Woodstock Vacations
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Find the Best Woodstock Vacation Packages
Woodstock Hotel Deals
Woodstock Way Hotel
10 Waterfall Way Woodstock NY
₩424,554
₩530,407 total
Aug 25 - Aug 26
includes taxes & fees
9.6/10 Exceptional! (300 reviews)
"Absolutely perfect little oasis right in the middle of town. It’s amazing that it can feel so serene and beautiful and be around the corner from the Main Street. We meditated every morning on our private balcony overlooking the stream. I highly recommend it!"
Reviewed on Aug 7, 2026
Twin Gables of Woodstock
73 Tinker St Woodstock NY
₩266,086
₩319,303 total
Sep 8 - Sep 9
includes taxes & fees
9.8/10 Exceptional! (220 reviews)
"LeAnn was very helpful. She gave great guidance about hiking and music."
Reviewed on Jul 27, 2026
The Herwood Inn
148 Tinker St Woodstock NY
₩383,147
₩429,116 total
Sep 2 - Sep 3
includes taxes & fees
9.6/10 Exceptional! (128 reviews)
"Great location and property. Wonderful host. Room had terrific on theme touches."
Reviewed on Jul 26, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Woodstock attractions
Woodstock Music Shop
9.6/10 (18 reviews)
Vinyl paradise awaits at Woodstock Music Shop with its curated collection spanning countless genres. Engage with knowledgeable staff who can guide you to musical treasures among the rare albums and handcrafted vinyl art.
Overlook Mountain Trailhead
9.6/10 (34 reviews)
Hike through ruins of the historic Overlook Mountain House before reaching a restored fire tower. Climb to the summit for breathtaking 360-degree views of the Hudson Valley and Catskill Mountains.
Bearsville Theater
You can get tickets for a performance at Bearsville Theater on your trip to Woodstock. Amble around this relaxing area's forest or experience its art scene.
Karma Triyana Dharmachakra Monastery
10.0/10 (12 reviews)
This Tibetan Buddhist monastery showcases a magnificent two-story Buddha statue and serves as the Gyalwang Karmapa's North American seat. Join free weekend guided tours to learn about sacred traditions.
Colony
This historic Woodstock venue blends rustic charm with live music in an intimate setting. Enjoy performances in the vintage ballroom or unwind in the beer garden with dinner and craft cocktails.
Tinker Street Tavern
Tinker Street Tavern is just one of the places to see in Woodstock, so why not enjoy the other things to explore during your travels? Amble around this relaxing area's forest or experience its art scene.
Byrdcliffe Barn
This historic barn at Byrdcliffe Arts Colony preserves Woodstock's artistic heritage in a rustic setting. Attend evening concerts or exhibitions between May and October for an authentic cultural experience.
Woodstock Artists Association and Museum
Founded in 1919, this cultural cornerstone showcases Woodstock's artistic heritage through diverse exhibitions. Explore intimate galleries of local art in this free museum where art history comes alive.
Frequently asked questions
How much does a Woodstock vacation package cost?
You can snap up a vacation package to this destination on Expedia. But how much your vacation to Woodstock costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Woodstock?
January, May and November are the best times to search for cheap Woodstock vacation packages. Choosing to travel in less busy periods means you can usually find better prices on accommodations and flights.
How many days is enough for Woodstock?
To fully enjoy a Woodstock vacation, we recommend staying for 2 days. Divide your time between visiting Woodstock Golf Club, Thorn Preserve - Catskill Center and other must-see attractions, as well as experiencing neighborhoods like Bearsville and Zena. If you've got some spare time, add a tour or day trip to your Woodstock vacation itinerary.
Is it worth booking a vacation package to Woodstock?
Popular for its markets, hiking and cycling, a Woodstock vacation has something for everyone. Be sure to check out top sights like Overlook Mountain Trailhead and Karma Triyana Dharmachakra Monastery, and consider renting a car for day trips to discover even more.
How to find the best Woodstock package deals?
Bagging a cheap Woodstock package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add some filters and browse what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Woodstock package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Woodstock vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Woodstock vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Woodstock?
If you have your Woodstock vacation dates confirmed, book early to grab some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Woodstock?
- Choose when to travel: Check your schedule and pack your bags. Your preferred time of year and the activities available will also help you decide when to vacation in Woodstock.
- Set your budget: Consider expenses like flights, transportation and food when calculating how much to put aside for your trip to Woodstock. Then, select a property that suits your budget, whether that's a low-cost option or a more luxurious getaway.
- Decide how long to go away for: Now that you know more about Woodstock, you can work out the right length of your break. Pull together a rough itinerary and give yourself enough time to get through everything on your must-do list.
- Bundle your accommodations and airfare: Once you've nailed down your trip dates and duration, lock in the perfect Woodstock vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
