
Kid-friendly holiday rentals in Stockbridge
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Top-rated family-friendly rentals in Stockbridge
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Kid-friendly house rentals

Luxury Condo Tucked in the Heart of Killington
Very nice place easy access to routes 4 and 100 with plenty of things to do

Private Vermont Oasis Under 10 Mins from Woodstock
Adam and Nicole's house is wonderful! Great view, spacious, and so clean. We all felt very comfortable and cozy. Great amenities, and a nice deck that unfortunately we didn't get to enjoy because of the rainy weather! Still, we enjoyed our stay and didn't let the rain dampen our spirits. Hosts were both very responsive, no issues with check in. Highly recommend if you're looking for something off the beaten path and quiet, but close enough to restaurants and sight-seeing. Thumbs up for sure!

The Looking Glass, a modernistic escape
Overall we very much enjoyed modern rural space. Kiss the Cow farm about 5min drive was amazing& we got most all main food there w/ additional items from Barnard General Store. Spices/ cookware were very good - we brought nonstick pans& 1 knife to supplement. Plenty bowls, measuring cups/spoons, maybe a set of tom collins glasses would be nice albeit stemless wine and rocks glasses available. Needs garlic/onion powder. Tub was amazing/ upstairs bathroom a true getaway/ relaxing space. It was as pictured albeit note spiral staircase &open grated flooring upstairs. Plenty of windows albeit not much cross breeze so think ahead if bring own fan and/or start A/C before get too warm. I would say you must have an SUV year round for this rental - surrounding roads/ driveway are a good distance on rough dirt/gravel - traversable yet a sportier car with low profile tires/ ground clearance would not work. We enjoyed simply walking driveway& East Barnard Rd. Barnard Inn restaurant worth it.

Comfortable 3 Bedroom King size Master w/ En suite
My friend and I had a very nice stay. The home was very clean which is always my biggest concern. The kitchen was well stocked and had everything we needed. Living space was comfortable and we enjoyed the poo table. 35 minutes to Killington and Pico. Would stay again.

The Barnbrook House
The Barnbrook House was like something from a fairytale. It was more spacious than we thought looking at the photos. I loved my stay here, Dana was very communicative and timely. The fireplace was a great feature of the accommodation which we made good use of. I liked how there was an off grid vibe without actually being too far away from modern conveniences like Wifi, TV, AC. I would stay here again.

CozyDen - AC, Grill, Bike to Mountain!
Dan & Holly’s place was fantastic! Although we didn’t spend much time there due our busy schedule whenever we returned we found the place be extremely homey and comfortable! The house was very clean organized and I could find everything I needed. I felt comfortable throughout my stay and really enjoyed the air conditioning at night due to the humid weather lately! 10/10 would stay again!

Stunning Views of Okemo - 3 Bedrooms, 3 Bath Home
I can only say wonderful things about this property! Everything was beautiful both inside and out. The house was very clean and organized and was also extremely well stocked. Anything that we needed we found in this house. And everyone in our group said the beds were very comfortable… which is very important to me! Erik was great with communication and very proactive. He sent us a note about a week before we checked in that had everything we needed to know; it was quite helpful. I highly recommend this home….and as an added bonus, the view is spectacular! You will not be disappointed if you stay here!

Modern 3-bedroom A-frame in Londonderry w/ Pond
We loved our stay here!! It was the perfect getaway for a long weekend. The property is beautiful and private but close to anything that you might need. The kitchen was super well stocked, beds were comfy, and we really appreciated the firewood supply. Nikki & Topher were great hosts - extremely responsive to all questions we had and proactive about check in/check out instructions. Would definitely come back!
Family-friendly apartment rentals

Overlook at the Office
Small but has a fully equipped kitchen, other than the only sink is in the bathroom. The sink is big and it worked fine. The park is 1/2 block away and town is 2 blocks. Comfortable bed and quiet at night. Good restaurants and unique shops in town. Lots of nature trails close by. Be mindful of having the key it could be easy to get locked out. We enjoyed our time in the apartment and definitely would recommend it to anyone who wants to visit Bristol. Thanks for sharing your place with us.

Phil's Place: Neat apartment close to downtown
Great host, the space has everything you need and is walkable to local shops and restaurants. We enjoyed our stay!

Cozy Cabin Studio
Clean, quiet and comfortable, nice to be able to park in garage. Basically farmhouse setting with a herd of cows next door. Note that house was a bit further down the road than the GPS indicated.

Cozy Poultney Village Apartment
We had an exceptional stay at this Airbnb! It was perfect for two people with plenty of room. It was so cozy. We loved the Vermont specific decor. The ingredients for pancakes and the basic ingredients in the fridge were a thoughtful touch. I could not recommend staying here more!!!

Vermont Country Suite
Cindy and Doug were phenomenal hosts and their suite was so lovely to spend the weekend in while skiing at Killington. Their suite was very clean and cozy, and they went above and beyond to make our experience a great one. They provided homemade banana bread, fresh fruit, snacks, coffee, and even left us a bottle of champagne to celebrate our anniversary. This was one of our favorite airbnbs we’ve ever stayed at, and we hope to stay here again on future trips!

Historic Wayside Farm - a working dairy farm
Outstanding accommodations with comfortable and immaculate rooms. The owners are wonderful and gave us a tour of their farm. We feel so grateful to them for their hard work and dedication to producing organic milk and vegetables. We saw with our own eyes how kind and caring they were to their cows and other farm animals.

Killington VT Chalet - Lower apartment
Can't say enough! Steve was quick to have information and respond. His knowledge of the area is massive and he knows all the great spots to go. Their place was perfect and everything you'd expect from the pictures and description. During our stay we got a large ice storm. Some locals called it the worst ice storm since 1996. Steve was texting me throughout the storm to make sure we were ok and had power and internet. He asked if there was anything he could do for us... And he was located hours away.. Steve and LA went above and beyond in so many ways.. Their place will be the first place I look to stay on return trips!

Suite in the Green Mountains
This was our second, month+ long, stay at Dick & Dorothy's place. It was perfect for the two of us. The internet was reliable with fast speeds which worked great for remote work with zero issues for video calls. They are great hosts and respond quickly to any questions. They apartment is only about 100 yards off of VT 100 and has easy parking which was plowed quickly after any snowfall. There are plenty of options for ski/snowboarding/XC in every direction! Thank you!
Family-friendly apartment rentals

Dog-Friendly Mtn Escape/AC/Pool/
Great place! We enjoyed our stay so much that we extended it an extra day. Hosts made it super easy to extend.

Renovated unit, prime location! Shuttle on/Ski off
This was our second time staying at Caitlyn’s condo in Killington, we chose it again for a reason !! The vibe of the condo is super relaxing, the decor is thoughtful and cool. The fire place makes coming back after a day on the slopes so cozy! We love coming to Killington and this condo is so close to the snowshed lot, it’s perfect!

Bright Ski on/off Condo Full Kitchen-Free Shuttle!
Couldn’t have asked for more. Cozy, clean and such a comfortable place to stay and exactly what was described in the listing. I’ll certainly be booking again! Tricia’s communication was perfect, everything very clear and didn’t have to reach out with extra questions.

Location + Spa! - Cozy 2BR Condo - Mountain Side
We had an amazing stay at this place! The location was perfect—just a short walk to all the incredible relaxation amenities like the pool, steam room, and sauna, which made our trip feel like a true escape. Going for a walk while taking in the views of the mountains were absolutely stunning and made every morning feel special. The unit itself was spotless and had everything we needed for a comfortable, short stay. The kitchen was well-stocked, the bed was cozy, and everything felt thoughtfully arranged. It was the perfect home base for exploring Killington and unwinding after a day of adventure. Would absolutely recommend and may come back during the Peak of the Snow Sport Season!

Okemo Clock Tower Base Ski-in/Ski-out Condo
We loved it. Although it’s not the newest or fanciest condo the location can’t be better right at the Clocktower Base. Our family of for had an amazing time snowboarding and exploring the area. Great restaurants close by and we will definitely be back next year.

Renovated 1BR, Walk to Lifts, Covered parking
I took my 13 yo son for a weekend visit to ski Killington for the first time and Gregory’s condo made our stay worthwhile! It was easy to access, clean, and equipped with all necessities. We will be sure to return!!

Cozy Condo next to Resort * AC and Pool *
Claudia was super responsive and the place was amazing!! Within 5 minutes of a lot of great restaurants and very close to great hiking trails. Would love to come back again!

Serene Top Floor Condo (resort style amenities)
Amazing view and cozy vibes. Hot tub and a pool are fun amenities to have. Building has freshly renovated pool and tubs. If you like it there are also sauna pods. So do not forget your swimsuit. It was clean and if you cook there is a kitchen. On top of that it was great to have a balcony with a view. May is a nice time to come even if you are not skiing because it’s not crowded and nature is stunning. And there are plenty of spots for mountain bike. Scott is a great host and local recommendations are helpful and honest. Visit liquid art, if you want a good cup of coffee that’s the right place. Great place!
Quick stats about holiday rentals that are kid-friendly in Stockbridge
Total rentals
10 properties
Nightly prices starting at
₹10,339 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Stratton Mountain
- Sugarbush Resort
- Okemo Mountain Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Cochran's Ski Area
- Dartmouth Skiway
- Fort Ticonderoga
- Dorset Field Club
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Autumn Mountain Winery
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Baker Hill Golf Club
- Ekwanok Country Club
- Vermont National Country Club
- Cozy Cottages & Otter Valley Winery
- Country Club of Vermont
- Montshire Museum of Science
- Adirondack Extreme Adventure Course