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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 719 Vacation Homes in Stockbridge with updated reviews, rates, and availability.

Beautifully renovated with fireplace and coffee bar
Smart TV, fireplace, books

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (102)
"The community, this unit in particular, and its hosts are all spectacular beyond belief. There was one technical/communication glitch that can easily be remedied. Prior communications were encrypted in VRBO platform. When I arrived, I needed to access those in order to refresh my recollection on entry instructions. There's no cellular internet service in the area (need wi-fi connection). Unable to enter the unit, I likewise could not connect to the host-provided wi-fi. I had some of the...
Beautifully renovated with fireplace and coffee bar
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Aerial view

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, (6)
"We had a wonderful time staying with Miken and Dave! The barn is a super cozy spot, the kitchenette has everything you need, and the goats (plus some piglets) were an un-baaa-levable highlight! This farm is beautiful and everything we were hoping for. Thank you for an incredible stay 3"
The price is AED 441
AED 576 total
includes taxes & fees
2 May - 3 May
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Property grounds

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

9.8 out of 10, Exceptional, (22)
"House is 1 minute or less from the Skye Peak Gondola, which as convenient for skiing. Clean house, has lots of room and games for families. Hot tub was really nice too."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee
TV, fireplace, books, music library

Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee

9.4 out of 10, Exceptional, (42)
"Lovely, clean property in beautiful setting. Cozy little escape! So close to amazing trails and hikes. Gorgeous setting. We have family in QueChee and it was perfectly located and so nice to have our own space! Would love to stay there again!"
Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont
Miscellaneous

Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont

10.0 out of 10, Exceptional, (2)
"The property was perfect for a Vermont getaway that will allow you to enjoy the autumn views and still give you the opportunity to engage in plenty of activities if you desire. Highly recommend this home!!"
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont
Spacious country home, beautiful sunsets, 40 acres
Exterior

Spacious country home, beautiful sunsets, 40 acres

10.0 out of 10, Exceptional, (32)
"House was exactly as described in listing."
The price is AED 496
AED 1,785 total
includes taxes & fees
29 Apr - 30 Apr
Spacious country home, beautiful sunsets, 40 acres
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Property grounds

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

9.8 out of 10, Exceptional, (205)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
Property map

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

9.2 out of 10, Wonderful, (36)
"Fantastic location for easy ski on ski off."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo
Fridge, microwave, oven, stovetop

Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

10.0 out of 10, Exceptional, (51)
"Fantastic Vermont farm house in a great setting close to Okemo and Killington. Very accommodating, clean, warm and comfortable. After skiing we enjoyed just sitting around the fireplace and talking. We plan on returning next year."
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
TV, fireplace

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

10.0 out of 10, Exceptional, (3)
"Lovely rustic and cozy cabin stay"
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA
Exterior

The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA

The price is AED 1,010
AED 2,229 total
includes taxes & fees
27 Apr - 28 Apr
The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (25)
"If you're looking for the perfect getaway near Killington, look no further than this incredible rental home! From the moment we stepped inside, we were blown away by how spacious and welcoming the property felt. It easily accommodated our large group, with plenty of room for everyone to relax and enjoy themselves.The home has such a cozy, homey atmosphere that made it hard to leave! We spent our evenings gathered around the real fireplace, which added so much warmth and charm to the experience....
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn
Fridge, microwave, oven, stovetop

Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn

10.0 out of 10, Exceptional, (1)
"Was an amazing location with tons to do. Clean property and cozy!"
Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn
Off Grid Glamping Shed with River Access
Property grounds

Off Grid Glamping Shed with River Access

2.0 star property
The price is AED 239
AED 370 total
includes taxes & fees
27 Apr - 28 Apr
Off Grid Glamping Shed with River Access
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola
Outdoor dining

Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

9.6 out of 10, Exceptional, (20)
"Great place for our guys weekend. Place was clean and beds were comfortable. Would definitely rent again."
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (32)
"Clean house with food amenities and great location."
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Outdoor dining

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

8.6 out of 10, Excellent, (25)
"Cool location, perfect basic ski house"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

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

9.6 out of 10, Exceptional, (119)
"The house was great for our large gathering of multiple families with kids. The commercial range with griddle was awesome and made cooking for the group so much easier. The house had multiple living spaces so it allowed a few in the group that had to work during the week to find a nice space away from the main group. Proximity to Killington was great!We were there during the Presidents Day holiday week so our check in got delayed (5pm) and check out was a bit early (10am), but totally...
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking
Quaint lakefront home with a private deck, firepit, and dock
Property grounds

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

9.4 out of 10, Exceptional, (93)
"We rented this property to be close to skiing at Okemo. Here are things we wanted to share:Location: it's a 5 minute drive to Okemo - fantastic! The cottage is at the base of Lake Pauline, directly across from a busy road. The road noise was noticeable, and it was winter with windows closed. It was not a secluded cabin in the woods.Check in: the code did not work. When we contacted Vacasa, we were told that they could reset the door code remotely. The back door was not locked, so we got in...
Quaint lakefront home with a private deck, firepit, and dock
Spectacular 4 Bed Killington Home
Exterior

Spectacular 4 Bed Killington Home

9.8 out of 10, Exceptional, (118)
"This is our second year in a row renting this house. Plenty of room for 2 families of four and the location to Killington ski are is perfect. The wood stove is great for drying out ski gear and plenty of room for cooking and eating for 8. Communication with Wally was clear and responsive. Another great ski getaway!"
Spectacular 4 Bed Killington 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 in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

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
Cozy Loft for two with Hot Tub & Mtn Views
Exterior

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (236)
"My wife and I stayed in "The Little Loft" for a ski trip to Sugarbush. The cabin it small for sure but offers everything you will need from a standpoint of short term livability. We used that hot tub daily / nightly after skiing all day, had a great meal we grilled out and had a few nice bonfires as well. If you do not want to have to drive 30 minutes for dinner or shop for your food and cook it, then you may find it a small inconvenience but for us we intentionally wanted to be in a quiet cabin...
Cozy Loft for two with Hot Tub & Mtn Views
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
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.