
Family-friendly holiday rentals in Woodstock
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Woodstock

Total holiday rentals
Explore 100 holiday rentals in Woodstock

Nightly prices starting at
Woodstock holiday rentals start at $204 NZD per night before taxes and fees

Verified guest reviews
Over 3,840 verified reviews to help you choose

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
100 of Woodstock holiday 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!
Top-rated family-friendly rentals in Woodstock
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

forest retreat; off-grid writers cabin
Secluded rustic charm, circa 1900 cabin in the woods getaway, spend time in nature surrounded by forest, brook, wildlife, hiking trails, fall foliage, mountain biking skiing. Sauna, Cold Plunge, Outdoor Shower & Hot Bath (seasonal) Unwind from the outside world and reconnect with your self or your loved ones and the natural world around you. Loft with real beds, well stocked kitchen, grill, outhouse, Glamping! Close to Woodstock, VT and Killington, S. Royalton, White River, Lebanon & Hanover NH
FamilyIndoor spacesAccess

Cape Cod Home in Woodstock, Pet-Friendly & Wooded
Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please see: Other Things to
Indoor spacesFamilyView

Cozy - Killington 40 min. Woodstock-Hanover-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
FamilyIndoor spacesHiking

Breathtaking Riverfront Retreat w/Mountain Views
Thoughtfully designed to elevate every moment of your Vermont getaway, our home offers a comfortable & uniquely historic experience, along with panoramic views of the beautiful Ottauquechee River. Perfectly nestled between the vibrant towns of Woodstock and Killington, guests have incredible hiking, skiing, golfing, shopping, leaf peeping, delicious dining, and so much more right at your finger tips. Wonderful for families, couples, or small groups looking to explore all that VT has to offer!
Indoor spacesFamilyAccuracy

Weasley's Enchanted Treehouse @ Vermont ReTREEt
Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses
KitchenIndoor spacesNearby

THE LOFT, stunning views from a timber framed barn
Welcome to "The Loft". A lofted space 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. For more go to @theloft.vt
KitchenIndoor spacesWi-Fi

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.
Indoor spacesKitchenOutdoor spaces

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.
FamilyIndoor spacesDecor

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.
KitchenIndoor spacesHospitality

The Berghüttli: Glowing Swiss Hut in the Forest
The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.
Indoor spacesFamilyAccess

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.
KitchenIndoor spacesSleep quality

Scandinavian design Chalet hiking trail + hot tub
This bright, well-designed Scandinavian-style chalet is the perfect cozy retreat. Nestled in the woods on a plot of 20+ acres, it offers scenic views and a private hiking trail leading to beautiful vistas, transforming into a winter wonderland for skiing adventures, a summer paradise for outdoor relaxation, and a vibrant canvas for leaf peeping during Vermont's stunning fall foliage season. Goodland wood burning hot tub is available 365 days a year.
KitchenFamilyAccuracy
Popular amenities for Woodstock family-friendly rentals
Family-friendly home rentals with a hot tub

Alpine Reflection + Hot Tub
Indoor spacesFamilyDecor

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board
Indoor spacesKitchenDecor

The Overlook - Views | Hot Tub | Fire Pits | Games
FamilyIndoor spacesValue

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

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
FamilyIndoor spacesQuiet

Modern Cabin with Outdoor Spa on Vermont Farm
Indoor spacesFamilyCondition

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub
Indoor spacesKitchenHiking

Luxury Glass Tiny House - Mountain View + Hot Tub
KitchenFamilyParking
Family- and pet-friendly home rentals

The Guest House at Sky Hollow
Indoor spacesFamilyDecor

Cottage 5 miles from Woodstock-Dog Friendly w/FIOS
KitchenIndoor spacesAir conditioning

Genuine Vermont Sugar House on 70 peaceful acres.
FamilyKitchenAccuracy

Treehut - Secluded Treehouse in the Forest
KitchenFamilyCleanliness

Meadow View. 35 acres outside your door!
KitchenFamilyCleanliness

Yurt In The Woods - Come to the Yurt.
FamilyIndoor spacesNearby

Vermont private retreat with gorgeous views.
KitchenIndoor spacesSkiing

Prospect Place
FamilyKitchenAccess
Family-friendly home rentals with a pool

SugarBear- Pool, AC, Sauna, Gym, Tennis!
Indoor spacesFamilyHeating

Cozy Quechee Cabin near Woodstock and Killington
FamilyKitchenHospitality

Dream Catcher Farm
Indoor spacesKitchenCheck-in

Serene Top Floor Condo (resort style amenities)
KitchenFamilyAccess

Golf Hike 1 bedrm 1 night ok Pico free shuttles
KitchenIndoor spacesHiking

Cozy Vermont Antique Sugar House with Fireplace
KitchenFamilyDecor

Luxury Condo Tucked in the Heart of Killington
KitchenFamilyHiking

AC | Dog-Friendly | Bike, Hike & Relax
KitchenFamilyCheck-in
When is the best time to visit Woodstock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $695 NZD | $686 NZD | $606 NZD | $535 NZD | $553 NZD | $621 NZD | $570 NZD | $596 NZD | $621 NZD | $686 NZD | $601 NZD | $652 NZD |
| 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 |
Destinations to explore
- New York City Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Portland Holiday rentals
- Mont-Tremblant Holiday rentals
- Providence Holiday rentals
- Newport Holiday rentals
- York County Holiday rentals
- Hotel rooms Woodstock
- Apartment rentals Woodstock
- Bed and breakfasts Woodstock
- Rentals with pools Woodstock
- Cottage rentals Woodstock
- Cabin rentals Woodstock
- Waterfront rentals Woodstock
- House rentals Woodstock
- Condo rentals Woodstock
- Rentals with a patio Woodstock
- Chalet rentals Woodstock
- Rentals with breakfast Woodstock
- Villa rentals Woodstock
- Rentals with a hot tub Woodstock
- Pet-friendly rentals Woodstock
- Family-friendly rentals Windsor County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Okemo Mountain Resort
- Squam Lake
- Stratton Mountain
- Sugarbush Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth College
- Tenney Mountain Resort
- Ragged Mountain Resort
- Fort Ticonderoga
- Hildene, The Lincoln Family Home
- Middlebury College
- Killington Resort
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Squam Lakes Natural Science Center
- Montshire Museum of Science
- Emerald Lake State Park
- Mount Sunapee Resort
- Ice Castles
- Stinson Lake
- Camp Plymouth State Park





