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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 580 Vacation Homes in Stockbridge with updated reviews, rates, and availability.

Beautifully renovated with fireplace and coffee bar
Enter the home to an open living space

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (94)
"Nice place. we had a great time. "
Beautifully renovated with fireplace and coffee bar
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Lake

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

9.8 out of 10, Exceptional, (202)
"Great place after a long day of skiing. Very close to Jackson Gore base area. The house was clean and communication was spot on. "
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

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

9.8 out of 10, Exceptional, (19)
"The gondola house was perfect for our group. It was spacious and comfortable. Loved having a bathroom on every floor. It was well stocked with everything we could’ve needed. I don’t have one bad thing to say about it. The hot tub was just lovely after a long day of skiing. Would not hesitate to rent this again and highly recommend it."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Property grounds

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, (2)
"The hosts were super communicative and accommodating to everything we needed, even going so far as to give us a tour of the property when we arrived late at night. The space is super cozy (we stayed during a snow showers and very cold weather) and we loved being able to relax in the super modern and clean living space while being able to feed all the wonderful goats just outside. Being introduced to each goat on a first name basis and being told about their personality was so funny,. We will...
The price is SAR 450
SAR 588 total
includes taxes & fees
4 Mar - 5 Mar
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

8.0 out of 10, Very Good, (2)
" short stay "
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Modern Farm House…minutes to Okemo; 2 King beds!
Interior

Modern Farm House…minutes to Okemo; 2 King beds!

9.4 out of 10, Exceptional, (9)
"We were a few families visiting for a ski weekend. Location was great and the house was clean, updated, and had plenty of space. Only thing we thought was inconvenient was the lack of spare TP! "
Modern Farm House…minutes to Okemo; 2 King beds!
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Living area flooded with natural light.

BruinsDen - Ski On Ski Off (Home Stretch Trail)

10.0 out of 10, Exceptional, (11)
"Wonderful home! Excellent layout for family bonding. Hot tub was great. Skiing equipment storage area was Lu fantastic. Easy ski-in ski-out!!! Communication with host was excellent!! Beds were comfy! Would highly recommend! "
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

9.6 out of 10, Exceptional, (36)
"The home is as described with plenty of space for my family of 5. The kitchen was well stocked, and the bathrooms were clean. Plenty of towels and the beds were firm with clean sheets. The views of Lake Rescue were beautiful. The driveway was snow-covered, but with a 4WD, you should have no issue. The 'commute' to Okemo was easy - 8min max. The house seems to have been empty, so a musty smell permeated the home for the first day until the air circulated a few times. Not a big deal. The gas...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

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

9.8 out of 10, Exceptional, (49)
"This is a lovely home -- spacious, beautifully furnished, and well-located, about 15 minutes from Okemo & downtown Ludlow. 4wd recommended for winter visitors: the house is up a steep hill, and in January the road surface was packed-down snow, so it was slippery for cars without all-wheel-drive."
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

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
Killington, Vermont Ski House w/ Hot Tub and Sauna
I Our snow country home welcomes you!

Killington, Vermont Ski House w/ Hot Tub and Sauna

9.4 out of 10, Exceptional, (84)
"The perfect home to come back to after a day of skiing with a sauna and hot tub to lounge in. So spacious and close to the mountain!"
Killington, Vermont Ski House w/ Hot Tub and Sauna
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill
Mountain Views from the minute you drive in to the house

6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill

10.0 out of 10, Exceptional, (23)
"Had a wonderful stay! Was cozy, clean, with a well stocked kitchen. Highly recommend. Evan was a lovely host. "
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill
Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn

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

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

8.6 out of 10, Excellent, (22)
"Basic ski house, in cool spot. 10 mins from bear mtn. Would definitely stay here again. "
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!
Welcome to your Ideal Killington Escape!

Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!

10.0 out of 10, Exceptional, (16)
"Close to the mountain. Close to restaurants. Perfect house for what we were looking for "
Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!
Stunning 4 bed Timber Frame Ski Retreat on 6 acres
Aerial view

Stunning 4 bed Timber Frame Ski Retreat on 6 acres

10.0 out of 10, Exceptional, (2)
"Great property for a ski trip up to the mountains!"
Stunning 4 bed Timber Frame Ski Retreat on 6 acres
Idyllic Lakefront House Suited Two Families
View from deck

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (157)
"We really enjoyed our stay at the lake house. We had great views of the lake and the kitchen was very well stocked. The beds were comfortable and the house was very clean and nicely decorated. Thank you for the incredible stay and we will be staying again!"
Idyllic Lakefront House Suited Two Families
New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b
Exterior

New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b

10.0 out of 10, Exceptional, (44)
"We had a spectacular stay! Ed was great. He was super helpful and a great host. His house was exactly what we needed. The pictures truly don’t do it justice. Plenty of room, high end finishes, charming decorations and breathtaking views of the mountain. Highly recommend this home!!!"
New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b
Perfect Ski in Ski Out House with Fireplace & Hot Tub!!
Ski on ski off on Great Eastern Trail!!!

Perfect Ski in Ski Out House with Fireplace & Hot Tub!!

10.0 out of 10, Exceptional, (80)
"Our party enjoyed a great stay with epic snow!"
Perfect Ski in Ski Out House with Fireplace & Hot Tub!!
Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views
Exterior

Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views

9.2 out of 10, Wonderful, (19)
"I loved the size and layout of this house. So many rooms and beds with lots of open communal space so we could all sleep comfortably but also all hang out in one room when we wanted to. The drive to Killington to ski everyday was so quick and easy and lots of food options around in both directions!"
Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning 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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Other property types in Stockbridge

Cozy Loft for two with Hot Tub & Mtn Views
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (230)
"Great stay in the mountains. Listing is exactly as advertised. Jeff was great "
Cozy Loft for two with Hot Tub & Mtn Views
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, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

8.4 out of 10, Very Good, (27)
"It’s a great location, and the unit is well updated, but being able to lock it while you’re away skiing the whole day is pretty important. When I reached out to the property manager about this, and also a disgusting towel left near the toilet on arrival, the response was basically oh no! That’s awful! We’ve told someone.. aaaand nothing ever happened about either thing. These issues weren’t insurmountable, but doing nothing at all about them just left a terrible impression."
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
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.