House holiday rentals in Woodstock

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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4.97 out of 5 average rating, 107 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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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, 133 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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4.93 out of 5 average rating, 102 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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4.96 out of 5 average rating, 596 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

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.

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4.98 out of 5 average rating, 168 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, 134 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, 175 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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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, 129 reviews

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

Hathaway House: an 1850s barn perched atop a hill & remade into a stunning modern farm-house with deck onto panoramic mountain views west, hot tub, sauna, huge kitchen, study, porch & fiber internet. Play on the sprawling back lawn or ping pong & foosball in the game room. Enjoy dinner by the fire. Or, in summer, grill on the well appointed deck w/ hot tub and gardens. Nature surrounds this private retreat, yet 5 min to Quechee Center, 15 to Hanover, Woodstock; 30 to Killington base.

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4.98 out of 5 average rating, 186 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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4.98 out of 5 average rating, 240 reviews

A rustic cabin is nestled among vibrant wildflowers and lush greenery. A variety of flowers, including purple and yellow blooms, frame the scene, leading the eye towards the charming structure with a classic metal roof and wooden accents.

Home in West Windsor

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)

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4.93 out of 5 average rating, 103 reviews

A historic barn house from the 19th century is surrounded by lush greenery. A large tree stands in the foreground, while the barn's wooden exterior and stone elements create a rustic charm. Various windows allow natural light to enhance the inviting atmosphere.

Home in Hartland

19th Century Bohemian Barn House

This 19th century barn-house has a welcoming, cosy, bright vibe and a funky bohemian flair. It's artsy, comfortable with touch of sophistication. Lots of sitting areas for reading, conversation and chilling out. Great view and backyard stream; perfect for nature lovers. Decks and wonderful outside space for a cook out or enjoying the brook & gardens on a nice day.

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Popular amenities for Woodstock house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 100 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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4.86 out of 5 average rating, 257 reviews

Luxury Condo Tucked in the Heart of Killington

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4.89 out of 5 average rating, 139 reviews

Golf and Mountain Biking outside the door!

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4.88 out of 5 average rating, 280 reviews

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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4.96 out of 5 average rating, 140 reviews

Home in Springfield

Ski Mountain View Estate

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A refreshing pool is visible in the foreground, featuring a blue inflatable shark and a colorful inner tube. A shaded seating area with a large blue umbrella is highlighted by striped chairs. In the background, a charming building peeks through lush green foliage.

4.9 out of 5 average rating, 133 reviews

CountryBear- AC, Pool, Hot Tub, Fire Pit, Grill

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4.93 out of 5 average rating, 249 reviews

A Colonial home is positioned on a green lawn, showcasing a charming brick façade and a classic porch. Large trees provide shade, while an American flag is displayed proudly by the door. Nearby, a design studio is visible, highlighting the spacious front yard.

Home in Keene

The Brick House on Washington Street

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4.91 out of 5 average rating, 181 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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Weekly house rentals

4.97 out of 5 average rating, 137 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, with faraway views

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4.87 out of 5 average rating, 106 reviews

Home in Chester

Charming Chester Farmhouse Near VT Slopes

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5.0 out of 5 average rating, 26 reviews

2 Min Walk to Woodstock Village Mountain Views

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4.93 out of 5 average rating, 83 reviews

Historic House near Woodstock Inn with Porch

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4.93 out of 5 average rating, 15 reviews

Designer-Restored 1870 Hideaway on Kedron Brook

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5.0 out of 5 average rating, 14 reviews

Eclectic Woodstock Retreat | Views, Deck & Firepit

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5.0 out of 5 average rating, 3 reviews

Home in Pomfret

The House on the Hill

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The charming yellow home is set against a backdrop of autumn foliage, showcasing green lawns and a wooden fence. A gazebo is visible nearby, inviting relaxation. The structure features a gabled roof and is oriented towards the scenic landscape.

4.97 out of 5 average rating, 73 reviews

Dana Road House Sunlit VT Country Home w/HotTub

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Private house rentals

A spacious, two-story house with a grey exterior featuring a metal roof. Surrounded by lush green trees, the structure includes multiple windows and a covered entryway. The setting conveys a serene, natural environment, ideal for enjoying the nearby national park.

5.0 out of 5 average rating, 33 reviews

Woodstock VT Family Friendly, Four Season Getaway

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4.93 out of 5 average rating, 40 reviews

VT Farmhouse w/ Pond, Stream, Firepit & 20+ Acres

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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.

5.0 out of 5 average rating, 37 reviews

Pomfret Retreat, near Woodstock

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4.95 out of 5 average rating, 76 reviews

Killington Chalet: Hot Tub, Fireplace, spacious 4b

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5.0 out of 5 average rating, 14 reviews

Cozy Vermont Cabin | Near Woodstock + Quechee

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4.97 out of 5 average rating, 31 reviews

The Westerdale | Woodstock Retreat | Pet Friendly

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The living room features a warm fireplace, surrounded by two rustic chairs made of wood and woven material. A natural area rug covers the wooden floor, while artwork depicting deer heads adorns the wall above the mantel. A soothing lamp casts light in the corner.

4.99 out of 5 average rating, 72 reviews

The DeerBrook, Distinctive Vermont Lodging

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