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Vacation Homes in Stockbridge

Quaint lakefront home with a fire pit and beautiful views

9.4 out of 10, Exceptional, (96)
"We had a great time staying at this cabin. It’s really well located and was perfect for our stay."
Quaint lakefront home with a fire pit and beautiful views

Pet-Friendly, Heart of Quechee | Jay Hill Home

2.0 star property
9.4 out of 10, Exceptional, (3)
"Perfect house for the weekend. Clean. Nice location. Everything was as described. "
Pet-Friendly, Heart of Quechee | Jay Hill Home

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

10.0 out of 10, Exceptional, (72)
"We absolutely LOVED our stay. The house and all its amenities were perfect for our ski trip, and we would be thrilled to come back again some time. "
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

Deere Run townhouse with private sauna - pool & tennis - walk to Lake Pinneo

9.0 out of 10, Wonderful, (24)
"We had a wonderful time in the condo. Clean, very accommodating - loved the fireplace!"
Deere Run townhouse with private sauna - pool & tennis - walk to Lake Pinneo

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (112)
"Very cozy, great kitchen. The beds are extremely comfortable. The surrounding area is beautiful with plenty to do. Highly recommend."
Beautifully renovated with fireplace and coffee bar

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

9.8 out of 10, Exceptional, (218)
"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

9.6 out of 10, Exceptional, (121)
"Another fun time at this well located, well appointed home."
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

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

10.0 out of 10, Exceptional, (58)
"Beautiful house right in the village. Easy access to both Sugarbush and Killington. Would definitely stay here again. "
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

Spacious country home, beautiful sunsets, 40 acres

9.8 out of 10, Exceptional, (36)
"Awsome place to stay for a week! "
Spacious country home, beautiful sunsets, 40 acres

The Brandon Inn - Fourth Floor Queen Room

8.4 out of 10, Very Good, (5)
"Clean, great location…restaurants, quaint interesting little shops… rent a vehicle and go hiking explore etc"
$170 nightly
The price is $188
Aug 10 - Aug 11
Total includes taxes and fees
The Brandon Inn - Fourth Floor Queen Room

Heated Saltwater Pool: Riverfront Home in Ludlow

10.0 out of 10, Exceptional, (12)
"We had a wonderful stay. The house was very clean and well maintained and very well stocked. The pool and surrounding area were beautiful. We enjoyed day hikes at buttermilk falls and echo lake, which are so close by. We highly recommend this place to anyone looking to spend a few relaxing days in Vermont."
Heated Saltwater Pool: Riverfront Home in Ludlow

Private! Sauna, 3BR/2Ba, Pet-Friendly | Twin Peaks

9.2 out of 10, Wonderful, (12)
"We really enjoyed our stay in Quechee. The location is convenient. The accommodations were great; plenty of towels, toiletries provided in the bathrooms, extra sheets and blankets. It’s great having a dog friendly place to stay. We’ll definitely book again the next time we visit family in VT. "
Private! Sauna, 3BR/2Ba, Pet-Friendly | Twin Peaks

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

9.6 out of 10, Exceptional, (25)
"Absolutely loved it!!! Amazing house. Will definitely stay again!"
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

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, (19)
"It is not luxurious, but is absolutely unique and fun! We loved it!"
$140 nightly
The price is $157
Aug 12 - Aug 13
Total includes taxes and fees
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Off Grid Glamping Shed with River Access

2.0 star property
$84 nightly
The price is $94
Aug 8 - Aug 9
Total includes taxes and fees
Off Grid Glamping Shed with River Access

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

2.0 star property
9.8 out of 10, Exceptional, (75)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

10.0 out of 10, Exceptional, (53)
"Cozy accommodations, great location, beautiful property, wonderful hosts."
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

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

9.0 out of 10, Wonderful, (34)
"Great location, cute condo, comfortable beds, modern kitchen."
Country townhome - mountain view - walk to Village of Quechee - near Club & golf

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

9.8 out of 10, Exceptional, (25)
"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, (213)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
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