
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.

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.

Beautiful Woodstock Home-Perfect for entertaining
Newly renovated - 4 bedroom, 3 bath house, perfect for relaxing or entertaining. Close to all that the Woodstock Village and the Upper Valley has to offer. Amazing location! Only 1.5 mi to the Woodstock Green. Explore the property and feast on the blackberries in summer, raid the tomato garden in the late summer/early fall, and pick the wild fall apples for munching or baking. Bring your snowshoes or cross country skis (in winter) or hiking shoes in summer and explore the property and beyond!

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

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.

THE LOFT, stunning views from a timber framed barn
Welcome to "The Loft". The loft is a newly built apartment 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.

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*

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

Black haus: a hip, cool house hidden in a forest.
You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

LUXE Forest Retreat
Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

Private Barn On a Hilltop in Fairlee, Vermont
This carefully renovated barn is located in the hills of Fairlee, five minutes from I-91. A stand-alone private space with two spacious living areas and decks overlooking ponds and the mountains. You're welcome to bring your dog; please note there is a $75 pet fee for the length of your stay. With direct access to extensive hiking trails and minutes from Lake Morey and the Lake Morey Country Club there's lots of fun things to do.
Popular amenities for Woodstock vacation rentals
Other great vacation rentals in Woodstock

~The ClubHaus~

Comfortable cozy cabin in the hills of Vermont!

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

Boulder House - Extraordinary Luxury in the Woods!

Luxury & Privacy in Woodstock - Barn at Rose Hill

Off Grid Secluded Cabin on 37 Acre Farm

The Tiny Home with Barrel Sauna

4-Season Treehouse @ Bliss Ridge; Best Views in VT
When is the best time to visit Woodstock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $254 | $270 | $254 | $230 | $261 | $275 | $289 | $304 | $294 | $316 | $251 | $290 |
| Avg. temp | 20°F | 22°F | 32°F | 45°F | 56°F | 65°F | 70°F | 68°F | 60°F | 48°F | 37°F | 27°F |
Frequently Asked Questions
Where should I stay in Woodstock?
Make yourself at home in Woodstock by choosing from our most frequently booked neighborhoods. We have over 320 vacation rentals in Village of Woodstock, over 10 vacation rentals in South Woodstock, and over 260 vacation rentals in Taftsville.
Are there vacation rentals with a dedicated workspace in Woodstock?
Yes! Work meets play with ease at over 90 vacation rentals in Woodstock featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Woodstock?
Four-legged friends are welcome in Woodstock. Choose from more than 70 vacation rentals for guests traveling with pets.
Are there Woodstock vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Woodstock, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in bed and breakfast rentals in Woodstock?
Experience the best of Woodstock with our bed and breakfast rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Woodstock have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Do hotel rentals in Woodstock have wifi?
Absolutely! We offer over 10 hotel rentals with wifi in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Woodstock have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Woodstock?
Woodstock has more than 60 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Woodstock?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with self check-in, over 70 homes with wifi, over 20 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
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 $100 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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