
Kid-friendly holiday rentals in Stockbridge
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Top-rated kid-friendly rentals in Stockbridge
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Child-friendly house rentals

Beautiful Mountain Log Cabin with Scenic Views
I have been booking a ski trip with my friends for 10 years now, everyone said this was by far the best house we’ve stayed at and I agree! Location, comfort, and price were all perfect! We will absolutely be back!

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.

Modern Farmhouse on 25 Acres - Superb Views
We had a quiet stay at the Farmhouse. Very peaceful and quiet location. Lots of space for our dog to roam. The house is very nice and clean. We enjoyed having coffee and looking out across the fields, reading, and cooking. It’s near the small village of Rochester with a few restaurants and otherwise we explored neighboring towns like Middlebury, Waitsfield, Stowe, and Montpelier.

Killington area home - 4-seasons & hot tub
We had a great time at David's place. The kitchen was well stocked, plenty of firewood, and the hot tub was ready to go. The house was very clean. All the bedrooms had plenty of linens, and extra blankets. We would definitely stay at David's again!
Kid-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
This was our third stay at Phil’s Airbnb and it will not be our last. You can’t find a more spacious beautifully decorated, a kitchen totally equipped with everything you might want. The bed is very comfortable and the shower is great. There is a great restaurant almost next door. What more could you ask for.? You want original art on the walls?? You get that too!! Best place in the area!

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!!!

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.

Canyons Unit: 1 mile to F&W Summer Camp w/ HOT TUB
Our stay here was perfect. Our host made it really easy for us to feel right at home, which we needed after a 3 hour drive. She was very communicative and even went above and beyond to make us feel welcome. It was my second time staying there. I am looking forward to the 3rd.

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!
Child-Friendly Holiday Condos

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!

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!

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!
Amazing experience! Will be back soon!!

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!!

Ski on Ski off killington/ Pico mountain condo
Great location! Condo exactly as advertised, great directions. Host communicated regularly and was extremely helpful, I would not hesitate to stay here again!

AC/Dog-Friendly/Spa Onsite/Pool/Wine Bar
The Woods complex is a peaceful retreat style community. The condo is cozy with fresh, on point decor. The kitchen was a bit tighter than expected but has generous countertop space. The hosts are friendly and responsive. The stairs to get to the condo could be difficult to navigate for people with mobility restrictions.

Newly renovated ski retreat at Killington
Wayne is super nice, friendly, and responsive. He gave me heads up note on check-in day when the main road (Killington Access Road) was closed due to downed trees&wires. He also helped me confirm the parking spot in late night when I arrived late. The place is cozy and clean. There’s a number of good restaurants and taverns nearby.
Quick stats about holiday rentals that are kid-friendly in Stockbridge
Total rentals
10 properties
Nightly prices starting at
$199 NZD 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