A vacation rental in Woodstock will position you to embrace the outdoors, where you can enjoy everything from skiing and snowboarding in the winter months to hiking and swimming during warmer temperatures. Cottages, wood cabins and turn of the century farmhouses are all typical types of Woodstock, Vermont vacation homes.
Choose the perfect vacation rental
Best Vacation Home Deals in Woodstock
Find a rental meeting your expectations among the 285 great vacation rentals from numerous partner websites in Woodstock. HomeToGo immediately compares all of these properties so you can save up to 32%!
Top-Rated Rentals and Accommodations in Woodstock
Recommended Vacation Rentals in Woodstock
Find your perfect vacation rental in Woodstock: from $155 per night
Budget-friendly Vacation Rentals in Woodstock
Vacation Houses With Pools
Make a splash on your next vacation! Over 33% of in Woodstock vacation rentals have a swimming pool.
Dog-Friendly Vacation Rentals
Bring Fido on your next trip and book a stay in one of these pet-friendly rentals in Woodstock!
Best vacation rentals with a balcony
Looking for a home with a balcony? Check out these vacation homes in Woodstock with their own private patios and balconies.
Popular Rental Amenities in Woodstock
Above, you can find the most frequently used filters in Woodstock and the number of properties that include them. Woodstock is the right destination to book a rental if you need internet access during your vacation or you never miss an episode of your favorite show, as the most frequently offered amenities are "Internet" and "Air conditioning." It is also possible to find a property in Woodstock if you want a rental with a jacuzzi as 30 of the listed accommodations there provide "Hot tub."
The Weather in Woodstock
7-Day Weather Forecast in Woodstock
Accommodations for your vacation in Woodstock
Farm-to-Table takes is the star of Woodstock cuisine
New England is famous for its fresh seafood, especially along coastal cities like Boston, but Woodstock Vermont offers farm-fresh options that stand out amongst other inland dining options. Mangalitsa is a newcomer to the Vermont food scene and has high quality foods served in a stylish, wooden interior. The restaurant is known for its remarkable hospitality, seasonal small plates, and their quirky wine list.
Every Friday and Saturday Cloudland Farm serves a farm-to-table dinner featuring a set menu of 2-3 courses. This BYOB restaurant’s menu contains items that are all locally raised and can even be tailored to vegetarian and vegan diets.
Vermont doesn’t exactly conjure up notions of the Caribbean, but Melaza Bistro is changing that. Their fresh ingredients leverage tropical flavors and their menu combines classic New England dishes with bolder nuances to create masterpieces like rum guava glazes, chimichurri steak, and fried green plantains.
Farms and science museums are fun for the entire family
Despite the name, Suicide Six is a family friendly ski resort that’s suitable for a wide range of abilities and ages. With 30% beginner, 40% intermediate and 30% advanced slopes, the entire family can enjoy Vermont’s snow-covered mountains. In addition to skiing, the resort offers snowboarding, and during warmer months, you can mountain bike, hike, or go fly-fishing.
Billings Farm is an operational and educational farm located just a short stroll from Woodstock. Take in the farm life exhibits and visit the livestock barns that house sheep, horses, and dairy cattle. The restored and fully-furnished farmhouse was originally built in 1890 and features a formal parlor and a creamery in the basement. In the kitchen, you can watch tour guides demonstrate how late 19th century meals would be prepared on the house’s remarkable wood burning stove.
The Montshire Museum of Science is the perfect way to spend the day as a family, especially during inclement weather. Just a 26min drive from Woodstock, the museum focuses on hands-on activities and exhibits. An outdoor area of the museum focuses on water activities and has 100-acres of nature trails.
Dreamy day trips: Presidential birthplaces and designer outlets
Weston, VT is about 50 minutes from Woodstock. With its historic Village Green, Weston is listed on the National Register of Historic Places. After wandering the quaint town, you can enjoy a show at the Weston Playhouse; it’s the longest-running professional theater in Vermont, and its team produces classic plays, musicals, and modern works all year long.
Located just 21 minutes south of Woodstock is the birthplace of 30th president Calvin Coolidge. Today the Historic Site includes the Coolidge family homestead but also other buildings including his one-room schoolhouse, a barn, and a cheese factory. Feel free to wander the village at any time, or you can pay for entrance into the buildings along with a guided tour during the from May through October.
For a day of shopping, Manchester designer outlets and fine restaurants are just over an hour away. You’ll find high more than 40 retailers at this outlet center, including high end luggage, designer handbags, kitchenware, and plenty of clothing retailers.
Annual festivals highlight the best of Woodstock
Autumn Moon Festival is an annual event held in October, featuring vendors, bouncy castles, face painting, and games. Local historical preservation groups sell wares to raise funds for their organizations, and other vendors display their handcrafted goods including candles, soaps, and condiments made with locally grown ingredients. Performers on stilts wander through the crowd interacting with guests, and musical acts take the stage. If hunger hits you, try the funnel cake and French fries for warm and filling indulgences.
Most beer fanatics know Harpoon Brewery for their award-winning brews and the annual festivals held at their Boston location. But they also have a Vermont brewery that hosts the Harpoon BBQ Festival, an annual cook-off that takes place every July. Think: Beer and BBQ...and lots of it. This two day festival is the backdrop for a competitive BBQ tournament that hosts teams from all over the country.
The Annual Holiday House Tour is held annually and takes place during Christmas. Attendees of this charming annual event are greeted at each house by a host who shares the details and history of the residence. Enjoy a reception with the other house tour attendees at the last stop!
Information about vacation rentals in Woodstock
|🏡 Vacation rentals||284 properties|
|💳 Possible discounts||up to 52%|
|🌙 Nightly prices starting at||$155|
|⭐ Popular amenities||Internet, Air conditioning and TV|
|🐾 Pet friendly accommodations||23 properties|
|🏊 Vacation rentals with pools||99 properties|
Frequently Asked Questions
What is the typical nightly price for a vacation home in Woodstock?
The average accommodation in Woodstock is priced at $155 per night. If you would like to stay in a bed & breakfast, the average price is $351 per night. A house rental Woodstock will cost on average $861 per night.
How many vacation homes are available to book in Woodstock?
Currently there are 284 vacation homes from 5 different providers in Woodstock.
What are the most popular amenities for vacation homes in Woodstock?
Three most popular amenities for vacation home rentals in Woodstock include accommodations that have: Air conditioning, Internet, and TV.
How many vacation rentals with pools are there in Woodstock?
Check out 99 vacation rentals available in Woodstock for renting.
Are dogs allowed in vacation homes in Woodstock?
Sure, currently there are 23 vacation rentals in Woodstock that allow pets and the average nightly rate is $645.
When is it better to travel to Woodstock?
Woodstock has its warmest time of year in July and August, with average nightly prices around $155.
We list offers from thousands of providers, including:
Vacation Destinations Near Woodstock
Vacation Rentals in Killington, VT
Ludlow Vacation Rentals
Warren Vacation Rentals
Stratton Mountain Vacation Rentals
Rupert Vacation Rentals
Manchester, VT Vacation Rentals
Dover Vacation Rentals
Vacation Rentals in Lake George, NY
Wilmington Vacation Rentals
Meredith Vacation Rentals
Laconia Vacation Rentals
Weirs Beach Vacation Rentals
Diamond Point Vacation Rentals
Gilford Vacation Rentals
Moultonborough Vacation Rentals
House Rentals in Lincoln
Vacation Rentals in the Adirondacks, NY
Vacation Rentals in Stowe
Chestertown Vacation Rentals
Schroon Lake Vacation Rentals
Top Vacation Ideas
- Miami Spring Break Hotels & Vacation Rentals
- South Padre Island Spring Break Hotels & Vacation Rentals
- Lake Havasu Spring Break Hotels & Vacation Rentals
- Texas Spring Break Vacation
- Miami Beach Spring Break Hotels & Vacation Rentals
- Romantic Getaways in Florida
- California Spring Break Vacation
- Bora Bora Honeymoon
- Romantic Getaways in Ohio
- Myrtle Beach Spring Break Hotels & Vacation Rentals
- Road Trips in Texas
Explore More Vacation Ideas
Hotels in Charleston, South Carolina
Hotels in Miami Beach
Beach Vacations in Pennsylvania
Pet Friendly Rentals in New Hampshire
Orlando Hotels & Vacation Rentals for Thanksgiving
Romantic Getaways in New Jersey
Must-See Events in New York
Road Trips in Maine
Pet Friendly Rentals at Clearwater Beach
Lake Vacations in New York
Romantic Getaway in Oregon
Dog Friendly Vacations in New England
Family Winter Getaways in New England
California Christmas Vacation
Plan your Family Spring Break in Florida
Orlando Hotels & Vacation Rentals for New Year's Eve
Ranch Vacation in Texas
Spring Break in Seattle
Hotels in Ocean City, Maryland
Family Vacation in San Francisco
Honeymoon in Georgia