
Vacation rentals in Woodstock
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Top-rated vacation rentals in Woodstock
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Sweet apartment near downtown Woodstock
A newly renovated sweet apartment. This is located on the first floor of our house with a completely separate unit and entrance. We do live upstairs. There are granite countertops and the kitchen is equipped for guests to create special meals during their stay. New floors are accenting this warm space. There is one queen bed in a separate bedroom, and a pull out couch in the living room. You will probably hear noise from upstairs. The furnace and water pump are in the bathroom and can be noisy.

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.

forest retreat; off-grid writers cabin
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 (seasonal) 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 Killington, S. Royalton, White River, Lebanon & Hanover NH

Beautiful Timber Frame Retreat
This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

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

Cozy Log Cabin, Relaxing Retreat with 1pm 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 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.

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

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.

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*

Yurt In The Woods - Come to the Yurt.
The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for Weekends. The month of October I require a two night stay. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network AC, Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available June - October

Scandinavian design Cabin hiking trail + hot tub
Welcome to our charming cabin nestled in the heart of the woods, where comfort meets tranquility. This 400 sq. ft retreat is bathed in natural light, boasting high-quality appliances, strong WiFi and thoughtfully curated design furniture to ensure a cozy and memorable stay. Relax in our private Goodland wood burning hot tub. Goodland wood burning hot tub is available 365 days a year. EV charger level 2 available.
Popular amenities for Woodstock vacation rentals
Other great vacation rentals in Woodstock

The Spooner House – A Relaxed Farm Stay in Vermont

Cheerful, Restored 1940s Cape- 5 mins to Woodstock

Fabulous Log Home in the Woods

A Peaceful Brookside Vermont Retreat

A-Frame cabin in the woods

Hot Tub + Gorgeous Views - Green Mountain Getaway

Walk to Woodstock Village Designer Home | Sleeps 8

Vermont Suite @Anderson-Key Farm
When is the best time to visit Woodstock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$57,499 GYD | G$58,545 GYD | G$52,690 GYD | G$48,090 GYD | G$54,572 GYD | G$57,499 GYD | G$60,427 GYD | G$63,563 GYD | G$61,472 GYD | G$67,326 GYD | G$52,063 GYD | G$62,099 GYD |
| 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 190 vacation rentals in Woodstock

Nightly prices starting at
Woodstock vacation rentals start at G$18,818 GYD per night before taxes and fees

Verified guest reviews
Over 7,070 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!
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