Holiday rentals with outdoor seating in Rutland

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please SEE: Other Things to

Cozy - Killington 40 min. Woodstock-Hanover-Piano!

Luxurious, well appointed cottage - Beautiful sunrise view located between Woodstock VT and Hanover NH. Inspiring treat for musician’s getaway is a fully restored 1929 Steinway Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer. VERY comfortable queen bed. Romantic getaway in the woods, relax, work in peace, explore the beauty and history of the area. Hiking, biking, fishing, hot air balloon rides and shopping are all close by. Long (90 day) or weekend rental

Custom cabin on Mt Ascutney, sweeping Hill Views

Combining sweeping views of distant hills with complete privacy and wraparound porches on two sides, the Red House is a custom cabin built for couples and smaller families. Surrounded by working farms and within easy reach of trailheads to hike or bike Mt Ascutney, or to visit Woodstock, Hanover, Ludlow and the Upper Valley, the Red House sits among some of the best restaurants in Vermont and awaits the discerning traveler who has earned the right to do absolutely nothing and experience it all.

Adorable one bedroom studio in 1844 farmhouse.

Keep it simple at this peaceful and centrally-located place. We have a beautiful 1844 farm house located in Quechee, that has been in our family for over a hundred years. It is located less than a 1/4 mile from the Quechee Gorge and Antique Mall. The farm includes fifty acres of land and trails with wonderful views of Mt. Ascutney, Killington and more. We also abut the state park which has twelve hundred acres of land. All perfect for hiking, snowshoeing, snowshoeing, biking or just relaxing.

Cozy Bow House Perched in Trees w/ Hot Tub & View

The cozy Bow House is perched up above a lovely valley and boasts large south facing windows, a unique bowed loft and a warm, inviting space to relax. Up a charming dirt road past Brushwood & Fairlee Forests with hiking, biking and ATV trails nearby. Lake Fairlee is a scenic 10 min drive; 15 min to Lake Morey & I-91 and 30 min to Dartmouth College. Enjoy the glow of the rising sun and beautiful views above the fog, unwind in the hot tub surrounded by the magical woods and wildlife of Vermont.

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". A lofted space on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony. For more go to @theloft.vt

Private Modern Cabin w/View of Fields, Hills

Enjoy a modern private cabin in the heart of Vermont's pastoral Upper Valley Region. Combining "Glamping" with the comforts of a permanent structure, the "HakuBox" (Haku means "to exhale") was designed to sit lightly on the land and offer a simple, restorative experience. Note: no shower, but swimming holes nearby! Queen bed, fire pit w/grill, free firewood, Adirondack chairs, picnic table, free coffee & tea, dog-friendly with cable trolley, food & water bowls. $39 pet fee applies.

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

Cabin on the Hill

Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.

Birdie's Nest Guesthouse

Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

The Berghüttli: Glowing Swiss Hut in the Forest

The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.