Search Vacation Homes in Stockbridge

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Stockbridge vacation homes

Property grounds
Ski home/Pool Table Mountain Views near Killington/Woodstock

Vacation Home in Stockbridge

Ski home/Pool Table Mountain Views near Killington/Woodstock
10.0 out of 10, Exceptional, (2)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
$604 nightly
The price is $677
Dec 15 - Dec 16
Total with taxes and fees
Ski home/Pool Table Mountain Views near Killington/Woodstock
Terrace/patio
Ski Home/Arcade Mountain Views Near Killington/Woodstock

Vacation Home in Stockbridge

Ski Home/Arcade Mountain Views Near Killington/Woodstock
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.
$604 nightly
The price is $677
Dec 15 - Dec 16
Total with taxes and fees
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Property grounds
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Vacation Home in Chelsea

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
2.0 star property
10.0 out of 10, Exceptional, (37)
"Lovely farm and friendly hosts"
United States
Ruilin
$140 nightly
The price is $157
Dec 17 - Dec 18
Total with taxes and fees
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Property grounds
Off Grid Glamping Shed with River Access

Vacation Home in Randolph

Off Grid Glamping Shed with River Access
2.0 star property
10.0 out of 10, Exceptional, (1)
$84 nightly
The price is $94
Dec 11 - Dec 12
Total with taxes and fees
Off Grid Glamping Shed with River Access
Terrace/patio
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Vacation Home in Bridgewater

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
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.
$498 nightly
The price is $558
Dec 11 - Dec 12
Total with taxes and fees
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Fridge, microwave, oven, stovetop
Luxury Condo Tucked in the Heart of Killington

Vacation Home in Killington

Luxury Condo Tucked in the Heart of 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
$309 nightly
The price is $328
Dec 14 - Dec 15
Total with taxes and fees
Luxury Condo Tucked in the Heart of Killington
Fridge, microwave, oven, stovetop
Mountain Stay | Skiing | Hiking | Sleeps 8

Vacation Home in Bridgewater

Mountain Stay | Skiing | Hiking | Sleeps 8
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.
$494 nightly
The price is $553
Dec 11 - Dec 12
Total with taxes and fees
Mountain Stay | Skiing | Hiking | Sleeps 8
Exterior
Spacious country home, beautiful sunsets, 40 acres

Vacation Home in Tunbridge

Spacious country home, beautiful sunsets, 40 acres
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.
$423 nightly
The price is $474
Dec 15 - Dec 16
Total with taxes and fees
Spacious country home, beautiful sunsets, 40 acres
Fridge, microwave, oven, stovetop
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Vacation Home in Mt Holly

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
9.8 out of 10, Exceptional, (36)
"Wonderful cabin, well stocked, host was attentive and quick to address any questions."
United States
Eyal O.
$436 nightly
The price is $488
Dec 11 - Dec 12
Total with taxes and fees
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Fridge, microwave, oven, stovetop
CozyDen-Location, Fireplace, Ski Off/Shuttle On!

Vacation Home in Killington

CozyDen-Location, Fireplace, Ski Off/Shuttle On!
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.
$326 nightly
The price is $368
Dec 16 - Dec 17
Total with taxes and fees
CozyDen-Location, Fireplace, Ski Off/Shuttle On!
Property grounds
Beautiful home located in the Mad River Valley

Vacation Home in Warren

Beautiful home located in the Mad River Valley
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
Property grounds
Beautiful home located in the Mad River Valley

Vacation Home in Warren

Beautiful home located in the Mad River Valley
9.2 out of 10, Wonderful, (7)
"Good area"
United States
Dakota N.
Beautiful home located in the Mad River Valley
Golf
TheGrizz! Shuttle on/off!

Vacation Home in Killington

TheGrizz! Shuttle on/off!
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.
$479 nightly
The price is $542
Dec 14 - Dec 15
Total with taxes and fees
TheGrizz! Shuttle on/off!
Interior
Mad Mountain Meadows - Stunning Mountain Views!

Vacation Home in East Warren

Mad Mountain Meadows - Stunning Mountain Views!
10.0 out of 10, Exceptional, (3)
"Great house great location!"
United States
Elizabeth D.
$549 nightly
The price is $614
Dec 11 - Dec 12
Total with taxes and fees
Mad Mountain Meadows - Stunning Mountain Views!
Interior
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

Vacation Home in Pomfret

Peaceful oasis, stunning views, less than 10 mins from Woodstock Village
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.
$396 nightly
The price is $444
Dec 11 - Dec 12
Total with taxes and fees
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village
Spa
large ski ranch hot tub close to killington pets ok

Vacation Home in Mendon

large ski ranch hot tub close to killington pets ok
2.0 star property
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.
$457 nightly
The price is $512
Dec 11 - Dec 12
Total with taxes and fees
large ski ranch hot tub close to killington pets ok
House, 2 Bedrooms | Exterior
Bob's Sled Lodge 2 Bedroom Home

Vacation Home in North Sherburne

Bob's Sled Lodge 2 Bedroom Home
3.0 star property
$492 nightly
The price is $546
Dec 11 - Dec 12
Total with taxes and fees
Bob's Sled Lodge 2 Bedroom Home
Outdoor spa tub
Whitetail Chalet at Killington: 4BR/2BA

Vacation Home in Killington

Whitetail Chalet at Killington: 4BR/2BA
2.0 star property
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.
$643 nightly
The price is $726
Dec 11 - Dec 12
Total with taxes and fees
Whitetail Chalet at Killington: 4BR/2BA
Outdoor spa tub
Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.

Vacation Home in Killington

Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.
2.0 star property
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.
$570 nightly
The price is $644
Dec 11 - Dec 12
Total with taxes and fees
Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.
Dining
4BR Killington Home Perfect for Families, Pet-Friendly

Vacation Home in North Sherburne

4BR Killington Home Perfect for Families, Pet-Friendly
2.0 star property
10.0 out of 10, Exceptional, (22)
"Spacious, clean and cozy home. Perfect for a ski trip or weekend getaway."
United States
Darko G.
$596 nightly
The price is $674
Dec 11 - Dec 12
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stockbridge Hotel Reviews

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"We stopped at this hotel on our way up to Stowe Mountain traveling from NJ. The room was affordable, modern, & clean. Our hotel room was a pleasant surprise. We had a full size fridge, microwave, oven, & kitchen in there. We stayed in a hearing impaired room that had a very spacious bathroom. We didn’t notice a lot of food options other than a McDonalds and convenience store about half a mile away. The lobby had a lot of amenities like snacks and other items you may have forgot to pack but were on the pricey side (ex. A bottle of Diet Coke was $4). We would definitely stay again."
Ellen M 1-night trip
Posted 3 days ago
My Place Hotel-Randolph VT

Find out more about Stockbridge

Stockbridge Vacation Homes information

Number of reviews
171
Accommodation
672 Vacation Homes
Lowest Price
$94
Highest Price
$726

Explore a world of travel with Expedia