Search Vacation Homes in Stockbridge

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 547 Vacation Homes in Stockbridge with updated reviews, rates, and availability.

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

Walk to Pickle Barrel & Jax. Hot tub & Views

2.0 star property
10.0 out of 10, Exceptional, (1)
"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!"
The price is AED 1,561
AED 2,460 total
includes taxes & fees
14 Jan - 15 January 2025
Walk to Pickle Barrel & Jax. Hot tub & Views

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

8.8 out of 10, Excellent, (19)
"Very peaceful & relaxing. "
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

9.2 out of 10, Wonderful, (66)
"Best place to visit for fall leaf peeping! Very enjoyable experience "
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

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!

BruinsDen - Ski On Ski Off (Home Stretch Trail)

9.8 out of 10, Exceptional, (10)
"Amazing. So clean. Room for everyone to spread out and enjoy their time."
The price is AED 1,995
AED 3,891 total
includes taxes & fees
6 Jan - 7 January 2025
BruinsDen - Ski On Ski Off (Home Stretch Trail)

Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Had a nice stay with friends at this beautiful house. Very spacious with plenty of beds and bathrooms. Spacious and very clean in quiet, peaceful location. Hosts quickly responded to any questions."
Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!

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

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

9.2 out of 10, Wonderful, (28)
"Everything about this weekend was perfect! Thank you for letting us stay in your beautiful home! "
Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests

Killington Getaway In Private Community

8.8 out of 10, Excellent, (19)
"Perfect for a ski trip. "
Killington Getaway In Private Community

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

10.0 out of 10, Exceptional, (94)
"We had great stayed, be back next year "
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

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

9.8 out of 10, Exceptional, (23)
"Great getaway with family. The home was very clean and well stocked with towels,linens, blankets, and most essentials. The first snowfall of the season made the Mountain Views picture perfect. Very close to Woodstock and Killington. "
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen

Valley View Retreat is a tastefully decorated home.

Valley View Retreat is a tastefully decorated home.

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

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

9.4 out of 10, Exceptional, (92)
"We wanted to visit VT and decided to rent this beautiful little home on quiet Lake Pauline in Ludlow. We were not disappointed in any way. Serene location, clean, cozy, and welcoming home, excellent nearby restaurants and other attractions.A great 50th anniversary getaway!"
Quaint lakefront home with a private deck, firepit, and dock

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

9.8 out of 10, Exceptional, (199)
"We had a wonderful 4 days/nights at Cozy Cottage. Perfectly named, well appointed decor and comfortable beds. Perfect for families. The fire pit, kayaks and conoe along with the string lights and sitting areas to watch the wood ducks and beaver family was the perfect way to decompress from the rat race."
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (88)
"Amazing, thank you!"
Beautifully renovated with fireplace and coffee bar

4 Season Secluded Lakefront Home near Ski Mountains

9.4 out of 10, Exceptional, (67)
"Beautiful spot..definitely a camp, very rustic. We enjoyed a canoe trip around the pond."
4 Season Secluded Lakefront Home near Ski Mountains

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

9.8 out of 10, Exceptional, (52)
"This is our second stay at Joel’s condo. His improvements to the lower floor are very nice and made a lot of sense. We enjoyed the location and condo once again. Joel continues to be very thoughtful and helpful. A great place to get away, relax, and have fun. We also got some late season skiing in for those of us who enjoy the slopes."
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

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

9.6 out of 10, Exceptional, (60)
"Very comfortable stay. Convenient to Killington, Woodward reservoir, and Woodstock not far away. Great communication. "
☆ SKI ON & OFF ☆ Spruce Glen C on Great Eastern Trail w/AC, Sauna, Fireplace
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.
Don't see what you're looking for?
See all available properties in Stockbridge
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Stockbridge

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"Like property— sad the lift that made it ski and in out was closed due weather conditions "
The price is AED 1,488
AED 2,121 total
includes taxes & fees
26 Dec - 27 Dec
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (222)
"We had the best time at Jeff’s perfect cozy ‘little loft’! It exceeded expectations! We especially enjoyed the hot tub after long days of skiing!"
Cozy Loft for two with Hot Tub

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (134)
"Cabin had everything we needed and more. We found it to be a great location for the small day trips we did to surrounding towns. Location is just gorgeous. "
The price is AED 882
AED 1,715 total
includes taxes & fees
6 Jan - 7 January 2025
Stetson Hollow Cabin by Stetson Brook
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.