House vacation rentals in Rupert

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!

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

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.

The Vermont Farmhouse|Hiking|Dog Trails|Village

Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

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.

The Nest at Birch Quarry

Our home is located mid-way between Dorset and Manchester VT. This mid 70's style home has been remodeled and updated. The rooms are tastefully decorated. New baths, a well appointed kitchen, large dining area, vaulted ceilings, large deck & marble patio w/ fire pit. Private setting surrounded by woods and quarry pond. The access is flat and off a paved road. 3 min to Dorset. 5 min to Manchester. 10 min to VT Horse Show. 15 min to Bromley. 25 min to Stratton.

Killington Retreat | Deck-Fire Pit-Mountain Views!

Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

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.

Waterfront Cabin • Dock • Fire Pit • Kayaks & SUPs

Relax at this private Vermont lakefront getaway on North Bay. Unwind in a bright, comfortable space with a full kitchen, fast WiFi, and cozy bedrooms. Walk a few steps to the water front to enjoy morning coffee on the dock. Perfect for year-round escapes: -Summer (kayaks, SUPs, floating mat) -Fall (foliage, fire pit, hiking trails) -Winter (skiing, snowshoeing, ice fishing) -Spring (deck, hammock, fishing opener).

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.