
Family-friendly holiday 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.
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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).
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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.
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Southern Vermont Home
Beautiful home that offers privacy on over one acre of land. It is only a short drive to the conveniences of downtown shopping, restaurants, Bennington College, and much more. This house is 35 minutes from Manchester's famous outlets, 20 minutes from Williamstown, MA, and 45 minutes from Albany, NY. Bromley and Mount Snow ski areas are 40 minutes. The home has wonderful finishes and you will feel right at home upon arrival. Please come explore Vermont from our country escape!
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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.
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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.
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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.
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Steps to MoCA private house + SAUNA!
Welcome to the Gardener’s Cottage at Chase Hill—the historic estate of the owners of the factory that became MASS MoCA. More than just houses, Chase Hill is an experience: gardens, fire pits, sauna, massages, occasional music rehearsals. Just a 5-minute walk to MASS MoCA, 10 mins by car to Williams & Clark. ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!
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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).
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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.
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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.
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Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
Seven minutes from the Mount Snow lifts, this creekside yurt turns mountain days into sauna nights. Ski, hike or explore Southern Vermont, then soak in the private hot tub, heat up the cedar sauna and settle in by the wood stove. The soaring dome, pool table, PS5, stocked kitchen and pet-friendly setup make it an easy year-round base for couples, families and friends.
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Popular amenities for Woodford family-friendly rentals
Family-friendly home rentals with a hot tub

The House of Pi
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Beautiful timber-frame treehouse
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Schoolhouse Spa Retreat on a Vermont Farm
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Mt Snow Chalet: Peaceful Escape w/Hot Tub
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Fall Foliage Luxury Cabin & View Autumn Adventures
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Mid-mod VT Dream Chalet near skiing, lake & forest
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Log Cabin: Amazing Views, River Frontage, Hot Tub
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Berkshire Mountain Top Chalet
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Family- and pet-friendly home rentals

The Farm Cottage- Quiet 1BR on Hobby Farm
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The Chal-A-Frame Vermont
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Guest Cottage - Mountain Views, History & Hiking
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5BR Rustic Mountain Sanctuary Dome Home
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Cozy VT Barn • Fireplace + Fall Foliage+All Season
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Snug Chalet - Wi-Fi + Close to Mount Snow
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Netherwood - North Adams Guest House with Views
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Apple Blossom Cottage: A Tiny House
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Family-friendly home rentals with a pool

Historic Farm Stay | Heated Pool + Hot Tub
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Cozy cottage with pool, walking distance to lake
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Beautiful rustic woods and fields retreat.
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Town & Country Getaway: Pool Gardens Views 6 Acres
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Modern Cottage between Stratton and Mount Snow VT
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10 Min to Saratoga Track-Pool, Hot Tub, Game Room
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Silver Brook Cabin
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The 1770 House
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Destinations to explore
- New York Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Jersey City Holiday rentals
- Portland Holiday rentals
- Newark Holiday rentals
- Mont-Tremblant Holiday rentals
- Atlantic City Holiday rentals
- Newport Holiday rentals
- Providence Holiday rentals
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- June Farms
- 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
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- Saratoga Spa State Park
- Naumkeag
- University of Massachusetts Amherst
- MVP Arena
- New York State Museum





