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Vacation rentals in Woodstock

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Top-rated vacation rentals in Woodstock

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
The cozy log cabin is surrounded by snow-covered trees, presenting a warm wooden exterior with a balcony. Snow blankets the ground, creating a serene winter landscape. Large windows offer glimpses of the cabin's inviting interior, surrounded by the calmness of nature.
Cabin in Woodstock
4.98 out of 5 average rating, 206 reviews

Cozy Log Cabin, Relaxing Retreat with 1p Checkout

Cozy Cabin doesn’t charge an additional cleaning fee and offers a late 1pm checkout to our guests! We focus on a comfortable, relaxed, Vermont experience. If you’re looking for a peaceful, yet accessible location, we are situated on 15 acres located between Woodstock Village & Killington. There’s fiber WiFi, Hulu with Starz, MAX, +Live TV w/local channels, ESPN+, Disney+. Also Amazon movies & music, Netflix & Peacock. The Rec Room has a pool table, darts, lounge, gym and a desk for remote work.

Top guest favorite
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
4.96 out of 5 average rating, 545 reviews

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.

Top guest favorite
Treehouse in Moretown
4.98 out of 5 average rating, 118 reviews

4-Season Treehouse @ Bliss Ridge; Best Views in VT

thermostat control! LUXURY! 1-of-a-kind, 5⭐️Interior bathroom, @Bliss Ridge - 88acre, OG farm, private estate surrounded by 1000s acre of wilderness. NEW SAUNA& cold plunge!!! Our 2 architectural wonders = real treehouses, built withIN the living trees, not stilted cabins. Equipped w. a fabulous yotel fireplace, indoor hot shower / plumbing, fresh mtn spring water, stable access ramp. Our original Dr. Seuss treehouse, "The Bird’s Nest" is open May-Oct. WiFi avail at the barn! Cell svc works!

Top guest favorite
A modern chalet is situated among lush greenery, featuring a sloped roof and large windows. A cozy outdoor seating area surrounds a fire pit on a grassy lawn, inviting relaxation in a natural setting. A storage area for firewood is visible beside the structure.
Chalet in Woodstock
4.98 out of 5 average rating, 113 reviews

Falcon House: VT Chalet w/Sauna, Bike to Village

Welcome to Falcon House! A modern VT chalet w/sauna at the edge of a 60 acre forest ∙ Outdoor Finnish sauna, shower, yoga platform & hiking trails ∙ 5 min to Woodstock village, 20 min to ski Killington ∙ Spotlessly clean, tastefully furnished, well stocked with thoughtful amenities ∙2 bedrooms, 2 full baths. Lofted king master has ensuite +Lower level den w/double futon ∙ Chefs kitchen, fireplace, 2 TVs & WiFi ∙ Brookside deck w/BBQ & dining ∙Follow Falcon House on Social @falcon_house_vt

Top guest favorite
The kitchen area features a large island with seating and modern appliances. Natural wood paneling complements the high cathedral ceiling. Glass doors open to a scenic view of the surrounding hills, providing ample natural light and a connection to the outdoors.
Barn in Woodstock
5 out of 5 average rating, 284 reviews

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". A lofted space on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony. For more go to @theloft.vt

Guest favorite
A rustic cabin with a snow-covered roof and large windows is nestled among bare trees, creating a serene winter scene. The path leading to the cabin is partially covered in snow, with hints of stone visible along the foundation.
Cabin in Sharon
4.92 out of 5 average rating, 288 reviews

majestic off-grid cabin retreat w/sauna & tubs

Secluded rustic charm, circa 1900 cabin in the woods getaway, spend time in nature surrounded by forest, brook, wildlife, hiking trails, fall foliage, mountain biking skiing. Sauna, Cold Plunge, Outdoor Shower & Hot Bath. Unwind from the outside world and reconnect with your self or your loved ones and the natural world around you. Loft with real beds, well stocked kitchen, grill, outhouse, Glamping! Close to Woodstock, VT and South Royalton, 30 mins to Killington VT or Hanover NH

Top guest favorite
A vibrant garden features an array of yellow daffodils and blooming flowers, extending towards the grassy area. In the background, a charming cottage with a brown roof is nestled among lush trees under a clear blue sky, creating a serene country setting.
Cottage in Tunbridge
4.97 out of 5 average rating, 112 reviews

Vermont Hillside Garden Cottage

Cozy converted artists’ studio, tucked in the hills at the end of a country road. Open the French door to views of a sprawling garden and rolling fields, alight with fireflies in the spring and bursting with color in the fall. Warm yourself by the wood burning stove after winter fun or unwind with a local microbrew by the fire pit, listening to the Whippoorwills on a summer evening. Beautiful in all seasons, this modern, comfy cottage is the perfect place to get away from it all.

Top guest favorite
The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.
Cottage in Windsor
4.97 out of 5 average rating, 428 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Top guest favorite
A unique treehouse is seen perched among tall trees, with a blend of rustic wood siding and large windows that reflect the surrounding greenery. The structure stands elevated from the ground, supported by slender pillars, blending harmoniously with the natural forest environment.
Treehouse in Hancock
4.98 out of 5 average rating, 151 reviews

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling perfect for any admirer of a beloved wizarding world, or anyone who just truly appreciates a isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled among the branches of several maple trees, providing a magical and secluded escape from the hustle and bustle of everyday life.

Top guest favorite
A cozy cabin is nestled among the trees, showcasing a rustic wooden exterior with large windows. It overlooks a gentle slope covered in green grass and wild plants, with sunlight filtering through the canopy above, creating a serene and inviting atmosphere.
Guesthouse in Woodstock
4.98 out of 5 average rating, 278 reviews

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.

Top guest favorite
A modern house with wooden exterior is shown from an elevated perspective, surrounded by autumn foliage. A hot tub is positioned on a spacious deck, which includes a seating area with four chairs and a small table. Scenic mountain views and vibrant trees enhance the natural setting.
Tiny home in Warren
4.99 out of 5 average rating, 280 reviews

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

Guest favorite
An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.
Cottage in Shaftsbury
4.98 out of 5 average rating, 727 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 250 acre property.

Popular amenities for Woodstock vacation rentals

When is the best time to visit Woodstock?

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Avg. priceﺩ.ﺇ933ﺩ.ﺇ992ﺩ.ﺇ933ﺩ.ﺇ845ﺩ.ﺇ959ﺩ.ﺇ1,010ﺩ.ﺇ1,061ﺩ.ﺇ1,116ﺩ.ﺇ1,080ﺩ.ﺇ1,161ﺩ.ﺇ922ﺩ.ﺇ1,065
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Frequently Asked Questions

  • What are the best places to stay in Woodstock?

    Explore vacation rentals around the village center for classic architecture and easy access to cafés, galleries, and local shops. Neighborhoods near the river and covered bridge are also frequently suggested for their scenic charm.

  • What are the best things to do in Woodstock with kids?

    Families often enjoy hands-on learning at Billings Farm & Museum, gentle walks on nature trails, and maple sugaring demonstrations in season. The village green and local playgrounds provide plenty of open space to play.

  • What are some of the best things to do in Woodstock?

    Stroll Main Street for boutiques and local art galleries, explore Marsh-Billings-Rockefeller National Historical Park, or take in the scenery along the covered bridges. The area has seasonal farmers markets, hiking, and maple tasting experiences.

  • How is the weather in Woodstock?

    Winters are cold and snowy, with temperatures around 10–35°F (-12–2°C), while summers are warm, reaching 77–82°F (25–28°C). Spring and autumn bring crisp air, vibrant foliage, and moderate rainfall.

  • When is the best time to visit Woodstock?

    Late spring and autumn are often recommended for blooming flowers and colorful foliage. Summer is popular for outdoor activities and community festivals, while winter draws visitors seeking snow-covered scenery.

  • What are the best places to visit in Woodstock?

    Explore Marsh-Billings-Rockefeller National Historical Park for nature and history, discover Billings Farm & Museum, or stop by the Middle Covered Bridge. The village green is a favorite gathering spot year-round.

  • What are some hiking trails in Woodstock?

    Woodstock has well-tended trails at Marsh-Billings-Rockefeller National Historical Park, with routes suitable for different skill levels. Mount Tom’s summit path is often suggested for its wide views and forested setting.

  • What are some family activities we can do in Woodstock?

    Families can experience interactive exhibits at Billings Farm & Museum, picnic near the Ottauquechee River, or join guided programs at local parks. Seasonal wagon rides and maple demonstrations are also frequently available.

  • What are some of the best day trip ideas from Woodstock?

    Explore nearby villages known for antiques or visit a maple sugarhouse for tasting and tours. Hiking in the Green Mountains or discovering local art studios around the region is also frequently suggested.

  • Are there any pet friendly accommodations available in Woodstock?

    Many vacation rentals in Woodstock welcome pets, especially those near village neighborhoods and outdoor trails. Parks and walking paths help make stays comfortable for travelers with animals.

  • What are some local tips for visiting Woodstock?

    Bring sturdy shoes for uneven paths and try to arrive early at popular sites during foliage or festival seasons. Sampling maple treats and chatting with local shopkeepers is a great way to experience village hospitality.

  • What is Woodstock known for?

    Woodstock is known for its historic covered bridges, classic New England village atmosphere, and strong agrarian traditions. Visitors are drawn by maple sugaring, local art, and scenic landscapes.

  • What are the best hidden gems to explore in Woodstock?

    Look for quiet walking paths near the Ottauquechee River or artisanal shops tucked along side streets. Some visitors enjoy less-traveled trails in Marsh-Billings-Rockefeller National Historical Park.

  • What are the best foods to try in Woodstock?

    Locally produced maple syrup, artisanal cheeses, and fresh apple cider are frequently suggested. Bakeries and cafés in the village center often highlight Vermont-grown ingredients in their menus.

  • What should I bring for a trip to Woodstock?

    Pack for changing weather with layers, a rain jacket, and comfortable walking shoes. A reusable water bottle and camera are helpful for outdoor exploration and capturing Woodstock’s scenic views.

  • What is the nightlife in Woodstock like?

    Nightlife in Woodstock is laid-back, with cozy taverns, wine bars, and occasional live music in local venues. Many visitors wind down with fireside drinks or relaxed evenings at cafés.

  • What are the most popular events or festivals in Woodstock?

    Woodstock has community festivals celebrating the seasons, including a frequently suggested holiday wassail weekend in early winter and events around maple sugaring in spring. Summer brings outdoor concerts and art fairs to the village green.

  • Are there family friendly vacation rentals in Woodstock?

    Many vacation rentals in Woodstock are well equipped for families, with flexible layouts and access to outdoor spaces. Homes near the center make it easy to walk to parks, museums, and activities.

Quick stats about vacation rentals in Woodstock

  • Total vacation rentals

    Explore 180 vacation rentals in Woodstock

  • Nightly prices starting at

    Woodstock vacation rentals start at ﺩ.ﺇ367 per night before taxes and fees

  • Verified guest reviews

    Over 6,680 verified reviews to help you choose

  • Family-friendly vacation rentals

    100 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    180 of Woodstock vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Woodstock rentals

  • 4.9 Average rating

    Woodstock stays are highly rated by guests—averaging 4.9 out of 5!

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Woodstock