Holiday Homes in Stockbridge

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Featured Holiday Homes in Stockbridge

Spacious country home, beautiful sunsets, 40 acres
9.8 out of 10, Exceptional, (24)
"We stayed at the house for a family wedding. It was a perfect place for our family. "
Spacious country home, beautiful sunsets, 40 acres
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
10.0 out of 10, Exceptional, (93)
"My wife, adult daughter and my wife's parents planned this trip for several months for a leaf tour outside of our home state of PA. We never have visited VT. But have tons of friends that have and recommended a few spots. We wanted to find a spot that would accommodate our 80+ year old parents and their walking limitations and allow us the opportunity to comfortably stay in for the night should we need a break . The location provided a great home-base for our meandering around the state. ...
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
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
Spectacular 4 Bed Killington Home
9.8 out of 10, Exceptional, (108)
"Great home, abundant firewood, lighting far better than the usual VRBO, lots of cookware, and kind owner. We had an excellent time!"
Spectacular 4 Bed Killington Home
Slopeside Chalet - Ski to and from your home!
10.0 out of 10, Exceptional, (9)
"Exceeded my expectations - luxury bedding - condo felt homey and just smelled good! Hosts very responsive! Best Topridge experience we’ve had"
The price is AU$1,115
includes taxes & fees
17 Nov - 18 Nov
Slopeside Chalet - Ski to and from your home!
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!
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
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
9.2 out of 10, Wonderful, (65)
"Best place to visit for fall leaf peeping! Very enjoyable experience "
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
Luxurious guest home with private art gallery in the heart of a historic village
10.0 out of 10, Exceptional, (13)
"Absolutely unique and amazing experience staying here. Space is gorgeously appointed and impeccably clean. Walk out the door right into a cute town with all the amenities right there. Edward was the perfect host: attentive to detail, communicative and pleasant. We will definitely stay here again if in the area! "
Luxurious guest home with private art gallery in the heart of a historic village
Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, (82)
"We had a wonderful 4 night stay at this Vermont condo. Wanda and Eran were great hosts. The condo was very nice and wonderfully decorated just like we imagined it would be. We loved the coffee bar and they even left us some wonderful cookies. They go above and beyond to make your vacation special. We loved how close the condo is to quechee village and vins which our 1 year old loved. We also made a stop in Waterbury Stowe Vermont and shelburne Vermont for cold hollow cider, Ben and Jerry’s, the...
Beautifully renovated with fireplace and coffee bar
Custom-built Tiny House on forested lot near Quechee
10.0 out of 10, Exceptional, (48)
"Great location, property was beautiful! "
Custom-built Tiny House on forested lot near Quechee
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
8.8 out of 10, Excellent, (18)
"Very cute cabin in the woods. Less than 2 miles off of route 4, which made it easy to get anywhere in Vermont!"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
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 AU$308
includes taxes & fees
18 Nov - 19 Nov
The Brandon Inn - King Room
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
10.0 out of 10, Exceptional, (63)
"This house was perfect for our group of twelve. We were three families with kids ranging in ages from 6-14yrs old. There was enough space for everyone to relax after a day of skiing. The kitchen was very well stocked and had everything we needed. The ski hill is only a 5 mins drive. We would definitely stay here again"
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
New! 4BR/3.5 BR luxurious escape to Quechee with large private yard
10.0 out of 10, Exceptional, (1)
"The house was perfect for our family of five and was everything that was advertised. We had clear instructions on how to work everything and the setting was perfect. Private yet close to everything that you needed to access in Quechee and Woodstock. 5 Star for sure!"
New! 4BR/3.5 BR luxurious escape to Quechee with large private yard
Private Mountain View minutes to Hiking, biking, golfing, skiing, snowboarding
10.0 out of 10, Exceptional, (54)
"Beautiful fall foliage trip, Woodsy, cozy, private mountain getaway, close to everything house was well located, private, pleasant, well appointed and tastefully decorated, stunning views out the back. Beds and couches very comfortable!!! Hot tub works well. Good vibes overall. we were a party of 2 adults and 2 kids, couldve had 2 more people comfortably, but more than that would have been too much."
Private Mountain View minutes to Hiking, biking, golfing, skiing, snowboarding
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
2.0 star property
9.8 out of 10, Exceptional, (74)
"This is my third stay here. It's a wonderful cabin and property for nature lovers! The lovely deck is a perfect place to take in the surroundings. A pond, a waterfall, a fire pit and a cozy cabin, totally private, what more could you ask for? If you have physical limitations, just be aware that you have to walk up a small hill and some stairs from the parking area and the spiral staircase inside may be difficult to navigate for some. "
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (34)
"Great weekend! Beautiful location !!"
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (153)
"Our stay was wonderful, and the hosts were more than accomadating! Lovely home and very convenient to Ludlow and Okemo. "
Idyllic Lakefront House Suited Two Families
Spacious 3-story home near ski area with private hot tub, Ping-Pong
6.8 out of 10, (14)
"Enjoyed our stay. The home was cozy with lots of amenities. "
Spacious 3-story home near ski area with private hot tub, Ping-Pong
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
3.0 star property
9.0 out of 10, Wonderful, (39)
"Amazing house great price but note that there are only two split units cooling down the house which means one bed room only gets ac if the other bedrooms split unit is on and both doors are open"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (219)
"Very clean , everything we needed and more , beautiful hot tub , very cozy cabin nicely decorated "
Cozy Loft for two with Hot Tub
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.