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Vacation rentals in Woodstock

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Quick stats about vacation rentals in Woodstock

  • Total vacation rentals

    Explore 190 vacation rentals in Woodstock

  • Nightly prices starting at

    Woodstock vacation rentals start at ﺩ.ﺇ 367 per night before taxes and fees

  • Verified guest reviews

    Over 6,910 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

    80 properties have a dedicated workspace

  • Wi-Fi availability

    190 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!

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
Home in Woodstock

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

LocationFamilyComfort

4.99 out of 5 average rating, 170 reviews
Top guest favorite
A charming cottage is set against a backdrop of lush trees, with a deck extending from the front. The warm, orange sky creates a serene atmosphere, casting soft light on the exterior of the house and surrounding landscape.
Guesthouse in Hartland

Cozy Cottage close to central VT&NH Grand Piano!

Luxurious, well appointed cottage - Beautiful sunrise view located between Woodstock VT & Hanover NH. Inspiring treat for musician’s getaway is a fully restored 1929 Steinway. Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer. VERY comfortable queen bed. Romantic getaway in the woods, relax, work in peace, explore the beauty and history of the area. Hiking, biking, fishing, hot air balloon rides and shopping are all close by. Long (90 day) or weekend rental.

ValueLocationQuiet

4.97 out of 5 average rating, 218 reviews
Top guest favorite
A charming cabin stands beneath a clear blue sky, featuring a metal roof and large windows that provide ample natural light. Grassy areas surround the structure, with trees bordering the background, creating a serene rural setting.
Cabin in Royalton

Genuine Vermont Sugar House on 70 peaceful acres.

Stay in this genuine Vermont sugarhouse. Our family took great pride in making Maple Syrup and now we take that same pride in sharing this private piece of Vermont with you, our guests. There are trails that will take you through our 70-acre property including the sugar bush we used for the sugarhouse. Relax in the quiet beauty of rural Vermont. Located near the geographical center of VT. We do welcome friendly housebroken dogs. Please see other details under show more. Part of Three Maples LLC.

FamilyLocationCleanliness

4.99 out of 5 average rating, 266 reviews
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

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

LocationValueDecor

4.98 out of 5 average rating, 120 reviews
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

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates 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 in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

LocationValueIndoor spaces

4.98 out of 5 average rating, 184 reviews
Top guest favorite
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.
Home in Hartford

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!

LocationFamilyOutdoor spaces

4.98 out of 5 average rating, 179 reviews
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

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

ValueFamilyBathroom

4.99 out of 5 average rating, 320 reviews
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

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.

FamilyValueComfort

4.97 out of 5 average rating, 471 reviews
Top guest favorite
Tiny home in Ludlow

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

LocationFamilyAmenities

4.96 out of 5 average rating, 119 reviews
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

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.

LocationValueSkiing

4.98 out of 5 average rating, 312 reviews
Top guest favorite
Home in Woodstock

2 Min Walk to Woodstock Village Mountain Views

Elevated, quintessential New England home in the heart of Woodstock village, named by Condé Nast Traveler as America’s most beautiful town. Just a 2-minute walk to Central Street, Everstead Estates pairs historic Vermont character with modern comfort, sun-filled rooms, and sweeping hillside views. Access to Mt. Peg trail just 2-minutes on foot, Quechee Gorge is a 10-minute drive, and Killington and Dartmouth are 25 minutes away. Ideal in every season.

LocationFamilyComfort

5.0 out of 5 average rating, 31 reviews
Top guest favorite
The rustic log cabin features a two-story structure with a welcoming wooden facade. A spacious front porch is supported by sturdy columns, allowing for outdoor seating. Surrounding greenery enhances the cabin's natural setting, providing a serene environment.
Cabin in Woodstock

Cozy Log Cabin - Relaxing Retreat w/1pm Checkout

Cozy Cabin has 1pm checkout & no additional cleaning fees. We focus on a comfortable, relaxed, Vermont experience. If you’re looking for peaceful, yet accessible location, we are situated on 15 acres located between Woodstock Village & Killington. There’s fiber WiFi, Hulu w/ +Live TV w/local channels, ESPN+, Disney+, Amazon movies & music, & Netflix. The Rec Room has a pool table, darts, lounge, gym & desk for remote work.

LocationFamilyHospitality

4.98 out of 5 average rating, 226 reviews

Popular amenities for Woodstock vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Stay near Woodstock's top sights

Billings Farm & Museum

286 locals recommend

Woodstock Farmers' Market

140 locals recommend

Marsh-Billings-Rockefeller National Historical Park

73 locals recommend

Sugarbush Farm

62 locals recommend

Mount Tom

59 locals recommend

Farmhouse Pottery

34 locals recommend

Other great vacation rentals in Woodstock

Top guest favorite
Home in Barnard

The Looking Glass, a modernistic escape

LocationFamilyBackyard

4.98 out of 5 average rating, 52 reviews
Top guest favorite
Home in Woodstock

Historic House near Woodstock Inn with Porch

LocationValueCheck-in

4.93 out of 5 average rating, 84 reviews
Top guest favorite
Home in Woodstock

Designer-Restored 1870 Hideaway on Kedron Brook

LocationValueSleep quality

4.94 out of 5 average rating, 17 reviews
Guest favorite
Cabin in Woodstock

A Frame Cabin | Pet-Friendly | Woodstock VT

FamilyLocationBackyard

4.9 out of 5 average rating, 82 reviews
Top guest favorite
The red cottage is illuminated softly by string lights, surrounded by trees. Outdoor seating is provided with several red Adirondack chairs arranged around a fire pit, creating a cozy gathering space. The evening sky can be seen peeking through the foliage.
Cottage in Bridgewater

Riverside Cottage - Bridgewater Vermont

FamilyLocationBackyard

4.98 out of 5 average rating, 96 reviews
Top guest favorite
Home in Killington

Killington Chalet: Hot Tub, Fireplace, spacious 4b

ValueFamilyCheckout

4.95 out of 5 average rating, 81 reviews
Top guest favorite
An aerial view showcases a classic farmhouse surrounded by vibrant autumn foliage. The landscape features lush green lawns and a variety of trees, with hints of red, orange, and yellow leaves. The property is complemented by nearby structures and a wide dirt road leading into the scene.
Home in Woodstock

Charming Farmhouse & Gardens, 5 Minutes to Town

FamilyLocationAmenities

4.99 out of 5 average rating, 84 reviews
Top guest favorite
Home in Woodstock

Eclectic Woodstock Retreat | Views, Deck & Firepit

LocationViewCheck-in

5.0 out of 5 average rating, 14 reviews

When is the best time to visit Woodstock?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 1,010ﺩ.ﺇ 1,028ﺩ.ﺇ 925ﺩ.ﺇ 903ﺩ.ﺇ 951ﺩ.ﺇ 988ﺩ.ﺇ 1,061ﺩ.ﺇ 1,116ﺩ.ﺇ 1,080ﺩ.ﺇ 1,183ﺩ.ﺇ 914ﺩ.ﺇ 1,091
Avg. temp-7°C-6°C0°C7°C14°C18°C21°C20°C15°C9°C3°C-3°C

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.

Destinations to explore