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Compare 563 Vacation Homes in Stockbridge with updated reviews, rates, and availability.

New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b
Exterior

New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b

10.0 out of 10, Exceptional, (40)
"The owner was extremely easy to work with and even more responsive. The house has an AMAZING view Killington. Very clean and once you get the cast iron stove to temp it worked really well to heat the house. The sauna, and foosball table worked well. The hotub was easy to use, it fits 3 full size adults with no issue. The kitchen fridge had plenty of condiments, dressing and sauces. A really nice treat was that the beverage fridge was stocked with prev renters' drinks as well we added to it for...
New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Living area flooded with natural light.

BruinsDen - Ski On Ski Off (Home Stretch Trail)

9.8 out of 10, Exceptional, (10)
"Amazing. So clean. Room for everyone to spread out and enjoy their time."
The price is SAR 2,520
SAR 4,552 total
includes taxes & fees
25 Dec - 26 Dec
BruinsDen - Ski On Ski Off (Home Stretch Trail)
4 Season Secluded Lakefront Home near Ski Mountains

4 Season Secluded Lakefront Home near Ski Mountains

9.4 out of 10, Exceptional, (66)
"Beautiful spot..definitely a camp, very rustic. We enjoyed a canoe trip around the pond."
4 Season Secluded Lakefront Home near Ski Mountains
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

9.2 out of 10, Wonderful, (66)
"Best place to visit for fall leaf peeping! Very enjoyable experience "
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
Ski-in/out sunrise condo with pool & hot tub - great ski retreat

Ski-in/out sunrise condo with pool & hot tub - great ski retreat

8.8 out of 10, Excellent, (79)
"Property was nice and location was great even for an of season stay. Lots of fun close by like the killington adventure center & visiting small toes like Woodstock & ludlow. Also hiking close by!! We were a bit disappointed that the indoor pool & hot tub were closed until the peak winter season so may mention that in the listing. We loved having the fire place & sauna inside unit. "
Ski-in/out sunrise condo with pool & hot tub - great ski retreat
Killington, Vermont Ski House w/ Hot Tub and Sauna
I Our snow country home welcomes you!

Killington, Vermont Ski House w/ Hot Tub and Sauna

9.4 out of 10, Exceptional, (82)
"Perfect house. This is our second time there and we had a wonderful experience."
Killington, Vermont Ski House w/ Hot Tub and Sauna
Log manor on 65 private acres of land with entertaining amenities & hot tub

Log manor on 65 private acres of land with entertaining amenities & hot tub

9.8 out of 10, Exceptional, (6)
"Great property and beautiful views. Not too far from Killington. A wonderful trip to remember. Would definitely stay here again."
Log manor on 65 private acres of land with entertaining amenities & hot tub
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen
Living area

Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen

9.8 out of 10, Exceptional, (22)
"Great getaway with family. The home was very clean and well stocked with towels,linens, blankets, and most essentials. The first snowfall of the season made the Mountain Views picture perfect. Very close to Woodstock and Killington. "
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen
Valley View Retreat is a tastefully decorated home.
Living area

Valley View Retreat is a tastefully decorated home.

Valley View Retreat is a tastefully decorated home.
Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!
Exterior

Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Had a nice stay with friends at this beautiful house. Very spacious with plenty of beds and bathrooms. Spacious and very clean in quiet, peaceful location. Hosts quickly responded to any questions."
Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (18)
"Gorgeous property with everything that we needed! It was relaxing and comfortable for everyone. The kids had a blast! The property management team was great with communication and offered early check in and late check out. Would absolutely stay here again!"
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Lake

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (199)
"We had a wonderful 4 days/nights at Cozy Cottage. Perfectly named, well appointed decor and comfortable beds. Perfect for families. The fire pit, kayaks and conoe along with the string lights and sitting areas to watch the wood ducks and beaver family was the perfect way to decompress from the rat race."
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Beautifully renovated with fireplace and coffee bar
Enter the home to an open living space

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (87)
"Amazing, thank you!"
Beautifully renovated with fireplace and coffee bar
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Image from trailhead

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

9.8 out of 10, Exceptional, (52)
"This is our second stay at Joel’s condo. His improvements to the lower floor are very nice and made a lot of sense. We enjoyed the location and condo once again. Joel continues to be very thoughtful and helpful. A great place to get away, relax, and have fun. We also got some late season skiing in for those of us who enjoy the slopes."
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Custom-built Tiny House on forested lot near Quechee
House facade from driveway

Custom-built Tiny House on forested lot near Quechee

10.0 out of 10, Exceptional, (50)
"Everything was perfect and as advertised. Very easy to communicate with owner. No issues and offered a very private relaxing getaway. You’ll love it. Worth every penny. "
Custom-built Tiny House on forested lot near Quechee
Ski house 8 min from the mountain
Terrace/patio

Ski house 8 min from the mountain

9.8 out of 10, Exceptional, (15)
"Great time at this place gorgeous view and host was a pleasure to deal with. 👍👍"
Ski house 8 min from the mountain
Killington Vermont Ski and Snowmobiling House
Outside view

Killington Vermont Ski and Snowmobiling House

9.4 out of 10, Exceptional, (42)
"Good utilitarian property for fall leaf touring. Most everything worked ok, great for large family group but definitely not for someone desiring a fully furnished or decorated place. "
Killington Vermont Ski and Snowmobiling House
The Brandon Inn - King Room
Exterior

The Brandon Inn - King Room

8.4 out of 10, Very Good, (5)
"The Branford Inn was a historic hotel that despite its age was very nice."
The price is SAR 658
SAR 837 total
includes taxes & fees
25 Dec - 26 Dec
The Brandon Inn - King Room
Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee

Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee

9.4 out of 10, Exceptional, (41)
"Lovely place to enjoy Vermont. The condo was well located, clean, and the quechee club amenities were a lot of fun."
Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee
Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!
Welcome to your Ideal Killington Escape!

Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!

10.0 out of 10, Exceptional, (16)
"We had two families stay at the home the first week of April during Spring Break so we could do a couple of days of skiing. The house was wonderful. It had so many beds, which made it great for the 6 kids and then separate bedrooms for the two couples, which was great. We enjoyed making a fire in the fireplace at the end of the day as we played board games with the family..we especially enjoyed playing LCR (Left Center Right). Kristin's communication was incredible. She was always so quick to...
Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, 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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Other property types in Stockbridge

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (40)
"Like property— sad the lift that made it ski and in out was closed due weather conditions "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Loft for two with Hot Tub
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (222)
"We had the best time at Jeff’s perfect cozy ‘little loft’! It exceeded expectations! We especially enjoyed the hot tub after long days of skiing!"
Cozy Loft for two with Hot Tub
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
"The cabin was peaceful and everything was provided, plus some!" Stacy S

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (473)
"The cabin was amazing, the design and decor is perfect and the space is perfect. The hot tub and fire pit were so lovely in the evening, and the movie theatre was also excellent for watching TV and films. Jeff was an excellent host, super friendly and helpful and the area was lovely and quiet, very peaceful. Thanks again! "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
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.