Family-friendly vacation rentals in Woodford

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.

Kitchen · Indoor spaces · Grill

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).

Indoor spaces · Kitchen · Backyard

The Farm Cottage- Quiet 1BR on Hobby Farm

Welcome to our peaceful 1-bedroom cottage on a small hobby farm, perfect for couples or solo travelers visiting the Bennington area. This cozy space is designed for rest and simplicity. Whether you're in town visiting family, exploring local trails, or just passing through for a few days, you’ll have a comfortable place to unwind and recharge. Thoughtful touches like fresh eggs from our chickens and homemade jams await you, while the cozy setup makes it easy to settle in and feel at home.

Kitchen · Indoor spaces · Quiet

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.

Kitchen · Family · Sleep quality

The Vermont Farmhouse|Hiking|Dog Trails|Village

Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

Family · Indoor spaces · Quiet

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 spaces · Family · Laundry

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.

Family · Indoor spaces · View

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.

Kitchen · Family · Check-in

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).

Family · Kitchen · Getting around

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.

Kitchen · Family · Getting around

Scenic Vermont Studio

This beautiful retreat is halfway between the ski slopes of southern Vermont and the cultural centers of Williamstown and North Adams, MA. The residence is a modern, spacious, basement apartment, part of an 1860 farm house. It has its own private entrance around the back of the house at ground level. Solar garden lights and motion detector lighting will illuminate your path to the apartment.

Indoor spaces · Kitchen · Backyard

Cozy Modern Sugar House with spectacular views.

This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.

Indoor spaces · Kitchen · Hospitality