
Family-friendly vacation rentals in Woodford
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Woodford
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Lakeview Cabin in the Mountains - beautiful
Lovely log sided cabin situated across from Woodford lake with view. Large Great room cathedral ceiling, halfmoon window, pine ceiling & floors, dining table,woodstove, corner gas fireplace, full kitchen. Beautiful ambiance, rustic yet elegant. 3 bedrooms, full bath with clawfoot tub, romantic sleeping loft w sitting area. Basement play area heated with 2 beds for children. Central heat, washer/dryer TV/Roku, ceiling fans. Great getaway for nature lovers, skiers, snowmobilers, hikers. Wifi.
FamilyIndoor spacesBathroom
4.9 out of 5 average rating, 161 reviews
Peaceful VT Chalet w/ Mountain View’s
Our Peaceful chalet has everything you need. A fully equipped kitchen, 3 bedrooms, 2.5 baths, 2 living rooms, elec heat fireplace, outdoor fire pit, washer, dryer, Roku TV’s, great fiber optic internet. Accessible ATV/ snowmobile trails from property. 20 miles to Mt. Snow. Short driving distance to popular golf courses, shops, restaurants,breweries, kayaking, fishing, hiking, white water rafting ect An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).
FamilyIndoor spacesBiking
4.94 out of 5 average rating, 132 reviews
The Hobbit House at June Farms
Watch June Farms on Amazon Prime Video! Enjoy 120-acres of beautiful farmland while you stay in your very own Hobbit house! Nestled in the hills of Hudson Valley, June Farms is a gorgeous animal sanctuary. During your stay, you will be able to meet our Shire horses, Highland cows, spotted pigs, Nigerian dwarf goats, many chickens and ducks! From June 1 - Labor Day, the bar & restaurant is open most days for you to enjoy (check our calendar to be sure). We look forward to meeting you!
KitchenIndoor spacesLocation
4.97 out of 5 average rating, 256 reviews
1 bedroom guest house on dead-end rd
Enjoy a peaceful and private space with 1 bedroom, 1 bath, full kitchen and on site parking. Last house on a dead end rd. 5 min from Southwestern VT Medical Center. 40 min from Mount Snow. 25 min from MassMoca. 15 min walk to Main St where you can enjoy great food and shops. No smoking on premises. Please note there is stairs separating the bedroom (downstairs) and living area, bathroom, and kitchen (upstairs). The stairs are steep and may be difficult for some people.
Indoor spacesKitchenParking
4.81 out of 5 average rating, 154 reviews
See MoCA from your mansion+Sauna!
Large bi-level 4 bedroom apartment tucked away on a hilltop oasis above Mass MoCA (3 mins by foot). 10 mins drive to Williams College & Clark. Whimsically restored (fast Wi-Fi & great water pressure). Fully private with no shared spaces + outdoor Sauna! Your stay’s proceeds allow us to host refugee/immigrant musicians pro bono year-round at @chasehillartistretreat Note: more dates are often available beyond what the calendar shows. Please don’t hesitate to inquire!
FamilyIndoor spacesSleep quality
4.97 out of 5 average rating, 733 reviews
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Escape to our cozy apartment in picturesque Southern Vermont! Featuring a comfortable bedroom, a well-equipped kitchenette, a private bathroom, and a charming dining area, this space has everything you need for a relaxing stay. Enjoy the perfect blend of tranquility and easy access—just a scenic 10-minute drive brings you to North Adams, MA, home to Mass MoCA, MCLA, and plenty of dining and shopping. Book now for the ideal balance of serenity and convenience!
KitchenFamilyBiking
4.88 out of 5 average rating, 360 reviews
Charming Cabin with 2 baths in the Green Mountains
A cozy cabin nestled high up in the green mountains. A perfect getaway on a quiet street. This home is located up on Woodford Mountain. Across the street from Prospect Mountain (cross-country skiing and snow shoeing) and about 25-30 minutes to Mount Snow (downhill skiing). Vast snowmobile trail nearby. Visit the quaint general store nearby or go hiking in Woodford National State Park. At 2,000 ft elevation, the stars are on stage when it's a clear night.
KitchenFamilyValue
4.95 out of 5 average rating, 129 reviews
Cozy Retreat in the Trees
Time travel to 1958 in this architectural gem! This mid-century modern glass and wood cabin is 300 yards away from a charming small lake. The house is NOT on the lake itself, but it is surrounded by trees in a lovely secluded spot. The only heat is a wood stove... but there is a 4-person cedar barrel sauna in the woods that is electric. A classic 1952 Spartanette travel trailer serves as an extra bedroom. This is a true retreat for romance and adventure.
FamilyIndoor spacesCheck-in
4.94 out of 5 average rating, 283 reviews
Airbnb @ Sweet & Savory Farmette
Welcome to the AirBnB situated on a small working farm. You are welcome to tour the grounds to say hello to all the animals. This place is for the birds! No really you will enjoy watching chickens, ducks, emus, geese, guinea fowl, and peafowl. The farm is also home to a herd of beautiful alpaca and resident llama, curious goats, and barn cats. There are working livestock guardian dogs who watch over the herd who will greet you from behind the fence.
KitchenFamilyLayout
4.92 out of 5 average rating, 366 reviews
Suite Sunset 311 Rice Lane Bennington VT
Pet friendly ( additional charge ) Close to picturesque downtown Bennington and many restaurants and attractions. Located in southwest Vermont with easy access to nearby New York and Massachusetts. The famous Bennington Battle Monument provides a free landmark to visit. Enjoy nearby hiking trails and natural areas. Situated on fifty very private acres. Very quiet and peaceful setting. Less than one mile from Bennington College.
KitchenFamilyGetting around
4.97 out of 5 average rating, 122 reviews
The Vermont Farmhouse|Hiking|Dog Trails|Village
The Luxury of Slowing Down — Vermont Style. Leave the rush behind and feel rested, reconnected and renewed at our dog-friendly, beautifully restored 1860s farmhouse. Wide-plank floors, sun-filled rooms and modern comforts create a warm, impeccably clean retreat. Walk across the road into 280 acres of peaceful Mile Around Woods trails, or stroll into historic North Bennington for cafés and shops. It's all right at your doorstep.
Indoor spacesFamilyPets
5.0 out of 5 average rating, 138 reviews
400+ Airbnb Visits: Incredible Mountain Cabin
Our cabin is off the grid, NO running water (read this twice) or indoor bathroom, but it’s comfortable and has been enjoyed by 100’s of Airbnb travelers. There is electricity, but this cabin takes an adventurer in the winter months. Winter Stays take work! Don’t be surprised of shoveling and bringing in your gear! Our reviews speak for how great rental is for people, thank you for considering a stay at our cabin.
FamilyKitchenLocation
4.85 out of 5 average rating, 391 reviewsPopular amenities for Woodford family-friendly rentals
Family-friendly home rentals with a hot tub

Beautiful timber-frame treehouse
KitchenIndoor spacesHospitality
5.0 out of 5 average rating, 124 reviews
Fall Foliage Luxury Cabin & View Autumn Adventures
FamilyIndoor spacesCheckout
4.97 out of 5 average rating, 109 reviews
The House of Pi
Indoor spacesKitchenCheck-in
4.88 out of 5 average rating, 124 reviews
Log Cabin: Amazing Views, River Frontage, Hot Tub
Indoor spacesFamilySkiing
4.99 out of 5 average rating, 320 reviews
Family-friendly 4BR | Pools Hot Tub | Near Mt Snow
KitchenIndoor spacesSleep quality
4.89 out of 5 average rating, 183 reviews
Mid-mod VT Dream Chalet near skiing, lake & forest
Indoor spacesFamilyAmenities
5.0 out of 5 average rating, 137 reviews
Mt Snow Chalet: Peaceful Escape w/Hot Tub
FamilyIndoor spacesLaundry
5.0 out of 5 average rating, 131 reviews
Schoolhouse Spa Retreat on a Vermont Farm
Indoor spacesKitchenView
4.98 out of 5 average rating, 783 reviewsFamily- and pet-friendly home rentals

Quaint One-Story Vermont House with Mountain View
FamilyKitchenNearby
4.88 out of 5 average rating, 155 reviews
The Farm Cottage- Quiet 1BR on Hobby Farm
KitchenIndoor spacesValue
4.98 out of 5 average rating, 264 reviews
Apple Blossom Cottage: A Tiny House
FamilyIndoor spacesAir conditioning
4.94 out of 5 average rating, 1384 reviews
Serene Bus Getaway Among Rolling Farm Land
KitchenIndoor spacesBiking
4.89 out of 5 average rating, 223 reviews
Guest Cottage - Mountain Views, History & Hiking
Indoor spacesFamilyBackyard
4.99 out of 5 average rating, 104 reviews
Netherwood - North Adams Guest House with Views
FamilyKitchenAccess
5.0 out of 5 average rating, 337 reviews
Snug Chalet - Wi-Fi + Close to Mount Snow
FamilyKitchenPets
4.97 out of 5 average rating, 148 reviews
5BR Rustic Mountain Sanctuary Dome Home
FamilyIndoor spacesPets
4.94 out of 5 average rating, 139 reviewsFamily-friendly home rentals with a pool

Hollywood Bungalow in the Berkshires #C0191633410
Indoor spacesKitchenCheck-in
4.9 out of 5 average rating, 242 reviews
Great Amenities-Season Condo gym-sport center-pool
KitchenFamilyHot tub
4.94 out of 5 average rating, 107 reviews
Cozy cottage with pool, walking distance to lake
Indoor spacesFamilyHospitality
4.95 out of 5 average rating, 171 reviews
Silver Brook Cabin
KitchenIndoor spacesValue
4.95 out of 5 average rating, 180 reviews
Winter Dream! The Handle Lodge at Snowtree Condos
KitchenIndoor spacesView
4.99 out of 5 average rating, 136 reviews
Base of M.S. All Seasons Fun. Deck/HotT/Sauna
Indoor spacesFamilyHeating
4.92 out of 5 average rating, 128 reviews
Historic Farm Stay | Heated Pool + Hot Tub
Indoor spacesFamilyWalkability
4.98 out of 5 average rating, 214 reviews
Saratoga Fall Escape | Hot Tub, Fire Pit & Game Rm
FamilyIndoor spacesLayout
5.0 out of 5 average rating, 104 reviewsDestinations to explore
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