Kid-friendly vacation rentals in Woodstock

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Popular amenities for Woodstock kid-friendly rentals

Kid-friendly house rentals

Guest favorite
The uniquely shaped house, adorned with shingles, is surrounded by lush greenery. Large windows reflect the vibrant foliage, allowing natural light to illuminate the structure. The natural stone wall complements the rustic aesthetic, creating a harmonious blend with the wooded landscape.
Home in Fairlee
4.96 out of 5 average rating, 506 reviews

Cozy Bow House Perched in Trees w/ Hot Tub & View

DianaRating, 5 stars4 days ago
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!
Guest favorite
The charming brick exterior of the historic library is framed by green lawns and a stone pathway. The entrance features a covered porch with decorative columns. Lush trees and a bright blue sky enhance the inviting atmosphere of this unique property.
Home in Hartford
4.87 out of 5 average rating, 183 reviews

Beautiful Historic 1909 Library with a Fireplace

AmyRating, 5 stars2 months ago
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!
Top guest favorite
A spacious deck features several black reclining chairs arranged around a white table. Vivid autumn foliage is visible in the background, along with distant mountains and a clear blue sky. The scene invites relaxation in a serene outdoor setting.
Home in Orford
4.98 out of 5 average rating, 123 reviews

Romantic Mountain Getaway

TaisiyaRating, 5 stars4 days ago
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
Top guest favorite
A bright living area is illuminated by large picture windows showcasing panoramic views of rolling green hills. Comfortable seating arrangements include a sofa and armchair, positioned around a wooden coffee table. A cozy fireplace and a projector screen are visible, enhancing the inviting space.
Home in Pomfret
5 out of 5 average rating, 107 reviews

Private Vermont Oasis Under 10 Mins from Woodstock

CathieRating, 5 stars1 month 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!
Top guest favorite
Home in Tunbridge
4.97 out of 5 average rating, 393 reviews

The Barnbrook House

AartiRating, 5 stars3 days 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 favorite
A cozy bedroom features a spacious king bed dressed in a plaid blanket, complemented by decorative pillows. Two bedside lamps provide soft illumination. A wood shelf above the bed holds decorative items. A large window offers a view of the outdoors, dressed with light curtains.
Home in Killington
4.98 out of 5 average rating, 110 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 favorite
A vast green meadow is depicted, dotted with bright yellow wildflowers. In the background, a classic red barn stands amidst rolling hills and gentle mountains, surrounded by clusters of trees and open fields, showcasing the serene landscape of rural Vermont.
Home in Rochester
4.97 out of 5 average rating, 144 reviews

Modern Farmhouse on 25 Acres - Superb Views

BrandonRating, 5 stars2 months ago
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.
Top guest favorite
Adirondack chairs and a small side table are positioned on a spacious deck, offering an unobstructed view of Okemo resort. The winter landscape features snow-covered ground, complemented by a clear blue sky and distant mountain views.
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!

Kid-friendly apartment rentals

Guest favorite
A bright studio apartment includes a comfortable black sofa and a small dining area with two stools. Natural light fills the space through a large window, which is adorned with light curtains. Warm wooden walls complement the smooth, light-colored flooring.
Apartment in Braintree
4.96 out of 5 average rating, 116 reviews

Cozy Cabin Studio

BryanRating, 5 stars4 days ago
This space was perfect for our small family of 4, including our 9 and 7 year old children.. A very quiet and peaceful place. Far enough off the beaten path but still close enough to downtown Randolph and the highway. The space was well stocked with everything needed. Exactly as described. Adria was a very responsive host. We will definitely stay here again!!
Top guest favorite
A two-story, white wooden house is surrounded by lush greenery and shrubs. A porch with a small seating area is visible, along with an air conditioning unit installed on the upper level's front wall. The bright sky and soft clouds provide a picturesque backdrop.
Apartment in Poultney
4.94 out of 5 average rating, 351 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!!!
Superhost
An open living area is shown, featuring a wooden bench, a stylish butterfly chair, and a metal desk with a lamp. Two windows allow natural light to illuminate the space, while a small plant adds a touch of greenery to the decor.
Apartment in Lebanon
4.82 out of 5 average rating, 620 reviews

1200sq.ft AptAt Home on Hanover St

BarbaraRating, 5 starstoday
My college roommate and I had a really nice stay at Chelsea’s place — clean, quiet and easy to get to. I really enjoyed the screened in front porch. We came to the area for a King Arthur Flour 3-day class and it was really convenient for that. Also, plenty of options for eating out (both in Lebanon and nearby Hanover).
Guest favorite
The exterior of a modern home is showcased, featuring a blend of wood and dark siding. Soft light emanates from several windows, highlighting the structural lines. A private entrance is visible at ground level, along with a grassy area leading to surrounding trees.
Apartment in Woodstock
4.88 out of 5 average rating, 128 reviews

New Modern Apartment - Woodstock Village on Mt Peg

TylerRating, 5 stars1 month ago
Great, responsive host & a clean, comfortable space walking distance from town. Recommend 10/10
Guest favorite
The historic Italianate home features a white exterior, with classic green shutters adorning tall windows. A spacious porch is supported by graceful columns, providing numerous seating options. The surrounding yard displays mature trees, enhancing the charm of the property set against a serene backdrop.
Apartment in Middletown Springs
4.89 out of 5 average rating, 255 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 favorite
The exterior of a traditional white house features a spacious covered porch lined with wooden railings and supported by columns. Potted plants and hanging baskets add greenery, while the entrance is framed by multiple windows. A gravel driveway leads up to the porch.
Apartment in Rutland
4.96 out of 5 average rating, 611 reviews

Your home away from home

CatherineRating, 5 starstoday
I have stayed in a lot of Airbnbs. This one was by far the most well equipped, organized and comfortable. It had everything one would need for a stay, short or long term. It was all the more fortuitous as my husband came down with a bad cold and need a day of rest. It was the perfect location for a comfortable rest day.
Guest favorite
A spacious bedroom features a large bed with a decorative canopy and plush pillows. Soft lighting from a chandelier enhances the room's ambiance. A patterned carpet covers the floor, while elegant curtains frame the windows, and a cozy seating area includes a small side table.
Apartment in Claremont
4.89 out of 5 average rating, 151 reviews

Beautiful 1 bedroom apartment with balcony

CarlaRating, 5 stars3 weeks ago
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.
Guest favorite
A charming entrance to a home is highlighted by a welcoming red door, surrounded by greenery and garden features. The driveway accommodates a parked car, while a garage is visible on the left. The roof is designed with multiple angles, adding character to the exterior.
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.

Kid-friendly condo rentals

Superhost
A modern living area is presented with a cozy sofa and decorative throw pillows. A sleek wall-mounted TV rests above a rustic fireplace, with a stylish media console below. Light wood accents and a geometric patterned rug contribute to the inviting decor centered around comfort and relaxation.
Condo 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!
Top guest favorite
The image presents a snowy scene featuring several rustic buildings with sloped roofs. Snow covers the ground and rooftops, with trees lining the background. A hint of ski trails can be seen on the hillside, blending into the foggy atmosphere.
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.
Guest favorite
A cozy living room features a dark leather sofa adorned with decorative pillows. Above the couch, three framed nature-themed art pieces display serene mountain landscapes. A dog rests comfortably on the carpet, with soft lighting from two side lamps enhancing the peaceful ambiance.
Condo in Killington
4.96 out of 5 average rating, 131 reviews

Dog-Friendly Mtn Escape/AC/Pool/

CarlaRating, 5 stars3 weeks ago
Great place! We enjoyed our stay so much that we extended it an extra day. Hosts made it super easy to extend.
Superhost
The living area features a spacious navy sofa adorned with colorful pillows and a light wooden coffee table. A round dining table with black chairs is present, alongside a large mirror and soft lighting that enhance the inviting space. Natural light filters through the sliding doors.
Condo 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
A spacious sleeping area features a large bed with a textured gray coverlet, complemented by two decorative pillows. Flanking the bed are wooden nightstands with lamps. A wall art piece consisting of circular shapes adds visual interest, while natural light filters in through the nearby window.
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 favorite
A modern kitchen with a circular dining table surrounded by four wooden chairs is featured. Stainless steel appliances, including a microwave and oven, are present. A stylish light fixture hangs above the table, while the fireplace and sports equipment are visible in the background.
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 favorite
A living room with a gas fireplace built into a brick facade provides warmth. A comfortable sectional couch faces the fireplace, complemented by a small coffee table. Large sliding glass doors open to a balcony, offering views of greenery outside.
Condo in Killington
4.99 out of 5 average rating, 113 reviews

Cozy Condo next to Resort * AC and Pool *

StephanieRating, 5 stars5 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.
Guest favorite
A cozy living area features a stone fireplace, providing warmth and a focal point in the room. Two brown sofas are positioned around a coffee table. Soft lighting from a nearby lamp creates a comfortable ambiance, complemented by large windows letting in natural light.
Condo in Killington
4.93 out of 5 average rating, 456 reviews

Hike bike golf 1 bedroom 1 nght Ok shuttle

DouglasRating, 5 stars2 days ago
We enjoyed the stay. Good weather so did not need AC. Good thick towels.

Quick stats about vacation rentals that are kid-friendly in Woodstock

  • Total rentals

    40 properties

  • Nightly prices starting at

    $100 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