Kid-friendly holiday rentals in Stockbridge

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Stockbridge family-friendly rentals

Kid-friendly house rentals

Superhost
Home in Pittsfield
4.91 out of 5 average rating, 171 reviews

Beautiful Mountain Log Cabin with Scenic Views

TannerRating, 5 stars2 months ago
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!
Guest favourite
Home in Killington
4.91 out of 5 average rating, 212 reviews

Luxury Condo Tucked in the Heart of Killington

KennethRating, 5 stars1 week ago
Very nice place easy access to routes 4 and 100 with plenty of things to do
Guest favourite
Home in Barnard
4.99 out of 5 average rating, 147 reviews

The Looking Glass, a modernistic escape

MonikaRating, 5 stars1 week ago
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!
Guest favourite
Home in Bethel
4.94 out of 5 average rating, 100 reviews

Comfortable 3 Bedroom King size Master w/ En suite

ChrisRating, 5 stars3 months ago
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.
Guest favourite
Home in Killington
4.85 out of 5 average rating, 112 reviews

Killington Mountain Farmhouse-5 min to Skiing

LeeRating, 5 stars3 weeks ago
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.
Top guest favourite
Home in Tunbridge
4.97 out of 5 average rating, 392 reviews

The Barnbrook House

AartiRating, 5 stars1 day ago
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.
Top guest favourite
Home in Killington
4.98 out of 5 average rating, 109 reviews

CozyDen - AC, Grill, Bike to Mountain!

GinoRating, 5 stars1 week ago
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!
Guest favourite
Home in Londonderry
4.99 out of 5 average rating, 135 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

GeorgiaRating, 5 stars1 week ago
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

Guest favourite
Flat in Bristol
4.86 out of 5 average rating, 155 reviews

Overlook at the Office

JillRating, 5 stars1 week ago
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.
Top guest favourite
Flat in Randolph
4.99 out of 5 average rating, 181 reviews

Phil's Place: Neat apartment close to downtown

DeborahRating, 5 stars2 days ago
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!
Top guest favourite
Flat in Poultney
4.94 out of 5 average rating, 350 reviews

Cozy Poultney Village Apartment

HollyRating, 5 stars3 weeks ago
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!!!
Guest favourite
Flat in Braintree
4.96 out of 5 average rating, 115 reviews

Cozy Cabin Studio

DavidRating, 5 stars1 week ago
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.
Top guest favourite
Flat in Chittenden
5 out of 5 average rating, 248 reviews

Vermont Country Suite

MichaelRating, 5 stars2 months ago
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!
Top guest favourite
Flat in Randolph
4.99 out of 5 average rating, 209 reviews

Historic Wayside Farm - a working dairy farm

Gail And BillRating, 5 stars2 weeks ago
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.
Guest favourite
Flat in Middletown Springs
4.89 out of 5 average rating, 254 reviews

Apartment in Vermont Historic Home

PadraicRating, 5 stars3 weeks ago
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.
Top guest favourite
Flat in Killington
4.89 out of 5 average rating, 148 reviews

Killington VT Chalet - Lower apartment

JoeRating, 5 stars2 months ago
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

Superhost
Apartment in Killington
4.94 out of 5 average rating, 171 reviews

Renovated unit, prime location! Shuttle on/Ski off

KristenRating, 5 stars3 months ago
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!
Superhost
Apartment in Killington
4.89 out of 5 average rating, 130 reviews

Location + Spa! - Cozy 2BR Condo - Mountain Side

DillonRating, 5 stars2 months ago
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!
Superhost
Apartment in Ludlow
4.84 out of 5 average rating, 130 reviews

Okemo Clock Tower Base Ski-in/Ski-out Condo

StephenRating, 5 stars2 months ago
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.
Guest favourite
Apartment in Killington
4.91 out of 5 average rating, 174 reviews

Renovated 1BR, Walk to Lifts, Covered parking

MitziRating, 5 stars2 months ago
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!!
Guest favourite
Apartment in Rutland
4.94 out of 5 average rating, 108 reviews

Ski on Ski off killington/ Pico mountain condo

TimRating, 5 stars3 months ago
Great location! Condo exactly as advertised, great directions. Host communicated regularly and was extremely helpful, I would not hesitate to stay here again!
Guest favourite
Apartment in Killington
4.94 out of 5 average rating, 258 reviews

AC/Dog-Friendly/Spa Onsite/Pool/Wine Bar

ErinRating, 5 stars1 month ago
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.
Guest favourite
Apartment in Killington
4.93 out of 5 average rating, 198 reviews

Newly renovated ski retreat at Killington

YangRating, 5 stars2 months ago
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.
Top guest favourite
Apartment in Killington
4.99 out of 5 average rating, 113 reviews

Cozy Condo next to Resort * AC and Pool *

StephanieRating, 5 stars3 days ago
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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