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Vacation Homes in Stockbridge

Quaint lakefront home with a private deck, firepit, and dock

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 private deck, firepit, and dock

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

8.8 out of 10, Excellent, (23)
"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

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

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (110)
"Our stay was terrific! Such a lovely renovated home! "
Beautifully renovated with fireplace and coffee bar

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

Spacious country home, beautiful sunsets, 40 acres

10.0 out of 10, Exceptional, (34)
"Awsome place to stay for a week! "
Spacious country home, beautiful sunsets, 40 acres

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

9.8 out of 10, Exceptional, (217)
"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.

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

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"
The price is AED 533
AED 689 total
includes taxes & fees
20 Jul - 21 Jul
The Brandon Inn - Fourth Floor Queen Room

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

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

9.2 out of 10, Wonderful, (12)
"Great three night stay in a very quiet and secluded location. Minutes away from Woodstock and other points of interest. Long trail brewery is a short drive. Property was spacious and comfortable with a great sauna downstairs. Thank you! "
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

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

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, (16)
"It is not luxurious, but is absolutely unique and fun! We loved it!"
The price is AED 397
AED 527 total
includes taxes & fees
26 Jul - 27 Jul
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

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

9.2 out of 10, Wonderful, (32)
"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, (22)
"Beautiful place."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Off Grid Glamping Shed with River Access

2.0 star property
The price is AED 215
AED 344 total
includes taxes & fees
19 Jul - 20 Jul
Off Grid Glamping Shed with River Access

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

9.8 out of 10, Exceptional, (211)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Quechee - Four Season Resort Townhome

10.0 out of 10, Exceptional, (8)
"Very nice ski chalet with great kitchen, large and private bedrooms and a hot tub. Very suitable for a small family retreat."
Quechee - Four Season Resort Townhome
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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