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157 Woodstock Holiday Rentals

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Compare Woodstock holiday rentals from 5 rental sites including HomeAway, TripAdvisor, Booking.com and more, from $59 a night.

Woodstock Information

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 vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Woodstock offers 154 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Woodstock start at an average price of $306 a night with long-term rentals averaging $25 a month.

These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 138 of Woodstock’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 42 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 132 vacation home rentals.

Traveling with your dog or cat? Choose from 76 pet-friendly rentals in Woodstock that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go!

Search properties from 5 vacation rental sites in Woodstock where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 123 HomeAway rentals, 21 TripAdvisor short term rentals and 7 Booking.com vacation rentals.