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Compare 47 Cottages in Stockbridge with updated reviews, rates, and availability.

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

9.8 out of 10, Exceptional, (11)
"We loved the location and home! So close to Okemo, beautiful home right on the lake. The hottub and gas fireplace were appreciated after a day of skiing. We would definitely come back again!"
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Some places accept dogs. At The Paw House Inn, we CATER entirely to dog lovers

Some places accept dogs. At The Paw House Inn, we CATER entirely to dog lovers

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

10.0 out of 10, Exceptional, (52)
"It was such a lovely stay. Everything was super tidy, clean, comfortable and cozy. We especially loved reading about the story of the build. Would absolutely recommend! "
The price is AED 459
AED 720 total
includes taxes & fees
27 Mar - 28 Mar
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

9.4 out of 10, Exceptional, (16)
"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great location close to Killington. Accurate listing. Nothing fancy but all the necessities available. Was clean and comfortable. Driveway was plowed early for easy access in/out."
The price is AED 574
AED 1,835 total
includes taxes & fees
27 Mar - 28 Mar
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

Woodstock Village Carriage House

9.6 out of 10, Exceptional, (90)
"We loved the carriage house and its proximity to the town of Woodstock. Perfect to come home at the end of the day. Would definitely recommend to anyone visiting Woodstock! "
Woodstock Village Carriage House

Cozy Historic Hilltop Cottage with Mount Ascutney View

9.8 out of 10, Exceptional, (76)
"This was the perfect cottage for a winter getaway. I was solo, but the home could have easily accommodated many more. I loved the vintage touches and had a nice time listening to the classic vinyl records while enjoying a glass of wine and watching it snow. I had dinner outside on the patio one night and the view was lovely. It is just a few minutes drive from Woodstock and Quechee and I visited both several times. The cottage was clean and had everything I needed. Highly recommend for a quiet,...
Cozy Historic Hilltop Cottage with Mount Ascutney View

New Lakeside Cottage near Okemo and Killington

9.6 out of 10, Exceptional, (153)
"We had an amazing week swimming, hiking, paddling, and admiring gorgeous Lake Amherst. All of our favorite things were nearby - lovely hiking trails, and maple ice cream. Perfect location, well appointed kitchen, and perfect dock on the lake. Our family loved every moment and we hope to come back again."
New Lakeside Cottage near Okemo and Killington

Cozy Cabin Retreat

10.0 out of 10, Exceptional, (26)
"The property was perfect and quiet. The hosts were quick to respond and gave great directions and advice. Will definitely stay again."
Cozy Cabin Retreat

Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains

10.0 out of 10, Exceptional, (9)
"If you’re looking to spend a weekend with some friends at Killington this is definitely the most bang for your buck outside of the resort. 20 minute drive and plenty of plowed parking. "
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains

Pet-friendly Roxbury Farmhouse on 350 Acres!

3.0 star property
Pet-friendly Roxbury Farmhouse on 350 Acres!

Rustic Roxbury Ski Farmhouse With Trails!

3.0 star property
Rustic Roxbury Ski Farmhouse With Trails!

Cozy cottage on the river, minutes from skiing, horse events, and so much more!

10.0 out of 10, Exceptional, (7)
"We loved our stay at the Dark Horse Cottage. It was close to everything we wanted to do. We loved being near the little creek. They thought of everything for amenities. It was perfect for what we needed. "
Cozy cottage on the river, minutes from skiing, horse events, and so much more!

Killington Area Escape w/ Deck, Views & Hot Tub!

3.0 star property
Killington Area Escape w/ Deck, Views & Hot Tub!

Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

3.0 star property
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

Spruce Moose Cottage | Tiny House on 65 private acres

Spruce Moose Cottage | Tiny House on 65 private acres

Inviting A-frame Cabin w/ Saltwater Hot Tub!

3.0 star property
Inviting A-frame Cabin w/ Saltwater Hot Tub!

Lovely Brookfield Home w/ Private Deck & Views

3.0 star property
10.0 out of 10, Exceptional, (1)
" Lovely home, beautifully furnished "
Lovely Brookfield Home w/ Private Deck & Views

Lakefront Paradise Near Okemo & Killington

3.0 star property
Lakefront Paradise Near Okemo & Killington

Charming Updated Cottage

Charming Updated Cottage
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

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (485)
"This cabin couldn't be cozier! It really lives up to its name as a "romantic retreat". The window seat is perfect for a sunny afternoon nap or to curl up with a book and some cocoa by the warmth of the fire. Mornings are beautiful as the sun shines dappled light in the trees. So peaceful. The surround sound is also great, we connected our phone via bluetooth and the music enhanced the cozy ambiance. We enjoyed a walk on the little trail in the back, stargazing in the hot tub, and snuggling up to...
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

Mountain Green

2.0 star property
6.4 out of 10, (9)
"We had a great time-- the apartment was clean and cute and the linens fresh. "
The price is AED 717
AED 962 total
includes taxes & fees
8 Apr - 9 Apr
Mountain Green

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (234)
"We thoroughly enjoyed our 3 nights at Little Loft. We needed some R&R and that’s exactly what these few days were. We grilled, enjoyed the view with a snowy day/night, melted in the hot tub, and chilled by the fireplace at night. The cabin had everything we needed and then some. Communication was perfect. We couldn’t have asked for a better experience."
Cozy Loft for two with Hot Tub & Mtn Views
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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