
Vacation rentals in Stockbridge
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Top-rated vacation rentals in Stockbridge
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Popular amenities for Stockbridge vacation rentals
Other great vacation rentals in Stockbridge

Breathtaking Lakeside Retreat!
Second year renting. Great place, definitely would recommend. Hope to return next year. Brooke is a fantastic host. Thank you

THE CABIN....a Vermont log home
Bill's cabin was excellent. Rustic and rural but close to Killington and Pico, and a quick ride to Rutland. It was clean, comfy and had all we needed for a great little stay. It got a thumbs up from my wife and that is a high standard to meet. She even liked the king bed so much she was looking for the label to get one like it for home. I'm a guy and don't need much. The cabin made me feel like I was staying at a friend's house. You can nit-pick about the lighting and other minor stuff, but to me this place was a 10 out of 10 stars. We may be back next year for a longer ski vacation. Thanks Bill.

Still 89 Trails Open, Low, Low Rates
Convenient to the slopes via the shuttle that picks up out front. Able to walk to a good restaurant, Still on the Mountain. Place is comfortable and has everything we needed for a weekend skiing.

Killington Racquetball House
This was our second time staying at the racquetball house and it was just as incredible as the first. Lucked out with some great spring skiing on Friday, and checked into the Airbnb after. The house is very conveniently located to the mountain. We made full use of the court. Played racquetball, volleyball, dodgeball, kickball, pickleball, wall ball. Basically just spent all weekend playing games in the court and then relaxing in the hot tub to end the day. The living room / kitchen area is a great gathering layout. We will definitely be back.

Modern Retreat next to Mountain Top Inn,Killington
I couldn't recommend this place more! My cousins and I had a great time and Uli is super attentive. The hot tub has a great view of the lake, it was also salt water which I love. The space was extremely cozy and exactly what we needed. We snowboarded pico and killington and it was about a 25-30 minute ride. We will for sure be back! Thank you guys so much!

Luxury Modern Cabin near Okemo & Killington
Stephanie was an Incredible host! The listing matched her description and the property looked even better upon checking in. Stephanie maintains this property really well and I couldn’t have felt any more at home. The home was clean and had a perfect cozy feeling to it. In addition, this was really close to the mountain, which made the getaway even better. I enjoyed the privacy and waking up to a nice snow dusting before my trip to the mountain. I highly suggested staying at Stephanie’s property if you’re looking for a quick getaway. I certainly will be looking to book again soon. Thank you Stephanie!

Private Home with Hot Tub 1 mile from Sugarbush
We had an amazing stay at Don’s place. The location was perfect, allowing us to enjoy four great days of skiing. Don was a fantastic host, making everything easy from start to finish. The house was ideal for our extended family of eight, offering plenty of space and comfort. If you’re looking for a spacious, well-located home near Sugarbush, I highly recommend staying here!

Crescent Lake home swim, golf and hike
We loved the home. Perfect for our ski vacation to Sunapee and Okemo! It was one of our favorite Airbnb’s. So cozy, great location, great atmosphere, great decorating, etc. We just felt right at home from a minute. We walked in the door Beds comfortable. The upstairs is great if you have a few kids who just want to crash on a bunch of different beds. Laurie, who we mostly communicated with, was fantastic. So nice and so easy to get in touch with if we needed her for anything. Thanks for a great day! Hope to come back someday.
Quick stats about vacation rentals in Stockbridge
Total rentals
70 properties
Nightly prices starting at
ﺩ.ﺇ110 before taxes and fees
Total number of reviews
2.9K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Frequently Asked Questions
Are there family-friendly vacation rentals in Stockbridge?
Stockbridge has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Stockbridge have wifi?
Absolutely! We offer over 30 house rentals with wifi in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Stockbridge?
Four-legged friends are welcome in Stockbridge. Choose from more than 40 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Stockbridge?
Experience the best of Stockbridge with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Stockbridge?
Yes! Work meets play with ease at over 20 vacation rentals in Stockbridge featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Stockbridge have free parking?
Absolutely! We offer over 30 house rentals with free parking in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Stockbridge have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Stockbridge?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 30 homes with a kitchen, over 30 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
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- Cochran's Ski Area
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