
Kid-friendly holiday rentals in Stockbridge
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Top-rated family-friendly rentals in Stockbridge
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Popular amenities for Stockbridge family-friendly rentals
Kid-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

The Looking Glass, a modernistic escape
I booked this spot for my birthday/ mother & daughter getaway and was not disappointed! The views were great and the whole place was very relaxing. Angela was quick to respond to any questions that we had. We traveled with my 3 year old rescue dog and he had the time of his life. There was plenty of space for him to run around! We will certainly be back!

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.

Killington Mountain Farmhouse-5 min to Skiing
We really enjoyed our stay. The location was private and quiet. The house is clean and has everything you need for your stay. Communication from the hosts is some of the best I've experienced; we got proactive messages for checkin and checkout, and any questions were answered quickly. It was chilly (for May, 40s) outside during our stay and the simple to use thermostat kept the inside temperature great in the areas of the house we were using. It was just my father and I, so we didn't need to use most of the house. There is plenty of space for a larger group. I would gladly look to stay at Andrew's place again next year if this house is available on the days we come up. thanks for a great stay.

The Barnbrook House
The barnbrook house was lovely, private and rustic. It had everything our family needed as a base to explore VT/NH. The mountain views are sublime and the house is tucked away offering a lot of privacy. As far as amenities, we loved the toy chest, darts board, and den. There’s plenty of space for a family and Dana stocked up the kitchen with coffee and tea. If you need to be in Hanover for events, this location is a 45 minute drive so keep that in mind when planning.

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!

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
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.

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
The apartment was clean and quiet, beds were comfortable. The kitchen is small, but the fridge and freezer are large and we had enough space to prepare simple meals. It was rainy most of our time there and we were glad to have computers with us, as there is no tv. We did not have the pleasure of meeting our hosts but did enjoy watching the farm activity from the windows. There are no views from the apartment other than looking at the barns. There is a table with two chairs outside, but we would have to move it in order to enjoy the views of the mountains and we weren’t sure if that would be OK. Both the heat and the air conditioning worked great and we were very comfortable inside the apartment.

Apartment in Vermont Historic Home
We keep coming back to this beautiful apartment that is both spacious and elegant while feeling homey and cozy. It’s quiet, immaculately clean with a very comfy bed, nice hot shower, everything you need in the eat-in kitchen.

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!
Family-friendly apartment rentals

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!

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.

Cozy Condo next to Resort * AC and Pool *
We loved staying at this cozy condo. We were able to find it easily and get inside without any issues. The bed was the best we’ve encountered in an Airbnb! I loved the small creek behind the condo and sitting on the balcony with my tea listening to it was a wonderful way to start the day. We would definitely come back again.
Quick stats about holiday rentals that are kid-friendly in Stockbridge
Total rentals
10 properties
Nightly prices starting at
$154 SGD 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
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Cochran's Ski Area
- Fort Ticonderoga
- Autumn Mountain Winery
- Dorset Field Club
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Country Club of Vermont
- Baker Hill Golf Club
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Vermont National Country Club
- Fox Run Golf Club
- Lincoln Peak Vineyard
- Adirondack Extreme Adventure Course
- Killington Adventure Center