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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 49 Cottages in Stockbridge with updated reviews, rates, and availability.

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

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
1 bedroom, free WiFi, bed sheets

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
Fridge, microwave, oven, stovetop

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 SAR 469
SAR 736 total
includes taxes & fees
27 Apr - 28 Apr
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Fridge, microwave, oven, stovetop

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.
Smart TV

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice time, great location"
The price is SAR 553
SAR 1,672 total
includes taxes & fees
16 Apr - 17 Apr
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Woodstock Village Carriage House
Exterior

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
Exterior

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
Cozy Cabin Retreat
1 bedroom, iron/ironing board, travel crib, free WiFi

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
Exterior

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!
House (4 Bedrooms) | Interior

Pet-friendly Roxbury Farmhouse on 350 Acres!

3.0 star property
Pet-friendly Roxbury Farmhouse on 350 Acres!
Rustic Roxbury Ski Farmhouse With Trails!
Interior

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!
Fridge, microwave, oven, stovetop

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!
Interior

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!
Microwave, oven, stovetop, dishwasher

Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

3.0 star property
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Inviting A-frame Cabin w/ Saltwater Hot Tub!
House (2 Bedrooms) | Interior

Inviting A-frame Cabin w/ Saltwater Hot Tub!

3.0 star property
Inviting A-frame Cabin w/ Saltwater Hot Tub!
Spruce Moose Cottage | Tiny House on 65 private acres
Fridge, oven, stovetop, cookware/dishes/utensils

Spruce Moose Cottage | Tiny House on 65 private acres

Spruce Moose Cottage | Tiny House on 65 private acres
Lovely Brookfield Home w/ Private Deck & Views
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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
Interior

Lakefront Paradise Near Okemo & Killington

3.0 star property
Lakefront Paradise Near Okemo & Killington
Charming Updated Cottage
Fridge, microwave, oven, stovetop

Charming Updated Cottage

Charming Updated Cottage
Ski, Hike & Fish: Modern Rutland Home
Interior

Ski, Hike & Fish: Modern Rutland Home

3.0 star property
Ski, Hike & Fish: Modern Rutland Home
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/MTB Home with Mountain Views near Killington/Woodstock/Green Mountain Trails
Terrace/patio

Ski/MTB Home with Mountain Views near Killington/Woodstock/Green Mountain Trails

10.0 out of 10, Exceptional, (1)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
The price is SAR 563
SAR 1,912 total
includes taxes & fees
16 Apr - 17 Apr
Ski/MTB Home with Mountain Views near Killington/Woodstock/Green Mountain Trails
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
TV, fireplace, DVD player, books

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

10.0 out of 10, Exceptional, (489)
"The cabin had everything we needed, was comfortable, and quiet. It was clean and the beds were comfortable. We had a nice getaway to celebrate a milestone birthday. Jeff couldn't have been nicer and provided ample information about the area and where to eat, etc. Would highly recommend staying at the cabin if you're looking for a quiet escape from your regular life...even if you already live in rural new england as we do. "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
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, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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.