
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.
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).
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!
4.97 out of 5 average rating, 256 reviews
Quaint One-Story Vermont House with Mountain View
From our quaint one-story house, you can see a variety of scenery, from the bright changing colors of the leaves in the autumn to the soft piles of snow in the winter. Experience the quiet of the nearby woods, and see roaming animals such as deer or turkey. Make sure to stop at one of the nearby lakes, each of which offers a variety of amenities, and lush scenery. In the winter, keep warm in the cozy living room next to the fireplace, while having a chat with your friends and family.
4.88 out of 5 average rating, 155 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.
4.82 out of 5 average rating, 153 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!
4.97 out of 5 average rating, 732 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.
4.95 out of 5 average rating, 129 reviews
The Gate House--Experience Vermont!
The Gate House is a historic property located at the foothills of Mt Anthony. Built in 1865, the original structure of the house served as the gate house to the Colgate Estate, one of the most beautiful properties in Southwestern Vermont. Our home is just a few short miles to downtown where you can find local restaurants and breweries. We are not far from some of the best skiing/riding in the Northeast at Mt Snow, Bromley, Stratton and Prospect Mountains.
4.98 out of 5 average rating, 166 reviews
Cozy, bright 3-bedroom Cottage with fireplace.
Cozy, spacious brook-side cottage with 3 bedrooms, 2 baths, fully-equipped kitchen, fireplace, and serene, 382-acre country setting. Colorful artwork, designer furnishings, and well-appointed kitchen and bathrooms will make you feel welcome and at home. Historic charm of Bennington ten minutes away. NYC (182 miles); Boston (118); Mt. Snow (32); Prospect Mountain (13). Close to MASS MoCA (22), Tanglewood (49) and Manchester outlets (32).
4.98 out of 5 average rating, 125 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.
4.97 out of 5 average rating, 121 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.
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.
4.85 out of 5 average rating, 390 reviewsPopular amenities for Woodford family-friendly rentals
Family-friendly home rentals with a hot tub

The House of Pi
4.88 out of 5 average rating, 123 reviews
Fall Foliage Luxury Cabin & View Autumn Adventures
4.97 out of 5 average rating, 109 reviews
Beautiful timber-frame treehouse
5.0 out of 5 average rating, 123 reviews
Mt Snow Chalet: Peaceful Escape w/Hot Tub
5.0 out of 5 average rating, 131 reviews
Schoolhouse Spa Retreat on a Vermont Farm
4.98 out of 5 average rating, 783 reviews
Log Cabin: Amazing Views, River Frontage, Hot Tub
4.99 out of 5 average rating, 320 reviews
Mid-mod VT Dream Chalet near skiing, lake & forest
5.0 out of 5 average rating, 137 reviews
Berkshire Mountain Top Chalet
4.93 out of 5 average rating, 193 reviewsFamily- and pet-friendly home rentals

The Farm Cottage- Quiet 1BR on Hobby Farm
4.98 out of 5 average rating, 264 reviews
Guest Cottage - Mountain Views, History & Hiking
4.99 out of 5 average rating, 103 reviews
Netherwood - North Adams Guest House with Views
5.0 out of 5 average rating, 337 reviews
Cozy VT Barn • Fireplace + Leaf Peak+All Season
4.91 out of 5 average rating, 128 reviews
5BR Rustic Mountain Sanctuary Dome Home
4.93 out of 5 average rating, 138 reviews
Snug Chalet - Wi-Fi + Close to Mount Snow
4.97 out of 5 average rating, 148 reviews
Hollywood Bungalow in the Berkshires #C0191633410
4.9 out of 5 average rating, 241 reviews
Serene Bus Getaway Among Rolling Farm Land
4.89 out of 5 average rating, 223 reviewsFamily-friendly home rentals with a pool

Cozy cottage with pool, walking distance to lake
4.95 out of 5 average rating, 171 reviews
Saratoga Fall Escape | Hot Tub, Fire Pit & Game Rm
5.0 out of 5 average rating, 104 reviews
Historic Farm Stay | Heated Pool + Hot Tub
4.98 out of 5 average rating, 214 reviews
Modern Cottage between Stratton and Mount Snow VT
4.97 out of 5 average rating, 113 reviews
Log Cabin Near Stratton/Mt Snow
4.79 out of 5 average rating, 279 reviews
The 1770 House
4.9 out of 5 average rating, 144 reviews
Town & Country Getaway: Pool Gardens Views 6 Acres
4.82 out of 5 average rating, 209 reviews
Slopeside @ Seasons on Mount Snow (Ski-In/Out)
4.92 out of 5 average rating, 105 reviewsDestinations to explore
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- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- June Farms
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Butternut Ski Area and Tubing Center
- West Mountain Ski Resort
- Thacher State Park
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Hudson Chatham Winery
- Rensselaer Polytechnic Institute
- Mount Monadnock
- Emerald Lake State Park
- Bromley Mountain Ski Resort
- Saratoga Spa State Park
- Naumkeag
- University of Massachusetts Amherst
- MVP Arena
- New York State Museum





