
Family-friendly vacation rentals in Woodstock
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Top-rated family-friendly rentals in Woodstock
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

90 Day or Weekend Rentals GREAT Piano!
Luxurious, well appointed cottage - Beautiful sunrise view located between Woodstock VT and Hanover NH. Inspiring treat for musician’s getaway is a fully restored 1929 Steinway Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer. VERY comfortable queen bed. Romantic getaway in the woods, relax, work in peace, explore the beauty and history of the area. Hiking, biking, fishing, hot air balloon rides and shopping are all close by. Long (90 day) or weekend rental

Howling Wolf Farm Yurt--A Magical Glamping Retreat
Our 88-acre farm spreads up a steep hillside above the village of Randolph, one mile away. The land is a mixture of open areas where we rotate our sheep flock daily, and wooded land with trails and old stone walls. You might hear the occasional car or truck on a nearby road, but more likely you'll hear our sheep baaing to one another or the cows across the valley trumpeting, or the abundance of birdsong. The energy here is calming and peaceful--we know you will love it as much as we do.

Fairytale cabin at The Wild Farm
Lay in bed and look out the huge picture window at the farm. You might see cats climbing trees, hummingbirds, snowflakes falling, lightning storms and many more beautiful moments. We have a Wolf, don't be alarmed she is as friendly as can be and will greet you and escort you to the cabin. If you like nature, animals, walking in the forest, cuddling up by the wood stove, then this is the place for you. The cabin is surrounded by gorgeous perennial gardens. We look forward to hosting you!

Private Modern Cabin w/View of Fields, Hills
Enjoy a modern private cabin in the heart of Vermont's pastoral Upper Valley Region. Combining "Glamping" with the comforts of a permanent structure, the "HakuBox" (Haku means "to exhale") was designed to sit lightly on the land and offer a simple, restorative experience. Note: no shower, but swimming holes nearby! Queen bed, fire pit w/grill, free firewood, Adirondack chairs, picnic table, free coffee & tea, dog-friendly with cable trolley, food & water bowls. $39 pet fee applies.

Inviting studio apartment above barn in Vermont
This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Ogden's Mill Farm
Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

THE LOFT, stunning views from a timber framed barn
Welcome to "The Loft". The loft is a newly built apartment on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony.

Cabin on the Hill
Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.

Cozy Little Spot (Self Check-in)
Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.

Black haus: a hip, cool house hidden in a forest.
You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

Love Shack Yurt on Star Lake (100% off grid)
Glamping at its finest. Bring everything but the bed. Enjoy sunsets and star gazing lakeside. No running water or electricity. Clean & custom built outhouse for a toilet. You will need to bring bedding, size king. Please note: self cleaning policy. Leave it in great condition for your fellow travelers. Woodstove for heat, provide your own wood. One King Bed with mattresses and top sheet ONLY. IG@YURTlilyPAD

Lovely Treehouse Stay at Wise Pines- NoBo
Wise Pines is a Holistic & Sustainable Inn/Hiker Hostel that offers a unique farm experience. Reconnect with nature at this bedroom on stilts allows you to sleep amongst the trees peacefully. Farm stand food is available seasonally and yoga is available upon request. Explore 40 acres of walking trails through the woods, garden and around a tranquil pond.
Popular amenities for Woodstock family-friendly rentals
Family-friendly home rentals with a hot tub

~The ClubHaus~

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

Scandinavian design Cabin w/ private hiking trail

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

Lower Yurt Stay on VT Homestead

The Quechee Haus: VT Retreat with Outdoor Hot Tub

Secluded tiny house resort - DOG FRIENDLY

Newly renovated private space on Ascutney Trails
Family- and pet-friendly home rentals

Moon Valley Country Retreat no clean fee pets yes

The Cluck House

Beautiful Woodstock Home-Perfect for entertaining

Glamping Cabin with Private Pond and Mountain View

Apple Blossom Cottage: A Tiny House

Meadow View. 35 acres outside your door!

Addie's Place

Quaint 1-bedroom cottage on Blue Ledge Farm
Family-friendly home rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Renovated unit, prime location! Shuttle on/Ski off

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

Epic Views of the Green Mountains

Beautiful Spacious Condo at Killington Resort

Newly renovated ski retreat at Killington

Cozy Vermont Antique Sugar House with Fireplace

Private Suite in the Green Mountains
When is the best time to visit Woodstock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$73,183 GYD | G$76,528 GYD | G$73,183 GYD | G$66,701 GYD | G$72,137 GYD | G$69,837 GYD | G$70,046 GYD | G$73,183 GYD | G$76,319 GYD | G$76,528 GYD | G$77,783 GYD | G$81,965 GYD |
| Avg. temp | -7°C | -6°C | 0°C | 7°C | 14°C | 18°C | 21°C | 20°C | 15°C | 9°C | 3°C | -3°C |
Quick stats about vacation rentals that are family-friendly in Woodstock

Total vacation rentals
Explore 100 vacation rentals in Woodstock

Nightly prices starting at
Woodstock vacation rentals start at G$23,000 GYD per night before taxes and fees

Verified guest reviews
Over 3,720 verified reviews to help you choose

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
100 of Woodstock vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Woodstock rentals

4.9 Average rating
Woodstock stays are highly rated by guests—averaging 4.9 out of 5!
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- Family-friendly rentals Windsor County
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