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Check prices for these dates

Next weekend
24 Muh. - 26 Muh.
In two weeks
31 Muh. - 2 Saf.
In one month
14 Saf. - 16 Saf.
In two months
14 Rab. I - 16 Rab. I

Compare 547 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, (90)
"Our stay was nice and cozy! The condo held our family nicely and it had everything we needed— we especially loved the coffee bar. It was an easy drive into town and very picturesque. "
Beautifully renovated with fireplace and coffee bar
Valley View Retreat is a tastefully decorated home.
Living area

Valley View Retreat is a tastefully decorated home.

10.0 out of 10, Exceptional, (1)
"It was a great ski house, minutes from the slopes. We weren’t looking for anything other than a clean and comfortable place from which to go skiing, and this house fit the bill. It was clean, roomy, functional, beautiful setting and a hot tub to cap the ski day. No complaints. "
Valley View Retreat is a tastefully decorated home.
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, (200)
"My family and I just returned from our New Years stay at “Cozy Cottage”. The home is beautifully appointed and equipped with everything you could possibly need. Waking up every morning in the sun room overlooking the lake was an absolute dream especially on a snowy day. The location is fantastic, as it’s a stones throw to Okemo, and about a 7 min drive to the town of Ludlow where you will find a grocery store, quaint shops, and dining. We definitely plan to return!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Walk to Pickle Barrel & Jax. Hot tub & Views

Walk to Pickle Barrel & Jax. Hot tub & Views

2.0 star property
10.0 out of 10, Exceptional, (2)
"This is the 2nd time we’ve stayed in this beautiful home and it was just as we remembered. Comfortable bedrooms, deck/yard/hot tub amazing, proximity to so many restaurants as well as the mountain. Everything was clearly communicated throughout our stay and the hosts were incredibly responsive and available for anything we could need. Would highly recommend!"
Walk to Pickle Barrel & Jax. Hot tub & Views
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 SAR 1,969
SAR 3,886 total
includes taxes & fees
27 Jan - 28 Jan
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Cozy Vermont House Near Killington and Woodstock. Discounted lift tickets!

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

Cozy Vermont House Near Killington and Woodstock. Discounted lift tickets!
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, (35)
"Convenient to Okemo. Has everything you need for a ski week or weekend! "
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
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, (18)
"Gorgeous property with everything that we needed! It was relaxing and comfortable for everyone. The kids had a blast! The property management team was great with communication and offered early check in and late check out. Would absolutely stay here again!"
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
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, (20)
"Very peaceful & relaxing. "
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
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, (82)
"Perfect house. This is our second time there and we had a wonderful experience."
Killington, Vermont Ski House w/ Hot Tub and Sauna
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Interior

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

10.0 out of 10, Exceptional, (65)
"This home was absolutely beautiful. Great location as well. We had a group of 11 friends and family who have skied together, some for over 40 years. Even a 7 year old. It was perfect! Everyone had their own space, we could all dine together, hang out together, or not. It was perfect. We highly recommend "
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
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!
Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests
Upstairs living area for all of your family and friends to sit back and relax. Lots great views to enhance your stay

Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests

9.2 out of 10, Wonderful, (29)
"Beautiful property! The lovely home is clean and convenient to skiing/ restaurants/ shopping.Very quiet neighborhood and so relaxing. The hot tub was well maintained and easily assessable.The property actually has 6 rather than 5 bedrooms. Most bathrooms are very small. I would definitely consider renting it again."
Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests
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
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, (1)
"We had a great stay. Cozy post and beam with quick access to Okemo."
Stunning 4 bed Timber Frame Ski Retreat on 6 acres
Lovely wooded home with deck, enclosed porch - dog-friendly

Lovely wooded home with deck, enclosed porch - dog-friendly

7.8 out of 10, Good, (21)
"Our family had plenty of room. There was no instructions regarding the trash and recyclables. There were no grab bars in the stone shower. There should have been a chair in the bedroom. There should be a sensor light outside when you come home in the dark. Per the notice we could have parked 4 cars, no way with that steep driveway. Parking is a little tricky. With that said everything was fine. Our stay was great. We really were only there to sleep."
Lovely wooded home with deck, enclosed porch - dog-friendly
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, (17)
"My friends and I enjoyed the house immensely. My husband loved the sauna, while my friends enjoyed the hot tub. The kitchen was well equipped and had everything we needed to prepare meals for 16 people. Lots of space for a large group. Small issue with the deck furniture but was resolved immediately. Very impressed with Irina and her responsiveness to queries. Recommend very highly."
Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views
Ski-in/out sunrise condo with pool & hot tub - great ski retreat

Ski-in/out sunrise condo with pool & hot tub - great ski retreat

8.8 out of 10, Excellent, (79)
"Property was nice and location was great even for an of season stay. Lots of fun close by like the killington adventure center & visiting small toes like Woodstock & ludlow. Also hiking close by!! We were a bit disappointed that the indoor pool & hot tub were closed until the peak winter season so may mention that in the listing. We loved having the fire place & sauna inside unit. "
Ski-in/out sunrise condo with pool & hot tub - great ski retreat
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
The Brandon Inn - Fourth Floor Queen Room
Point of interest

The Brandon Inn - Fourth Floor Queen Room

8.4 out of 10, Very Good, (5)
"Clean, great location…restaurants, quaint interesting little shops… rent a vehicle and go hiking explore etc"
The price is SAR 544
SAR 694 total
includes taxes & fees
20 Jan - 21 Jan
The Brandon Inn - Fourth Floor Queen Room
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, (226)
"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
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
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
"The cabin was peaceful and everything was provided, plus some!" Stacy S

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

10.0 out of 10, Exceptional, (477)
"It was great! Nice spot, great hottub and close to ski slopes"
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.