House vacation rentals 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

Location · Value · TV

Custom cabin on Mt Ascutney, with faraway 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.

Location · Family · Checkout

Quechee Getaway Book Your Ski Trip Now

New Build Multi family friendly home near Woodstock, Killington and Dartmouth – Sleeps 12, Modern Aesthetic, Private Porch & Fire Pit Escape to this stunning modern ski home, just 25 minutes from the Skyship Gondola of Killington, Vermont. Whether you're hitting the powder in winter or enjoying the breathtaking foliage and outdoor adventures in the warmer months, this luxurious retreat offers the perfect base for your next getaway. Hike the Gorge or stroll thru the quaint village of Woodstock.

Family · Value · Wifi

Breathtaking Riverfront Retreat w/Mountain Views

Thoughtfully designed to elevate every moment of your Vermont getaway, our home offers a comfortable & uniquely historic experience, along with panoramic views of the beautiful Ottauquechee River. Perfectly nestled between the vibrant towns of Woodstock and Killington, guests have incredible hiking, skiing, golfing, shopping, leaf peeping, delicious dining, and so much more right at your finger tips. Wonderful for families, couples, or small groups looking to explore all that VT has to offer!

Family · Location · Skiing

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.

Family · Location · Amenities

The Willow House: a Modern Vermont Retreat

Just 7 miles (12 minutes ) to the Dartmouth Campus, this newly re-built little house sits beside its own pond on the edge of a sheep pasture. All the comforts of a modern home in 600sqft. Enjoy access to hiking trails and State Forest lands as well as an easy drive to world-class skiing an hour away and all that the Dartmouth College community offers just minutes away. This is the best of pastoral Vermont, with outside living-dining space ( south facing deck and north facing screen porch).

Family · Value · Decor

Charming, Cozy Cape

Enjoy the warmth, style, and privacy of this lovely home, located on a hillside above the picturesque White River. Just minutes from restaurants, shopping, cocktail bars, and galleries in downtown White River Junction, and a 10-minute drive to Hanover, NH, and the Dartmouth College campus. Set on an acre of open land with beautiful views and sunsets from the back deck. Central heating to keep you cozy during the fall and winter months. Perfect for couples and families ... and pet-friendly!

Value · Location · Condition

Relaxing Countryside Oasis!

Welcome to our cozy 2BR/1BA cabin, ideal for 6 guests. Relax by the indoor fireplace or outside by the fire pit and hot tub. Listen to the stream from the patio. Fully equipped kitchen and washer/dryer for convenience. Only 10 mins from Dartmouth College and 5 mins to downtown Norwich, VT. Multiple ski resorts within 30-minutes. Perfect for a serene getaway, this cabin offers a blend of comfort, nature, and convenience, ensuring a memorable stay for family, friends, or a romantic retreat!

Location · Value · Amenities

Charming Chester Farmhouse Near VT Slopes

Unplug at our spacious 4-bed Chester farmhouse, a four-season retreat minutes from Okemo, Magic & Bromley. Highlights: *Chef’s kitchen & coffee bar *Fast Wi-Fi, dedicated workspace & Smart TV *Spacious backyard for dining & stargazing *Easy 10–20 min to skiing, hiking & local towns *Pet-friendly, family-ready Spend your days hiking, swimming, leaf peeping, or exploring nearby towns. In winter, hit the slopes, then gather for games and a movie. Book your Vermont getaway today!

Location · Family · Check-in

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.

Location · Value · Decor

Meadow View. 35 acres outside your door!

Meadow View - pet friendly home away from home. 35 acres- including 2 trout ponds and 25 acres of wooded trails (perfect for hiking, cross country skiing/snow shoeing!). Featuring a newly remodeled kitchen and bathroom. Minutes from Mt. Ascutney (trails galore, rope tow in the winter). The unit is perfect spot for couples craving time in rural Vermont or for families/outdoor enthusiasts who want to go mountain biking, skiing, hiking. (Okemo 30 min Killington 45 min)

Location · Family · Skiing

The Guest House at Sky Hollow

This quiet 120 acre hilltop house on an 1800's farm turned homestead offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

Location · Value · Quiet