Kid-friendly holiday rentals in Windsor County

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Windsor County kid-friendly rentals

Child-friendly house rentals

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
Top Guest favourite
Home in Pomfret
5 out of 5 average rating, 107 reviews

Private Vermont Oasis Under 10 Mins from Woodstock

CathieRating, 5 stars4 weeks ago
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!
Superhost
Home in Stockbridge
4.87 out of 5 average rating, 146 reviews

Escape to Vermont

AdamRating, 5 stars3 months ago
Wesley and Damon’s home was a very cozy place and in a great location to stay at if you’re looking to ski at Killington. My friends and I were very happy this is where we chose to stay.
Guest favourite
Home in Barnard
4.99 out of 5 average rating, 146 reviews

The Looking Glass, a modernistic escape

SandyRating, 5 stars2 weeks ago
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.
Top Guest favourite
Home in Tunbridge
4.97 out of 5 average rating, 392 reviews

The Barnbrook House

PeterRating, 5 stars1 week ago
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.
Guest favourite
Home in Bethel
4.85 out of 5 average rating, 154 reviews

Affordable, private, surrounded by flower gardens

SumanaRating, 5 stars1 month ago
John's place was perfect for us to enjoy three days of much needed family time. We played games sitting in the living room with morning coffee or evening wine. We made some simple meals, cooked fiddle heads. The high speed internet helped my daughter to complete some work. We basically enjoyed the second spring there as the field around the house were filled with tulips.
Top Guest favourite
Home in Ludlow
5 out of 5 average rating, 111 reviews

Stunning Views of Okemo - 3 Bedrooms, 3 Bath Home

AmyRating, 5 stars1 week ago
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!
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!

Kid-Friendly apartment rentals

Top Guest favourite
Apartment in Clarendon
4.95 out of 5 average rating, 309 reviews

Dog heavenly! Private, beautiful and relaxing.

MarindaRating, 5 stars3 weeks ago
Our second stay here was great, river was a little higher but we wanted a peaceful weekend with friends and dogs. Apartment was warm given the unseasonable cold weather and we had all the amenities we needed even dog towels for wet pups. Did not see the host during our stay but she was in contact as needed.
Top Guest favourite
Apartment in Andover
4.98 out of 5 average rating, 429 reviews

Private Hilltop farm apartment

WillowRating, 5 stars3 weeks ago
What a lovely and serene spot to spend a few days in the Mountains of Vermont! Loved waking up to views of horses in the field by the private deck and a breathtaking mountain view. The hosts were kind and communicative. The space was clean and had just the right amount of amenities. Definitely recommend and hope to stay again!
Top Guest favourite
Apartment in Woodstock
4.95 out of 5 average rating, 197 reviews

LOG HOME APARTMENT IN WOODST. VILLAGE 3 night min.

AllieRating, 5 stars2 months ago
We absolutely loved our stay with Bob and Sherry. They were so kind and attentive on the app, providing recommendations and checking in frequently when the weather turned on us. Although we were technically in their home, it still felt very private. The apartment is beautifully done and I’m obsessed with the pine wood everywhere. We would absolutely return and cannot recommend this little place highly enough!
Superhost
Apartment in Lebanon
4.82 out of 5 average rating, 618 reviews

1200sq.ft AptAt Home on Hanover St

Karl AndersRating, 5 stars5 days ago
Easy to find and quiet street. Close drive to Hanover and Lebanon. The living room and bedrooms are very comfortable. We did not use the kitchen except for the provided tea and coffee, but it was clean and spacious.
Guest favourite
Apartment in Lebanon
4.84 out of 5 average rating, 407 reviews

The Old Farmhouse

AllisonRating, 5 stars3 days ago
We were just there one night but were comfortable and enjoyed having lots of space. Appreciate that all was as described/expected.
Guest favourite
Apartment in Hartford
4.89 out of 5 average rating, 138 reviews

Clean, cozy, beautiful studio in the heart of WRJ.

JerodRating, 5 stars1 week ago
This was my first air bnb and it was just like the description everything was perfect.. .the only "GRIPE" I had was i couldn't find if there was a fan in the bathroom.
Top Guest favourite
Apartment in Hancock
4.96 out of 5 average rating, 160 reviews

Suite in the Green Mountains

PatrickRating, 5 stars2 months ago
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!
Guest favourite
Apartment in Woodstock
4.95 out of 5 average rating, 119 reviews

Prospect Place

GordonRating, 5 stars1 month ago
No surprises for us, the apartment was exactly as described by previous renters: spacious, clean, charmingly appointed, and situated in a lovely hillside location with a rear deck that invites residents to put their feet up and relax. Easy walk into Woodstock itself. Brenda and Clay are very friendly and helpful while also being unobtrusive People who take such pride in and care of their property are bound to be good folks.

Child-Friendly Holiday Condos

Top Guest favourite
Condo in Ludlow
4.98 out of 5 average rating, 124 reviews

Main St Escape | Explore Downtown Ludlow

RobertoRating, 5 stars3 months ago
Clean, great location, easy check in/out, and friendly host - would definitely stay again.
Guest favourite
Condo in Killington
4.96 out of 5 average rating, 131 reviews

Dog-Friendly Mtn Escape/AC/Pool/

CarlaRating, 5 stars2 weeks ago
Great place! We enjoyed our stay so much that we extended it an extra day. Hosts made it super easy to extend.
Top Guest favourite
Condo in Killington
4.94 out of 5 average rating, 173 reviews

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

JoeRating, 5 stars3 weeks ago
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.
Superhost
Condo 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
Condo 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!!
Top Guest favourite
Condo in Killington
4.99 out of 5 average rating, 112 reviews

Cozy Condo next to Resort * AC and Pool *

AlexandriaRating, 5 stars1 week ago
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!
Guest favourite
Condo in Ludlow
4.94 out of 5 average rating, 148 reviews

Lovely 1-Bedroom condo with indoor fireplace!

BeverlyRating, 5 stars1 month ago
Such an amazing place. Great location for walking to restaurant. Breath taking views especially the river. Extremely homey feel. We will definitely be back. thank you for your hospitality.
Guest favourite
Condo in Killington
4.93 out of 5 average rating, 455 reviews

Hike bike golf 1 bedroom 1 nght Ok shuttle

ScottRating, 5 stars1 month ago
Great place great stay as always !!

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