
Holiday rentals in Woodford
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Top-rated holiday rentals in Woodford
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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
Bright airy cottage w/ lake view
Chickadee cottage is located in the heart of the Woodford lake community, just across the street from the lake. Plenty to see and do near this mountain retreat. We are a short walk to the beach or continue on to miles of hiking trails. In the winter nordic ski at Prospect Mt. (1 mile) or downhill ski at Mt. Snow (19 miles). Any time of year enjoy casual eating or fine dining in Wilmington, Bennington or use the grill and eat out on the deck. A bonus: Woodford State Park is just down the road.
4.98 out of 5 average rating, 63 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
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!
4.99 out of 5 average rating, 376 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!
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.
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, 167 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, 391 reviewsPopular amenities for Woodford holiday rentals
Stay near Woodford's top sights
Other great holiday rentals in Woodford

Willow Tree Cottage on Peaceful Mountain Lake
4.98 out of 5 average rating, 91 reviews
Cozy, welcoming, Cabin in the woods!
5.0 out of 5 average rating, 11 reviews
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Foliage Haven | Lake & trails | Green Mountain
4.86 out of 5 average rating, 29 reviews
The Cozy Cottage @ Woodford Lake
4.59 out of 5 average rating, 17 reviews
Cozy Cabin & Fun-Filled Barn *VAST access* Mt snow
5.0 out of 5 average rating, 22 reviews
The Old Pine House
4.98 out of 5 average rating, 63 reviews
Green Mountain Getaway
4.94 out of 5 average rating, 66 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
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- Saratoga Spa State Park
- Naumkeag
- University of Massachusetts Amherst
- MVP Arena
- New York State Museum





