0 Bedrooms for 1 Guest
Price $10 - $1000+

431 Woodstock Holiday Rentals, Houses & Apartments

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Woodstock holiday rentals from 7 rental sites including HomeAway, TripAdvisor, Booking.com, and more, ranging from $47 to $1800 a night. 
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    Information about Woodstock

    About Woodstock

    A mecca for artists in the woods of New York, Woodstock has a long history of attracting painters, musicians, and festivalgoers. It was established in 1787 by European settlers and began industrializing in the early 1800s. Though Woodstock’s reputation is preceded by the infamous festival of the same name, it actually isn’t hosted in the town. The permit for the festival was turned down in Woodstock, so it moved 60 miles away a dairy farm in Bethel. Woodstock, dubbed “the most famous small town in the world,” remains tied to its history and aims to keep the past alive in its art and preservation of natural beauty.

    Things to do in Woodstock

    Woodstock is full of eclectic shops that are sure to interest travelers. Shop for jewelry, handmade ceramic pieces, or even Tibetan décor. In the warmer months, be sure to stop by Mower’s Saturday Market for antiques, produce, and other unique gifts from local vendors.

    Whether you’re a foodie or you just enjoy a good meal, Woodstock has many fine restaurants that often offer organically sourced food and diverse menus. Try top-rated Provisions deli for a pastrami sandwich or vegan dessert. For a laid-back drink, check out The Commune Saloon, featuring a fire pit and live music.

    Enjoy the benefits of Woodstock’s healing community by checking out their spas and holistic studios. Visit The Emerson Spa for a relaxing massage, or check out Mountain View Studio for an interdisciplinary healing experience.

    Each summer, Woodstock hosts a summer concert series called Concerts on the Green, which are free concerts suitable for all ages. There is also Jazzstock, which celebrates jazz music year round. Summer visitors can also check out Maverick Concerts, the award-winning chamber music festival at a unique venue in the woods.

    Day Trips from Woodstock

    Nature enthusiasts will find plenty of hiking, fishing, and camping at Big Indian Wilderness. You will find the longest stretch of trail through pristine forest in the Catskill Mountains. Try the Mongaup-Hardenburg Trail for a moderately difficult hike offering opportunities for birdwatching and other animal life.

    Take a one-hour drive North to Albany, which is New York’s capital. Take a free tour of the capitol building, stroll through Washington Park, and stop for dinner at top-rated Athos Restaurant.

    History enthusiasts can’t miss a tour of Franklin Delano Roosevelt’s home. Only a 45-minute drive from Woodstock, this historic site contains the former president’s home, the Eleanor Roosevelt National Historic Site, and the Vanderbilt Mansion National Historic Site. The grounds are free to visitors, but tours start at $10 per person.

    Woodstock Accommodations

    A quick search on Tripping.com yields nearly 200 results for vacation rentals. Pick a spot in the woods for a secluded vacation or a spot close to the Hudson River for quick access to kayaking and canoeing. Many rentals are quaint cottages and cabins, perfect for your relaxing vacation to Woodstock.

    Transportation in Woodstock

    Woodstock can be reached from the East and West through New York State Route 212. Within Woodstock, there are many taxi services as well as bus service through Adirondack Pine Hill Trailways. There are also many walking trails within the town. The nearest major airport is Stewart International Airport, 48 miles away from Woodstock.

    Vacation Rentals in Woodstock

    Save hundreds with a Tripping.com vacation rental and forget about the expensive hotel room. For the ultimate getaway trip, Woodstock offers 430 vacation home rentals for an affordable price to match your budget and accommodation needs. Book one now for an average price of $293 a night, or a long-term rental for an average price of $6317 a month.

    These homes offer a range of amenities, giving you more bang for your buck. For those looking to stay in a corporate rental, 322 of Woodstock’s rentals offer high speed internet so you can easily keep in touch with your company or team. Go for a swim at one of the 91 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 347 cozy homes.

    Traveling with pets? Choose from 201 pet-friendly rentals in Woodstock for a quality experience. Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your furry buddy. Book instantly with properties marked “Instabook”, and check out our other listings now to find the perfect vacation home for you.

    Search properties from 7 rental sites in Woodstock where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 284 HomeAway rentals, 74 TripAdvisor short term rentals and 50 Booking.com vacation rentals.