House vacation rentals in Rutland

4.99 out of 5 average rating, 170 reviews

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

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A modern kitchen features a central island with a wooden countertop, surrounded by two stools. White cabinetry and ample counter space are present, with large windows providing natural light and garden views. A variety of appliances and kitchen tools are visible, enhancing functionality.

4.97 out of 5 average rating, 131 reviews

Quechee Ski Haus: Hot Tub, Sauna, & Mtn Views

Hathaway House: an 1850s barn perched on a hill & made into a stunning modern farm-house with panoramic mountain views west, hot tub, sauna, huge kitchen, study, deck, screened porch & fiber internet. Play on the sprawling lawn or ping pong & foosball in the barn. Enjoy dinner by the great room’s fire or grill and eat al fresco on the deck w/ hot tub, surrounded by gardens & woods. Your private retreat, yet 5 min to Quechee, 15 to Hanover, Saskedena, & Woodstock; 30 to Sunapee & Killington base.

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The bright kitchen showcases a spacious island with seating for four at sleek, modern bar stools. Stylish pendant lights hang above, and large windows provide natural light. Ample cabinetry lines the walls, with contemporary appliances positioned for easy access.

4.94 out of 5 average rating, 134 reviews

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.

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4.96 out of 5 average rating, 101 reviews

A sweeping view showcases Mt Ascutney, framed by vibrant autumn foliage. Rolling fields and meadows are seen in the foreground, with varying shades of green and gold. The landscape captures the tranquil essence of nature, inviting outdoor exploration.

Home in West Windsor

Chuck's Place

With plenty of warm days ahead, we're stoked for the upcoming season. Chuck's a private home on 7 sunny acres overlooking Mt Ascutney. Great for hiking, biking, skiing, snowshoeing- or R&R! A note about Airbnb fees: Airbnb shifted their 15.5% guest fees to the host. We had to raise our rate to compensate. We are loyal to offer accessible ski vacations for your friends & family at the cost of a hotel room! Dollars a day at Ascutney or on your Indy/Ikon/Epic pass. Hit up the 20% on longer stays.

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4.97 out of 5 average rating, 139 reviews

A charming red exterior defines the recently built house, surrounded by lush greenery and a clear sky. The spacious porch features rustic columns, while comfortable seating invites relaxation. Large windows ensure natural light fills the interior, offering a connection to the serene outdoor environment.

Home in Windsor

Custom cabin on Mt Ascutney, Fall and Winter Days…

Combining sweeping views of distant hills with privacy and wraparound porches, the Red House is a custom cabin built for couples and smaller families getting away from busy lives. Glorious colors and quiet winter evenings. 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. It awaits the discerning traveler who can do absolutely nothing, yet experience it all!

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The exterior of the house is viewed, showcasing a modern design with a mix of wood and stone accents. A welcoming entryway features a large front door and a small seating area. Surrounding trees contribute to a natural and serene environment.

4.91 out of 5 average rating, 100 reviews

Quechee Vermont Home

Forget your worries in this spacious and serene space. Nestled in the woods, listen to the sounds of nature from the deck, or take advantage of all that the area has to offer for outdoor recreation. Enjoy the outdoor fire pit and spacious deck for entertaining your guests. Each guest rooms has its own private bath, and the primary bedroom features a private outdoor deck. Enjoy the Air Fryer oven, 5-chamber pure drinking water system, soaking tubs at all bathrooms, top-quality cotton linens.

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4.97 out of 5 average rating, 110 reviews

Home in Bridgewater

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!

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4.93 out of 5 average rating, 103 reviews

Home in Reading

Private, Large 4BR home | Pet friendly | 10 Acres

Okemo & Killington Ski House Large 4 bedroom 2.5 bath, 3,000+ sq ft home located close to Okemo Ski Resort and surrounded by 10 acres of land at the end of a private road! This recently renovated home features 3 levels, a large game room, 5 separate sleeping areas and a large covered porch! Enjoy ultimate privacy with proximity to multiple outdoor adventures including skiing, golfing, hiking and mountain biking. Just a short drive to downtown Ludlow and other surrounding stores in Cavendish.

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4.98 out of 5 average rating, 171 reviews

A bright living area is illuminated by large picture windows showcasing panoramic views of rolling green hills. Comfortable seating arrangements include a sofa and armchair, positioned around a wooden coffee table. A cozy fireplace and a projector screen are visible, enhancing the inviting space.

Home in Pomfret

Private Oasis Under 10 Mins from Woodstock

Less than ten minutes from Woodstock Village, this bright, 3 bedroom home is nestled on ten private acres with spectacular views of Pomfret's rolling hills. The open living area features a large picture window, cozy fireplace and fully equipped kitchen. Relax on the spacious deck with dramatic views of Pomfret’s hills. Please read reviews to see what our guests love about staying here: - Beautiful location - Squeaky clean - Fully equipped kitchen - Comfortable beds - Thoughtful amenities

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5.0 out of 5 average rating, 136 reviews

A mid-century modern home set among lush greenery features a stone foundation and large windows. A brick chimney rises above the roofline, while several wooden Adirondack chairs are positioned on a stone patio, providing a relaxing outdoor space to enjoy the surrounding nature.

Home in Cavendish

Midcentury Hillside Retreat - Summer Paradise

Enjoy this peaceful retreat in the heart of the Green Mtns and surrounded by 130+ acres of private woodland. Dramatic field stone fireplace and spectacular panoramic views of Mt Ascutney into New Hampshire from the entire living space. Large chef's kitchen. Private master suite and two guest bedrooms. The perfect get-away for relaxing with family and friends. Exceptional hiking, biking and Connecticut River adventures. Near GMHA and Woodstock. Great restaurants, fun village shopping nearby.

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A dining area is seen through an open doorway, featuring a wooden table surrounded by six chairs. Warm lighting is provided by a chandelier above, while a bowl of flowers centers the table. A patterned rug lies beneath, and cabinetry is visible in the background.

4.98 out of 5 average rating, 179 reviews

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!

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4.98 out of 5 average rating, 189 reviews

A well-appointed bedroom showcases a spacious bed dressed in white linens, complemented by decorative pillows. A wooden bench is situated at the foot of the bed. A large mirror and artful wall decor enhance the serene atmosphere, while natural light enters through a large window.

Home in West Windsor

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.

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Popular amenities for Rutland house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 101 reviews

A bright and airy great room features high wooden ceilings with large windows showcasing mountain views. A spacious sectional sofa is arranged around a colorful area rug, complemented by blue armchairs. Contemporary lighting and artistic decor add to the inviting ambiance.

Home in Springfield

Luxury Mid-Century Modern Vermont Home, Okemo View

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Superhost

4.86 out of 5 average rating, 260 reviews

Luxury Condo Tucked in the Heart of Killington

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4.96 out of 5 average rating, 142 reviews

Home in Springfield

Ski Mountain View Estate

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A spacious living room is illuminated by large windows overlooking the forest. A leather sofa and armchair are arranged around a patterned area rug. A coffee table and side table with modern lamps complete the cozy seating area. A wood-burning fireplace adds warmth to the setting.

4.99 out of 5 average rating, 170 reviews

SugarBear- Pool, AC, Sauna, Gym, Tennis!

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Superhost

The exterior of a cozy ranch house is shown, framed by lush greenery and flowering shrubs. The front porch is accessible via steps, with a teal door welcoming visitors. A pathway leads through the manicured lawn, enhancing the inviting appearance of the property.

Home in Mendon

Ranch at Mendon Mt Orchards

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4.87 out of 5 average rating, 283 reviews

4.89 out of 5 average rating, 141 reviews

Golf and Mountain Biking outside the door!

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4.9 out of 5 average rating, 184 reviews

A spacious ski home is surrounded by snow-covered trees, featuring a modern design with a sloped metal roof. Large windows allow natural light to enter, while a gravel driveway leads to the entrance. This bustling wooded area provides a serene backdrop during winter.

Home in Peru

Beautiful Bromley/Manchester VT Retreat w/hot tub

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4.92 out of 5 average rating, 114 reviews

The spacious great room features a wood-burning fireplace and is furnished with two comfortable sofas and a wooden coffee table. A large flat-screen TV hangs on the wall, and natural light emanates from the surrounding windows. A dining area with a circular table is visible in the background.

Home in Ludlow

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

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Weekly house rentals

4.87 out of 5 average rating, 159 reviews

A comfortable living area is highlighted by a light beige sofa and a round blue ottoman. A flat-screen TV is mounted above a traditional fireplace. Natural light is welcomed by large windows, contributing to a bright and airy feel.

Home in Lebanon

Benton House, Sleeps 10, King Bed Primary

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4.9 out of 5 average rating, 161 reviews

The kitchen features a large island with seating, surrounded by modern cabinetry and appliances. Exposed wooden beams highlight the ceiling, while natural light pours in through windows on two sides. Clear glass shelves display dishware, enhancing the room's clean and functional design.

Home in Reading

Greystone 1830

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4.96 out of 5 average rating, 600 reviews

The uniquely shaped house, adorned with shingles, is surrounded by lush greenery. Large windows reflect the vibrant foliage, allowing natural light to illuminate the structure. The natural stone wall complements the rustic aesthetic, creating a harmonious blend with the wooded landscape.

Home in Fairlee

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

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4.96 out of 5 average rating, 169 reviews

A serene view captures a green field leading to distant mountains, with a weathered barn nestled among trees. A small shrub occupies the foreground, providing a sense of depth. The landscape reflects a tranquil countryside setting.

Home in Bethel

Vermont private retreat with gorgeous views.

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4.95 out of 5 average rating, 133 reviews

A serene lakeside setting is presented, featuring a stone patio bordered by natural boulders. Colorful adirondack chairs in blue and green invite relaxation. A wooden dock extends into the calm water, with trees and hills visible in the distance under a cloudy sky.

Home in Enfield

Quiet lakeside retreat with private dock.

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4.94 out of 5 average rating, 32 reviews

Surrounded by lush greenery, this single-story home showcases a spacious layout with large windows. The patio area is visible, featuring seating for relaxation. The natural landscape extends into the background, providing a serene and private setting within the countryside.

Home in Hartland

Country House 5 Miles from Woodstock Dog Friendly

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5.0 out of 5 average rating, 26 reviews

Home in Hartland

Cozy and Private Hideaway | Hot Tub + Pellet Stove

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5.0 out of 5 average rating, 32 reviews

2 Min Walk to Woodstock Village Mountain Views

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Private house rentals

4.98 out of 5 average rating, 52 reviews

Home in Barnard

The Looking Glass, a modernistic escape

LocationFamilyHiking

4.94 out of 5 average rating, 18 reviews

Designer-Restored 1870 Hideaway on Kedron Brook

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4.88 out of 5 average rating, 43 reviews

Home in Cornish

Cornish-Windsor Bridge Retreat with Amazing Views

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5.0 out of 5 average rating, 43 reviews

Woodstock Village Retreat

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4.95 out of 5 average rating, 81 reviews

Killington Chalet: Hot Tub, Fireplace, spacious 4b

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5.0 out of 5 average rating, 14 reviews

Eclectic Woodstock Retreat | Views, Deck & Firepit

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Superhost

A bright and open living area features large windows that allow natural light to fill the space. A fireplace is positioned against one wall, with comfortable seating arranged around a wooden coffee table, offering a welcoming spot for relaxation. Decorative plants add a touch of greenery.

4.82 out of 5 average rating, 17 reviews

Spacious 4-Bedroom in Quechee VT

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Aerial view of a secluded home surrounded by lush greenery and rolling hills. The property is nestled within a blend of trees and open fields, offering a serene atmosphere. Visible structures include a spacious home with a red roof and a pathway leading up to it.