
House vacation rentals in Rupert
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Top-rated house rentals in Rupert
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The Mushroom House of Manchester Vermont
Welcome to The Mushroom House. Located at the end of a private road, the house is less than 4 miles from Manchester's outlet shopping, gorgeous hiking and unmatched dining. Our property features an open floor plan main floor with a kitchen, dining and living area that neighbors the master bedroom and bath. The back deck is a accented with string lights, a grill and comfortable outdoor furniture. Down stairs has two guest rooms with queens beds, a full bathroom and a den with full futon and tv.
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Country Colonial Home with rolling fields & stream
This wonderful colonial home offers wide open space on 21 acres of rolling fields with paths leading to the Green River. In the summer build your own dam or in the winter cross country ski along the edges of the stream and get a full view of the West Arlington valley. Swearing Hill is located within a mile of an old country store for all types of immediate supplies. The town of Arlington is 5 miles away, and Manchester, Vt. Is 14 miles, offering golfing, shopping, and wonderful restaurants.
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Modern Cabin with Hot Tub & EV Charging Station
Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat
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Cow Barn Lodge
Our home is located in MT. Tabor, Vermont, just off of Route 7, in a country setting with beautiful Mountain views of the Green Mountain National Forest, Dorset and Danby Mountains. The house is an old barn converted into a beautiful spacious home, on 4 acres. Snowmobiling from our place, plus 4 major ski areas less than 30 miles away. Hiking, fishing, swimming, golfing, and the Equestrian horse show are all nearby. as well as shopping in nearby Manchester and Rutland Vermont.
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The Equinox Cottage
The Equinox Cottage is a quick 3 minute drive to the Equinox Hotel and the heart of Historic Manchester Village. Enjoy the shops, outlets, restaurants, cafes, golfing, and relaxed summer vibe. The Cottage is also an easy walk to the trails in the Equinox Pond preserve. Enjoy this pristine wilderness oasis, plus hiking up Equinox Mountain and surrounding trail system without having to step into your car. This peaceful, spacious, serene spot is ideal for summer relaxation.
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Charming Vermont Schoolhouse
Kick back and relax in this calm, stylish space. A beautifully restored schoolhouse circa 1860 welcomes you. Situated on a quiet country road this adorable home on one wooded acre has lovely mountain views and a peaceful setting. Nearby you will find skiing, hiking trails and quaint Vermont towns with shops and restaurants. Manchester and Rutland are 30 min. drives, Dorset is just 20 min. Granville NY has a large grocery store and other shops and is only a 15 min. drive.
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High Oaks Lodge on Cossayuna Lake
Come enjoy a lakeside getaway at, newly constructed, High Oaks Lodge on Cossayuna Lake! Situated 25 miles from Saratoga Springs, NY and 33 miles from Manchester, VT. Amazing views of the lake from the spacious open-concept living room. Relax on the lower deck and make s'mores around the outdoor fire pit. Water access and private dock for your boat just steps away from the house. Use the canoe and kayaks provided to explore the lake.
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Excellent loft style lodge
Winter: Bromley 20 min, Stratton, Okemo Pico 35 min, Killington 40 min. Great hikes on the AP/LT,Homer Stone trails, Little Rock Pond excellent swimming holes minutes to the lake and VSF. . Back to back with Green Mtn National forest. Pets must be pre-approved.. Please add your pet fee in your reservation. A true home away from home. We are 4 season vacation. Grn Mtn National Forest. Minutes to Manchester .
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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.
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Stunning mid-century house on 2.5 private acres
Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.
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The Post Haus - One-of-A-Kind Modern VT Experience
Welcome to The Post Haus! A one-of-a kind, modern Vermont mini cabin in the Green Mountain National Forest. This high-end, mid-century mod getaway offers an indoor wood-burning fireplace, sauna, high-end kitchen, and two acres alongside the beautiful Ball Mountain Brook. Come enjoy our truly special piece of Vermont!
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Modern Cabin ~ 3min to Stratton Resort
Enjoy your stay in this secluded mountain cabin a 3 minute drive to Stratton resort. The cabin offers a lovely space to unwind and relax after a day on the slopes. Hosts are happy to provide local guidance for skiing, shopping, and food. Situated amongst 45 private acres.
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Popular amenities for Rupert house rentals
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington
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Magical Farm Getaway - a must visit!
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Secluded Luxury Stratton Lodge | Heated Pool
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Private pool | Dock | Luxury 3 Bedroom
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Golf and Mountain Biking outside the door!
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Ranch at Mendon Mt Orchards
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SugarBear- Pool, AC, Sauna, Gym, Tennis!
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Contemporary, Warm & Cozy Home mins to Saratoga
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Weekly house rentals

Cozy Contemporary Downtown Texaco
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Modern 3-bedroom A-frame in Londonderry w/ Pond
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Ski and Play in Manchester Center!
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MOUNTAIN NEST, views, Manchester, hot tub,
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Quaint Pink House on The Battenkill River
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Mountain View Getaway
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Newly renovated. Minutes to Slopes & Trails
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The Cabin on Main - Manchester, Vermont
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Private house rentals

Lakefront gem
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Home in the Heart of Dorset Village
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Glorious Mountain View in Dorset
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Little House on the River
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Relaxing Lakeside Cottage w/ Dock + EV charger
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The Village Cottage
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Barnside Cottage at Fruition Farm
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SKY COTTAGE
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Destinations to explore
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- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- June Farms
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- West Mountain Ski Resort
- Fort Ticonderoga
- Hildene, The Lincoln Family Home
- Killington Resort
- Fox Run Golf Club
- Rensselaer Polytechnic Institute
- Gore Mountain
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- Saratoga Spa State Park
- Adirondack Extreme Adventure Course
- Massachusetts Museum of Contemporary Art
- National Museum of Racing and Hall of Fame





