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Compare 565 Vacation Homes in Stockbridge with updated reviews, rates, and availability.

Spacious country home, beautiful sunsets, 40 acres
Brand new chef's kitchen

Spacious country home, beautiful sunsets, 40 acres

9.8 out of 10, Exceptional, (25)
"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
Living area

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
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
Spectacular 4 Bed Killington Home
Exterior

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!
Enjoy the views of Bear Mountain directly from the hot tub!

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 AED 774
AED 2,616 total
includes taxes & fees
25 Nov - 26 Nov
Slopeside Chalet - Ski to and from your 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!
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
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, (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
The Gallery at Six, circa 1880

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
Enter the home to an open living space

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (83)
"Totally loved it, recommend. "
Beautifully renovated with fireplace and coffee bar
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, (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

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
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 AED 569
AED 728 total
includes taxes & fees
25 Nov - 26 Nov
The Brandon Inn - King Room
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Interior

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

New! 4BR/3.5 BR luxurious escape to Quechee with large private yard

10.0 out of 10, Exceptional, (1)
"A mix of business and pleasure. The house was an ideal base camp for our informal discussions and getting to know each other better. We had a couple meals there - well equipped kitchen and functional grill made it easy. A relaxing productive stay 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
beautiful fall day at house view from deck

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

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

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
View from deck

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

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
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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
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, (220)
"The Cozy Loft was the perfect place to get away from everyday work and left stressors. It provided us a place to rest and relax. It was also not far from towns to explore (great hiking, restaurants, antique shopping). Would highly recommend to others traveling to that area. "
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.