Vacation rentals in Stockbridge

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Popular amenities for Stockbridge vacation rentals

Stay near Stockbridge's top sights

Thundering Brook Falls Trail49 locals recommend
Green Mountain National Golf Course35 locals recommend
Clear River Tavern23 locals recommend
Gifford Woods State Park20 locals recommend
Original General Store20 locals recommend
Tozier's Restaurant17 locals recommend

Other great vacation rentals in Stockbridge

Guest favorite
A stone pathway leads to a lakeside retreat, flanked by lush greenery and blooming hydrangeas. The tranquil waters of Lake St. Catherine are visible in the background, bordered by rolling hills under a clear blue sky.
Home in Wells
5 out of 5 average rating, 12 reviews

Breathtaking Lakeside Retreat!

BrianRating, 5 stars2 months ago
Second year renting. Great place, definitely would recommend. Hope to return next year. Brooke is a fantastic host. Thank you
Guest favorite
An inviting living area is highlighted by a stone fireplace, surrounded by wooden walls and a peaked ceiling. A cozy seating arrangement includes a leather couch and two footrests, while a small table holds a lamp. Windows offer glimpses of the outside ambiance.
Cabin in Mendon
4.85 out of 5 average rating, 249 reviews

THE CABIN....a Vermont log home

JeffRating, 5 stars1 month ago
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.
Guest favorite
An outdoor pool is surrounded by lounge chairs and red umbrellas. Lush green trees frame the space, creating a serene environment. A small poolside shed is visible, adding functionality to the area.
Condo in Killington
4.75 out of 5 average rating, 92 reviews

Still 89 Trails Open, Low, Low Rates

RyanRating, 5 stars1 month ago
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.
Superhost
The spacious living area features a stone fireplace flanked by comfortable seating arrangements. Large windows provide natural light, creating a warm atmosphere. A wooden mantle is adorned with decorative skis, while a coffee table complements the seating. Light fixtures add a soft glow to the room.
Home in Killington
4.84 out of 5 average rating, 88 reviews

Killington Racquetball House

EmersynRating, 5 stars3 weeks ago
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.
Top guest favorite
A warm hot tub is presented against a snowy landscape, surrounded by trees bare of leaves. The distant view of the reservoir is framed by the serene white of winter, inviting relaxation and tranquility.
Home in Chittenden
5 out of 5 average rating, 8 reviews

Modern Retreat next to Mountain Top Inn,Killington

MaddyRating, 5 stars2 months ago
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!
Top guest favorite
A modern home is set amidst natural greenery, featuring a wood-paneled exterior. The structure showcases multiple oversized windows on each floor, allowing for ample light. Surrounding grass and trees create a serene environment, enhancing the sense of privacy and tranquility.
Home in Plymouth
5 out of 5 average rating, 16 reviews

Luxury Modern Cabin near Okemo & Killington

TariQRating, 5 stars1 month ago
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!
Top guest favorite
A spacious hot tub emits a soft blue glow in the dark, surrounded by mist. The area is accented with a wooden deck, and a staircase provides access to the tub. Soft lighting enhances the peaceful ambiance of the outdoor space.
Home in Warren
4.97 out of 5 average rating, 39 reviews

Private Home with Hot Tub 1 mile from Sugarbush

ThomasRating, 5 stars1 month ago
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!
Guest favorite
Home in Newport
4.93 out of 5 average rating, 57 reviews

Crescent Lake home swim, golf and hike

SaraRating, 5 stars2 months ago
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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Stockbridge