Woodstock Holidays
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Your Woodstock Holiday
When a city getaway is calling, answer it with a holiday package to Woodstock. The neighbourhood of Kingston Stockade District, which is great for families, festivals and markets, makes a terrific base for your adventures. Make your trip to Woodstock even more exciting by including some sightseeing. Overlook Mountain Trailhead, Bethel Woods Museum and Opus 40 are among the major attractions you'll want to explore. Whoever you're escaping with and whether your budget is big or small, your ultimate Woodstock holiday is only clicks away with Expedia.
Woodstock Holiday
Woodstock Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 2,100 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Hunter Mountain, Kaaterskill Falls and Ulster Performing Arts Centre |
Our pick of the best Woodstock Hotel Deals
Woodstock Way Hotel
10 Waterfall Way Woodstock NY
AU$500
16 Sept - 17 Sept
includes taxes & fees
9.6/10 Exceptional! (307 reviews)
"Was a beautiful space made it great for a parents getaway."
Reviewed on 30 Aug 2026
Twin Gables of Woodstock
73 Tinker St Woodstock NY
AU$367
23 Sept - 24 Sept
includes taxes & fees
9.8/10 Exceptional! (225 reviews)
"Lovely property and very well maintained interior. Great location in the center of town. I’d create more parking out back (especially since the presence of deer poop all over the grass did not make for a good outdoor space to hang in). Loved morning yoga on the rooftop! Would’ve enjoyed coffee up ..."
Reviewed on 3 Sept 2026
The Herwood Inn
148 Tinker St Woodstock NY
AU$373
23 Sept - 24 Sept
includes taxes & fees
9.6/10 Exceptional! (134 reviews)
"This inn is very special! It has a relaxing, quiet atmosphere! Wonderful backyard space with areas to sit & unwind along with the hot tub that my husband loved! Our suite was nicely decorated, comfortable bed, and lots of nice amenities! Special touch was the record player with plenty of vintage ..."
Reviewed on 6 Sept 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.
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.
Bearsville Theater
You can get tickets for a performance at Bearsville Theater during your trip to Woodstock. Amble around this relaxing area's forests 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.
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 forests 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 Golf Club
9.0/10 (2 reviews)
This historic nine-hole golf course designed by Tom Bendelow offers a serene challenge among mature trees. Members and their guests enjoy bent-grass fairways and comprehensive instruction from April through October.
Frequently asked questions
How much does a Woodstock holiday package cost?
You can snap up a holiday package to this destination on Expedia. But how much your holiday 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 holiday packages. Choosing to travel in less busy periods means you can usually find better prices on accommodation and flights.
How many days is enough for Woodstock?
To fully enjoy a Woodstock holiday, we recommend staying for 2 days. Divide your time between visiting Woodstock Golf Club, Thorn Preserve - Catskill Centre and other must-see attractions, as well as experiencing neighbourhoods like Bearsville and Zena. If you've got some spare time, add a tour or day trip to your Woodstock holiday itinerary.
Is it worth booking a holiday package to Woodstock?
Popular for its markets, hiking and cycling, a Woodstock holiday 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 customise your search by "Property class," "Number of bedrooms," "Traveller 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 holiday as a package?
Expedia holiday 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 customised Woodstock holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Woodstock?
If you have your Woodstock holiday 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 holiday 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 accommodation and airfare: Once you've nailed down your trip dates and duration, lock in the perfect Woodstock holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
