
House vacation rentals in Rupert
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Top-rated house rentals in Rupert
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Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

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.

Mountain View Getaway
Escape to our cozy, inviting home nestled on the side of a mountain in East Dorset, VT. This peaceful getaway features 2 spacious bedrooms and 1.5 modern bathrooms, perfect for families or couples. Enjoy a fully equipped kitchen, a relaxing living area, and a beautiful backyard with a deck for outdoor dining. Explore nearby hiking trails, skiing, swimming, local attractions, or simply relax in nature's beauty. Easy check-in and check-out. No smoking Well trained pets only No large parties

MOUNTAIN NEST, views, Manchester, hot tub,
Convenient to downtown Manchester's outlet stores and restaurants,golf (equinox golf course 3 miles away) hiking, kayaking and fishing (battenkill river)skiing-Stratton or Bromley, hot tub on full deck with close-up views of Mount Equinox, these mountain views will either make you weep or sing for joy, dines 8 easy, master on main (king bed). This home was intended to bring INSIDE the natural beauty you see OUTSIDE. Complete with vaulted living area and exposed timber beams throughout!

Cozy Home in Poultney, Vermont.
If you are looking for a cozy spot to relax in a small town, with fast internet and easy access to lots of fun activities, this house is it! On the main floor of the house, there is an open layout that includes a library, a small bar, a dining room, a kitchen, a bathroom, and two bedrooms. Downstairs, there is a finished basement that includes a large family area with a huge couch (perfect for movies), a workspace, and a laundry space. Private parking and lots of outdoor space.

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.

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.

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.

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.

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.

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.

Comfortable farmhouse with stunning views
Beautiful old farmhouse built in 1799 located in Danby, Vermont. Close to skiing - Bromley (30 mins), Okemo (35 mins), Stratton (40 mins), Killington (45 mins). Amazing views all year round. 15 mins to the town of Manchester and outlet shopping.
Popular amenities for Rupert house rentals
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Magical Farm Getaway - a must visit!

Steps to Golf and Mountain Biking

Ranch at Mendon Mt Orchards

Adams Farm-"The Little Farmhouse"

SARATOGA GEYSER RETREAT

Contemporary, Warm & Cozy Home mins to Saratoga

The Vermont Barn (Mount Snow)
Weekly house rentals

The Riverside Treehouse

Minutes from Vt. Summer Festival and Ski slops

Lakefront gem

The Lower Hollow House, dip into river in backyard

The Looking Glass, a modernistic escape

Sugar Shack Lodge

Glorious Mountain View in Dorset

Mountain Serenity
Private house rentals

Charming Vermont Retreat

Stratton Summer House | Trails + Swim Holes + AC

Slice of Heaven Cottage on Hedges Lake w/ Boat!

Woodland Tiny Home Hideaway

Home in the Heart of Dorset Village

Vintage Carriage House - step back in time

Little House on the River

Comfortable Two Bedroom Duplex
Destinations to explore
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- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Killington Resort
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Stratton Mountain Resort
- Jiminy Peak Mountain Resort
- West Mountain Ski Resort
- Fort Ticonderoga
- June Farms
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Saratoga Spa State Park
- Bromley Mountain Ski Resort
- Adirondack Extreme Adventure Course
- National Museum of Racing and Hall of Fame
- Gore Mountain
- Rensselaer Polytechnic Institute
- Rivers Casino & Resort





