Search Vacation Homes in Stockbridge

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Vacation Homes in Stockbridge

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (118)
"Great time and great place"
Beautifully renovated with fireplace and coffee bar

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, (24)
"Pleasant hosts. My daughter milked s goat! Great night’s sleep."
$171 nightly
The price is $192
Oct 20 - Oct 21
Total with taxes and fees
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (168)
"We really enjoyed our stay at the lake house. We had great views of the lake and the kitchen was very well stocked. The beds were comfortable and the house was very clean and nicely decorated. Thank you for the incredible stay and we will be staying again!"
Idyllic Lakefront House Suited Two Families

Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

10.0 out of 10, Exceptional, (6)
"Lovely rustic and cozy cabin stay"
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

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

10.0 out of 10, Exceptional, (110)
"Clean and great location!"
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Ski house 8 min from the mountain

9.6 out of 10, Exceptional, (20)
"House was cozy, had great facilities, the location was perfect and the owner was very responsive to any questions. Definitely would visit again. "
Ski house 8 min from the mountain

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

8.4 out of 10, Very Good, (28)
"The host and house manager are absolutely the best. Felt very taken care of - they went above and beyond."
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

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

9.8 out of 10, Exceptional, (26)
"Beautiful place."
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

9.8 out of 10, Exceptional, (219)
"Our family of 4 enjoyed our stay at this lakeside cottage. We paddled the lake in the canoe and kayaks and found the home to be a comfortable and relaxing retreat."
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

New Listing - Luxury log home with stunning views

10.0 out of 10, Exceptional, (31)
"We had a great time enjoying this beautiful home!! Great for family getaways!!"
New Listing - Luxury log home with stunning views

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

2.0 star property
9.8 out of 10, Exceptional, (77)
"The feel was so relaxing, felt like home.Im at a loss for words was just wonderful."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

9.8 out of 10, Exceptional, (37)
"Great property, cozy and well maintained!"
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

Perfect Woodstock Getaway! Lovely Riverside Home

9.8 out of 10, Exceptional, (8)
"We had a wonderful weekend at Charlie's house. The property was clean and welcoming and the fenced in backyard was excellent for our dog Riley"
Perfect Woodstock Getaway! Lovely Riverside Home

BRAND NEW: Beautifully Restored Timber Frame Barn w/ Hot Tub & Movie Theater

10.0 out of 10, Exceptional, (1)
"This place is amazing! Great location. Very smooth check in and check out . Good communication with owners. Very clean and new! "
BRAND NEW: Beautifully Restored Timber Frame Barn w/ Hot Tub & Movie Theater

Charming Ranch in the Woods - Woodstock Way

8.0 out of 10, Very Good, (2)
"This was the perfect place to celebrate our 20th wedding anniversary. Woodstock was a place we frequented throughout our dating years and our marriage. This home was close to town but private. It was absolutely beautiful inside and easy to get to. The owners were communicative from the moment we booked and responded promptly with any questions. It was so easy. We were able to go into town, and come back and relax at the house. It was absolutely perfect. It was as advertised as well. There...
Charming Ranch in the Woods - Woodstock Way

Snowberry Hill, 5 bedroom, Private Luxury Ski Home on Killington Mtn, sleeps 12

10.0 out of 10, Exceptional, (29)
"Wonderful weekend with friends. 10 minute drive to lifts and close to a few restaurants. Plenty of space at the house to spread out and relax"
Snowberry Hill, 5 bedroom, Private Luxury Ski Home on Killington Mtn, sleeps 12

Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts

10.0 out of 10, Exceptional, (84)
"It's a grand old house and the property is beautiful."
Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts

Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

10.0 out of 10, Exceptional, (66)
"The perfect place for our friends and family to stay!"
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

Rustic home with a private hot tub, fireplace, cable, & washer/dryer

9.6 out of 10, Exceptional, (57)
"Cute house nestled in the woods, great location and private hot tub on the deck! We enjoyed every second of it!"
Rustic home with a private hot tub, fireplace, cable, & washer/dryer

Country townhome - mountain view - walk to Village of Quechee - near Club & golf

9.0 out of 10, Wonderful, (36)
"Nice place overall and a very convenient location. Property was very clean and well equipped for a weekend stay of 4-5 people. The village of Quechee is very cute. Only thing to be aware of is the spiral stairs which could be tricky for people with limited mobility."
Country townhome - mountain view - walk to Village of Quechee - near Club & golf
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

Find out more about Stockbridge

Find out more about Stockbridge

Stockbridge Vacation Homes information

Number of reviews
1,015
Accommodation
785 Vacation Homes
Lowest Price
$192
Highest Price
$192

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