Woodstock Holidays
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Woodstock Holiday
Our pick of the best Woodstock Hotel Deals
Woodstock Way Hotel
10 Waterfall Way Woodstock NY
NZ$710
3 Nov - 4 Nov
includes taxes & fees
Twin Gables of Woodstock
73 Tinker St Woodstock NY
NZ$266
17 Nov - 18 Nov
includes taxes & fees
9.8/10 Exceptional! (230 reviews)
"This a beautiful bed and breakfast! The rules were a little confusing at times, but overall the staff was flexible and helpful. Thank you for a good weekend!"
Reviewed on 18 Oct 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.
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.
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.
Woodstock Public Library
8.8/10 (25 reviews)
The historic Woodstock Public Library District has served as a community learning hub since 1913. Currently closed for relocation until 2025, visitors should check their website for pop-up events and digital services.
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.
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.
What to do in Woodstock
Self-Guided Audio Driving Tour in Catskills Scenic Byway
NZ$35
per traveller
Hudson Valley: Mindful Art and Photography Walk
NZ$582
per adult
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.
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- Mohonk Preserve Visitor Center
- Opus 40
- Museum of Rhinebeck History
- Millbrook Holidays
- Millbrook Vineyards and Winery
- Sullivan County Dramatic Workshop - Rivoli Theatre
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- G. Steve Jordan Gallery
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- Mount Tremper Arts
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- Visit Rifton
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
