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Our top choices for Stockbridge vacation homes

Ski home/Pool Table Mountain Views near Killington/Woodstock

Stockbridge
10.0 out of 10, Exceptional, (2)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is AED 796
AED 2,514 total
includes taxes & fees
11 Dec - 12 Dec
Ski home/Pool Table Mountain Views near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock

Stockbridge
10.0 out of 10, Exceptional, (2)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is AED 820
AED 2,544 total
includes taxes & fees
14 Dec - 15 Dec
Ski Home/Arcade Mountain Views Near Killington/Woodstock

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

2.0 star property
Chelsea
10.0 out of 10, Exceptional, (37)
"Lovely farm and friendly hosts"
United States
Ruilin
The price is AED 441
AED 576 total
includes taxes & fees
16 Dec - 17 Dec
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Off Grid Glamping Shed with River Access

2.0 star property
Randolph
10.0 out of 10, Exceptional, (1)
The price is AED 215
AED 344 total
includes taxes & fees
12 Dec - 13 Dec
Off Grid Glamping Shed with River Access

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 AED 694
AED 2,048 total
includes taxes & fees
11 Dec - 12 Dec
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

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 AED 441
AED 1,206 total
includes taxes & fees
11 Dec - 12 Dec
Luxury Condo Tucked in the Heart of Killington

Mountain Stay | Skiing | Hiking | Sleeps 8

Bridgewater
9.6 out of 10, Exceptional, (7)
"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 AED 738
AED 2,032 total
includes taxes & fees
11 Dec - 12 Dec
Mountain Stay | Skiing | Hiking | Sleeps 8

Spacious country home, beautiful sunsets, 40 acres

Tunbridge
9.8 out of 10, Exceptional, (43)
"The accommodations were great with plenty of room. We all wanted to lay on the living room couches because they were so comfortable! The property was nice and peaceful with lots of flowers, bushes and trees to observe."
United States
Karen P.
The price is AED 459
AED 1,740 total
includes taxes & fees
15 Dec - 16 Dec
Spacious country home, beautiful sunsets, 40 acres

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Mt Holly
9.8 out of 10, Exceptional, (36)
"Wonderful cabin, well stocked, host was attentive and quick to address any questions."
United States
Eyal O.
The price is AED 1,339
AED 2,861 total
includes taxes & fees
24 Dec - 25 Dec
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

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 AED 583
AED 1,356 total
includes taxes & fees
16 Dec - 17 Dec
CozyDen-Location, Fireplace, Ski Off/Shuttle On!

Beautiful home located in the Mad River Valley

Warren
10.0 out of 10, Exceptional, (22)
"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

Warren
9.2 out of 10, Wonderful, (7)
"Good area"
United States
Dakota N.
Beautiful home located in the Mad River Valley

TheGrizz! Shuttle on/off!

Killington
10.0 out of 10, Exceptional, (4)
"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 AED 710
AED 1,989 total
includes taxes & fees
14 Dec - 15 Dec
TheGrizz! Shuttle on/off!

Mad Mountain Meadows - Stunning Mountain Views!

East Warren
10.0 out of 10, Exceptional, (3)
"Great house great location!"
United States
Elizabeth D.
The price is AED 483
AED 2,257 total
includes taxes & fees
11 Dec - 12 Dec
Mad Mountain Meadows - Stunning Mountain Views!

Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

Pomfret
10.0 out of 10, Exceptional, (4)
"Enjoyed the cleanliness and the convenience of being close to Woodstock, and not too far from Stowe."
United States
Dee Dee H.
The price is AED 735
AED 1,633 total
includes taxes & fees
11 Dec - 12 Dec
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

large ski ranch hot tub close to killington pets ok

2.0 star property
Mendon
10.0 out of 10, Exceptional, (1)
"Amazing stay! Gorgeous house, clean, perfect location. The host was super responsive and made the check in check out process so easy.Highly reccomend and can’t wait to stay again next year. "
United States
Nicole H.
The price is AED 752
AED 1,879 total
includes taxes & fees
11 Dec - 12 Dec
large ski ranch hot tub close to killington pets ok

Bob's Sled Lodge 2 Bedroom Home

3.0 star property
North Sherburne
The price is AED 531
AED 1,995 total
includes taxes & fees
11 Dec - 12 Dec
Bob's Sled Lodge 2 Bedroom Home

Whitetail Chalet at Killington: 4BR/2BA

2.0 star property
Killington
10.0 out of 10, Exceptional, (2)
"A beautiful property which is very well equipped and really well kept. Great communication and wish we could have stayed longer. "
United Kingdom
John P.
The price is AED 869
AED 2,673 total
includes taxes & fees
11 Dec - 12 Dec
Whitetail Chalet at Killington: 4BR/2BA

Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.

2.0 star property
Killington
10.0 out of 10, Exceptional, (2)
"This was a perfect property for our quick vacation. The house is very well equipped and you have everything you need for a relaxing fun stay in Killington. The hot tub was great, and the house is in a very convenient location while fairly private at the same time. We really enjoyed our stay and would definitely recommend staying here."
United States
Linda D.
The price is AED 735
AED 2,366 total
includes taxes & fees
11 Dec - 12 Dec
Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.

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 AED 727
AED 2,475 total
includes taxes & fees
11 Dec - 12 Dec
4BR Killington Home Perfect for Families, Pet-Friendly
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 Stockbridge Hotel Reviews