
Holiday rentals in Woodstock
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Top-rated holiday rentals in Woodstock
Guests agree: these stays are highly rated for location, cleanliness and more.

Cozy Getaway- Ski, Woodstock, Hanover
Luxurious, well appointed cottage - Beautiful sunrise view located between Woodstock VT and 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

majestic 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

Clean, cozy, beautiful studio in the heart of WRJ.
This beautiful studio is in a new building built in 2021. It is a clean, quiet, place to stay in a building of young professionals. Walking distance to restaurants, bars, art galleries, and all this historic town has to offer. Within a 3-min walk: Tuckerbox, Wolf Tree, Big Fatty’s, Northern Stage. 10 min: King Arthur Baking 10 min: Dartmouth College 15 min: Dartmouth Hitchcock Medical Center 25 min: VT Law School Perfect, cozy place for visiting parents, traveling nurses, professionals, etc.

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

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

Adorable Dog Friendly Cottage w/FIOS
Just 5 miles from Woodstock, this bright two-story cottage sits on a peaceful 20-acre oasis of woods, pasture, and hill views. Especially cozy in winter, it’s quiet, warm, and welcoming year-round. The cottage has two bedrooms (queen upstairs, full downstairs), one bath with shower, and an open kitchen/living/dining area. February stays include a warm Arrival Comfort setup and late checkout. Guests using only one bedroom receive a 10% discount, applied after checkout (not combinable).

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.

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.

Quiet Vermont Farmhouse
Rent a quiet two-bedroom apartment in our 1850's farmhouse in historic Taftsville, Vermont. We are close to the fascinating history, arts, and shopping of Woodstock VT, and near several downhill and cross country ski and snowshoe centers, Marsh-Billings-Rockefeller National Historical Park, and lots of hiking trails, as well as within a short drive of Hanover NH and White River Junction VT. Come enjoy our warm hospitality, wander our gardens, and enjoy our shared patio.

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.

Yurt In The Woods - Private Refuge
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. October 6th and 12th are currently vacant if you want a fall foliage trip. 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 Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available May - October
Popular amenities for Woodstock holiday rentals
Other great holiday rentals in Woodstock

Private Riverside Studio* Upper Valley*Vermont

Beautiful Historic 1909 Library with a Fireplace

Fabulous Log Home in the Woods

Scandinavian design Cabin w/ private hiking trail

Hideaway Cabin by the Stream on 27 Acres

The Looking Glass, a modernistic escape

Cozy Quechee Corner Cabin near Woodstock

Luxury Barn Retreat in Woodstock
When is the best time to visit Woodstock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 218 | € 231 | € 218 | € 197 | € 224 | € 236 | € 248 | € 261 | € 252 | € 271 | € 215 | € 249 |
| 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 holiday rentals in Woodstock

Total holiday rentals
Explore 180 holiday rentals in Woodstock

Nightly prices starting at
Woodstock holiday rentals start at € 51 per night before taxes and fees

Verified guest reviews
Over 7,020 verified reviews to help you choose

Family-friendly holiday rentals
100 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 80 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
180 of Woodstock holiday rentals include wifi 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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