathroom, a towel hook in the 1/2 bath, kleenex, cracked dishes, etc. Liked that it was near a waterfall and hiking...
United States
Dean
The price is ¥26,374
¥60,939 total
includes taxes & fees
Jan 27 - Jan 28
Luxury Condo Tucked in the Heart of Killington

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 ¥22,015
¥65,302 total
includes taxes & fees
Feb 1 - Feb 2
Killington Retreat | Deck-Fire Pit-Mountain Views!

The Bomoseen Bungalow: Vermont Lake House with Private Dock

The Bomoseen Bungalow: Vermont Lake House with Private Dock
2.0 star property
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 ¥27,094
¥87,471 total
includes taxes & fees
Jan 20 - Jan 21
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
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

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

Vermont Retreat: 3BR with Mountain Views and Trails

Vermont Retreat: 3BR with Mountain Views and Trails
2.0 star property
Brookfield
The price is ¥31,624
¥93,329 total
includes taxes & fees
Jan 22 - Jan 23
Vermont Retreat: 3BR with Mountain Views and Trails

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
2.0 star property
Killington
The price is ¥23,093
¥71,176 total
includes taxes & fees
Jan 20 - Jan 21
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Secluded Mountain Getaway with Hot tub and Views!

Secluded Mountain Getaway with Hot tub and Views!
Granville
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place & convenient to Sugarbush & Rochester.We had 10 guys mountain biking in the area and worked out perfectly."
United States
Clint F.
The price is ¥25,483
¥110,359 total
includes taxes & fees
Jan 21 - Jan 22
Secluded Mountain Getaway with Hot tub and Views!

4BR Killington Home Perfect for Families, Pet-Friendly

4BR Killington Home Perfect for Families, Pet-Friendly
2.0 star property
North Sherburne
10.0 out of 10, Exceptional, (22 reviews)
"Spacious, clean and cozy home. Perfect for a ski trip or weekend getaway."
United States
Darko G.
The price is ¥40,914
¥119,836 total
includes taxes & fees
Jan 20 - Jan 21
4BR Killington Home Perfect for Families, Pet-Friendly

Bob's Sled Lodge 2 Bedroom Home

Bob's Sled Lodge 2 Bedroom Home
3.0 star property
North Sherburne
Bob's Sled Lodge 2 Bedroom Home
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

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Pittsfield Vacation Homes information

Number of reviews
130
Accommodation
559 Vacation Homes
Lowest Price
¥14,789
Highest Price
¥119,836