Search Vacation Homes in Stockbridge

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7 Feb - 9 Feb
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28 Feb - 2 Mar
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28 Mar - 30 Mar

Compare 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, (92)
"We had a great winter weekend! The accommodations were just what we needed, perfect location and the coffee bar was amazing! We cant wait to come back again!"
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, (201)
"Beautiful cozy cottage, but the road is a little loud. The creek and backyard are gorgeous."
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)
"Great Location! Very short drive to Skyeship Gondola. Property was well equipped for all our needs."
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 AED 441
AED 576 total
includes taxes & fees
2 Feb - 3 Feb
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Cozy Vermont House Near Killington and Woodstock. Discounted lift tickets!

Cozy Vermont House Near Killington and Woodstock. Discounted lift tickets!

8.0 out of 10, Very Good, (1)
" short stay "
Cozy Vermont House Near Killington and Woodstock. Discounted lift tickets!
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)
"It is the perfect house for two families to stay in for a ski weekend. There are plenty of arcade and board games to entertain the teens. We will be back!"
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! "
The price is AED 3,161
AED 6,307 total
includes taxes & fees
2 Feb - 3 Feb
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, (48)
"We went up in December to Ski Okemo. This is a great house and has all amenities including an awesome fireplace and large eating area. Great location for two of three families to go away together and enjoy VT!"
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, (22)
"Our family stayed at Evan's home because we were attending a wedding (conveniently up the road) at Mountain Top Resort. The home gushes with Vermont charm! It was beautifully and thoughtfully decorated which made our stay so cozy. Evan thought of everything- from exact GPS directions, to helpful notes around the home to help his guests be comfortable! Evan was very helpful at every stage of our stay! We would absolutely 100% recommend staying at Evan's beautiful home!"
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

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

8.8 out of 10, Excellent, (21)
"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)
"We had two families stay at the home the first week of April during Spring Break so we could do a couple of days of skiing. The house was wonderful. It had so many beds, which made it great for the 6 kids and then separate bedrooms for the two couples, which was great. We enjoyed making a fire in the fireplace at the end of the day as we played board games with the family..we especially enjoyed playing LCR (Left Center Right). Kristin's communication was incredible. She was always so quick to...
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, (155)
"Enjoyed our stay. 5 minute drive to Jackson gore base made it nice to go back and forth with kids. Ursula was very attentive and did her best to make sure everything was in good order. "
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, (43)
"We had such a wonderful stay! The home owner was happy to greet us and show us the rooms and how to use the fireplace and hot tub. The home is warm, cozy and inviting. It was the perfect stay for our group of ladies looking to enjoy the slopes together! "
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, (79)
"Great cabin for a family ski trip. Right on the trail with easy access. Property is clean, well stocked and maintained. Would definitely come back and stay here."
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

9.0 out of 10, Wonderful, (18)
"A bunch of friends and I wanted to do a long weekend of mountain activities and this place fit our needs perfectly. Irina was helpful with the check-in check-out process and followed up with a text in addition to the email. Would certainly go back!"
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
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (227)
"Such a cute, quaint space. Would love to come back in the summer to take full advantage of the area. Came in the winter time so we could not use the deck and fire pit. Definitely a great feature for extra space to eat on the deck during warmer time. Pull up coffee table inside is convenient for eating during Winter, since there is no other dining area. Winter time is great if you ski/snowboard, close to ski areas. We went into Rochester for lunch one day, and was a nice small "downtown". The...
Cozy Loft for two with Hot Tub
Spectacular opportunity to enjoy the finest property in Killington Summit
Outside view in the wintertime.

Spectacular opportunity to enjoy the finest property in Killington Summit

9.4 out of 10, Exceptional, (22)
"This place was great, Communication with the Killington Rental Associates was wonderful. The house was as it photographs. It was a perfect spot to ring in the New Year. After skiing, the hot tub and Sauna were a welcome retreat for the weary skiing crowd, the Kitchen was well stocked with just about anything you could need to prepare meals for a large crowd. The Bar was an added highlight for apre-Ski. There was enough space for a large crowd to gather in one spot, and enough spots to...
Spectacular opportunity to enjoy the finest property in Killington Summit
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
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.