
Vacation rentals in Woodstock
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Top-rated vacation rentals in Woodstock
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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.

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.

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!

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

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

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

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.

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.

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.

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.

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*

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
Other great vacation rentals in Woodstock

LUXE Forest Retreat

Beautiful Woodstock Home-Perfect for entertaining

Luxe Barn Retreat in Woodstock

Cozy 4-season Cabin on Pond - "East Cabin"

Yurt In The Woods - Private Refuge

Private Barn On a Hilltop in Fairlee, Vermont

Birdie's Nest Guesthouse

The Berghüttli: The Coziest Cabin in Vermont
When is the best time to visit Woodstock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ933 | ﺩ.ﺇ992 | ﺩ.ﺇ933 | ﺩ.ﺇ845 | ﺩ.ﺇ959 | ﺩ.ﺇ1,010 | ﺩ.ﺇ1,061 | ﺩ.ﺇ1,116 | ﺩ.ﺇ1,080 | ﺩ.ﺇ1,161 | ﺩ.ﺇ922 | ﺩ.ﺇ1,065 |
| Avg. temp | -7°C | -6°C | 0°C | 7°C | 14°C | 18°C | 21°C | 20°C | 15°C | 9°C | 3°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.
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!
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