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Vacation Homes in Pittsfield

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

Pittsfield
The price is SAR 1,238
SAR 3,096 total
includes taxes & fees
24 Nov - 25 Nov
The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

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

North Sherburne
10.0 out of 10, Exceptional, (1)
"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 SAR 693
SAR 2,109 total
includes taxes & fees
24 Nov - 25 Nov
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

The Getaway 4 Bedroom Home

3.0 star property
Pittsfield
The price is SAR 1,543
SAR 3,566 total
includes taxes & fees
24 Nov - 25 Nov
The Getaway 4 Bedroom Home

Alpine Chalet, Fireplace, Pool, Gym, At Pico.

2.0 star property
Killington
10.0 out of 10, Exceptional, (5)
"Such a great spot."
United States
Kathleen G.
The price is SAR 1,135
SAR 3,146 total
includes taxes & fees
2 Dec - 3 Dec
Alpine Chalet, Fireplace, Pool, Gym, At Pico.

4BR Killington Home Perfect for Families, Pet-Friendly

2.0 star property
North Sherburne
10.0 out of 10, Exceptional, (22)
"Spacious, clean and cozy home. Perfect for a ski trip or weekend getaway."
United States
Darko G.
The price is SAR 743
SAR 2,557 total
includes taxes & fees
24 Nov - 25 Nov
4BR Killington Home Perfect for Families, Pet-Friendly

Spacious country home, beautiful sunsets, 40 acres

Tunbridge
9.8 out of 10, Exceptional, (42)
"Awsome place to stay for a week! "
United States
Melinda G.
The price is SAR 525
SAR 1,798 total
includes taxes & fees
23 Nov - 24 Nov
Spacious country home, beautiful sunsets, 40 acres

Luxury Condo Tucked in the Heart of Killington

Killington
8.0 out of 10, Very Good, (1)
"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 SAR 446
SAR 1,214 total
includes taxes & fees
23 Nov - 24 Nov
Luxury Condo Tucked in the Heart of Killington

MT Holly Ski/lake house hideaway(Avail. Daily, weekends & seasonally Dec-April)

Mount Holly
9.8 out of 10, Exceptional, (20)
"Everything was as expected. Very clean, great location. Would stay again!"
United States
Jenna K.
The price is SAR 1,009
SAR 1,987 total
includes taxes & fees
1 Dec - 2 Dec
MT Holly Ski/lake house hideaway(Avail. Daily, weekends & seasonally Dec-April)

A charming 1820's farmhouse

Woodstock
10.0 out of 10, Exceptional, (29)
"Excellent accommodations! One of the best VRBO’s I’ve ever stayed in. There were 5 women traveling together for a long weekend and Carmen’s place was just the ticket with our own bedrooms and en suite bathrooms. We had the entire place to ourselves and felt very spoiled."
United States
kelly f.
The price is SAR 3,390
SAR 5,493 total
includes taxes & fees
4 Dec - 5 Dec
A charming 1820's farmhouse

2 miles to ski lifts, 6 BR, 3BA hot tub,yard, AC, grill, lux bedding. CEDARWALK

Killington
10.0 out of 10, Exceptional, (62)
"Beautiful, modern home, immaculate, great layout, comfortable beds, hot tub was perfect, near Town of Woodstock and Ski Area. Can't imagine a better place to stay!"
United States
Howard K.
The price is SAR 6,938
SAR 10,311 total
includes taxes & fees
26 Nov - 27 Nov
2 miles to ski lifts, 6 BR, 3BA hot tub,yard, AC, grill, lux bedding. CEDARWALK

Beautiful home located in the Mad River Valley

Warren
9.8 out of 10, Exceptional, (39)
"We had a great time staying at this house during our Sugarbush skiing trip this February. The place is easy to access and is close to the ski resort. The house had everything we needed for a comfortable stay. I highly recommend this rental."
United States
Dmitriy K.
Beautiful home located in the Mad River Valley

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Bridgewater
9.6 out of 10, Exceptional, (17)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is SAR 514
SAR 1,844 total
includes taxes & fees
23 Nov - 24 Nov
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

Killington
9.6 out of 10, Exceptional, (64)
"We enjoyed the stay. The house was comfortable. Best hot tub we have had in a rental. Location is great."
United States
Cheryl K.
The price is SAR 1,093
SAR 3,636 total
includes taxes & fees
24 Nov - 25 Nov
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

The Bomoseen Bungalow: Vermont Lake House with Private Dock

2.0 star property
Bomoseen
9.6 out of 10, Exceptional, (4)
"Nice place to stay. Very well equipped and clean."
United States
Rich S.
The price is SAR 631
SAR 2,053 total
includes taxes & fees
24 Nov - 25 Nov
The Bomoseen Bungalow: Vermont Lake House with Private Dock

SlopeSide Chalet- Ski to and from your home

Killington
10.0 out of 10, Exceptional, (17)
"Clean, comfortable, relaxing; we didnt want to leave!"
United States
Karen M.
The price is SAR 2,143
SAR 4,376 total
includes taxes & fees
25 Nov - 26 Nov
SlopeSide Chalet- Ski to and from your home

5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

granville
9.4 out of 10, Exceptional, (83)
"Great place! Comfortable and conveniently located. "
United States
Violet R.
The price is SAR 338
SAR 1,138 total
includes taxes & fees
23 Nov - 24 Nov
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

DoubleDen - Duplex, Sleeps 16, Hot Tub.

Killington
10.0 out of 10, Exceptional, (21)
"Perfect location, easy access to everything, and plenty of space for big groups"
United States
Stas T.
The price is SAR 1,296
SAR 3,791 total
includes taxes & fees
24 Nov - 25 Nov
DoubleDen - Duplex, Sleeps 16, Hot Tub.

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

Killington
10.0 out of 10, Exceptional, (1)
"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 SAR 352
SAR 1,081 total
includes taxes & fees
25 Nov - 26 Nov
CozyDen-Location, Fireplace, Ski Off/Shuttle On!

Beautiful home located in the Mad River Valley

Warren
10.0 out of 10, Exceptional, (22)
"Had a wonderful stay "
United States
Yang O.
Beautiful home located in the Mad River Valley

BruinsDen- Fooseball, Hot Tub, Mountain Views

Killington
9.6 out of 10, Exceptional, (14)
"Amazing. So clean. Room for everyone to spread out and enjoy their time."
United States
Julianne W.
The price is SAR 992
SAR 3,012 total
includes taxes & fees
2 Dec - 3 Dec
BruinsDen- Fooseball, Hot Tub, Mountain 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