
Kid-friendly holiday rentals in Woodstock
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Woodstock
Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.
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Popular amenities for Woodstock family-friendly rentals
Kid-friendly house rentals

Cozy Bow House Perched in Trees w/ Hot Tub & View
The Bow house was a beautiful place and Jen was incredibly hospitable and responsive. This is an amazing place to come and get away from the noise. Everything was so clean and cozy. Would definitely come again!

Beautiful Historic 1909 Library with a Fireplace
We love the library! Stayed here 4 times now. It's a special place filled with history, in a beautiful area with quite a bit to do nearby. The fireplace is lovely and cozy, the bed is super comfortable, the kitchenette has everything you need, and we love that it's dog friendly too. There were even some toys for our pup to enjoy during our stay. Highly recommend for a unique and special getaway!

Romantic Mountain Getaway
Thank you, Bianca, for a wonderful stay in your stylish, clean, comfortable home and beautiful property. We would definitely rate it five stars and highly recommend it to others. An extra thank you for accommodating our unplanned family graduation dinner—it meant a lot to us! Sergey and Taya

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!

The Guest House at Sky Hollow
This is my second time staying at one of Jess’s properties - and I’m sure it’s not my last. The property is beautiful inside and out and has everything you need. I was in town for a full week and this place was just what I needed to relax after long work days. I can’t recommend staying at one of Jess’s places enough. You won’t regret it!!
Family-friendly apartment rentals

Bog Mt Retreat Upstairs Suite
Exceptional! Dave and Donna are the best! Beautiful property! Immaculate! Friendly. Beyond highest rating we can give. We will be back! Thank you for everything!

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!!!

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.

The Old Farmhouse
We were just there one night but were comfortable and enjoyed having lots of space. Appreciate that all was as described/expected.

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

Waterfront cottage walk-out suite.
Great place ,The cottage is very clean. It has everything we needed and is the perfect place to relax. The view of the pond is beautiful, and we really enjoyed it . It is a very quiet neighborhood , beautiful surroundings and lovely hosts Ed and Peggy is a wonderful, friendly hosts who was so respectful of our space and privacy. I Had a great time with my daughter thankyou Ed and Peggy for sharing your beautiful Gottage with us We look forward to coming back Lamiya

Your home away from home
Really great, efficient, comfortable lodging on a residential street but in good walking distance to restaurants, coop, and shops downtown. Very easy to find and easy instructions, good communication, all around great place to stay, especially given the reasonable rate! Will return!

Beautiful 1 bedroom apartment with balcony
Pascale was a kind and generous host, who was polite, accommodating, and flexible. The house has a unique aesthetic, part Victorian, part historic farmhouse, and all tastefully decorated. My stay was short and off-season (work trip), so unfortunately I didn’t have enough free time to explore. My hope is to stay here again in the future and take advantage of the walkable proximity to restaurants and the endless outdoor options nearby.
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!

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.

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.

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!!

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.

Hike bike golf 1 bedroom 1 nght Ok shuttle
Great place great stay as always !!
Quick stats about holiday rentals that are kid-friendly in Woodstock
Total rentals
40 properties
Nightly prices starting at
$128 SGD before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
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- Squam Lake
- Stratton Mountain
- Sugarbush Resort
- Okemo Mountain Resort
- Owl's Nest Resort
- Pats Peak Ski Area
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Autumn Mountain Winery
- Fort Ticonderoga
- Dorset Field Club
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Northeast Slopes Ski Tow
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Hooper Golf Course
- Bretwood Golf Course
- Fox Run Golf Club
- Ekwanok Country Club