Woodstock Vacation Packages

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Your Woodstock Vacation

Book a tailored Woodstock vacation package that includes only the things you need and nothing you don't. Great for families, festivals and markets, think about basing yourself in the neighborhood of Kingston Stockade District. If a sightseeing tour is part of the program during your trip to Woodstock, visit big attractions like Overlook Mountain Trailhead, Bethel Woods Museum and Opus 40. Don't put off visiting this destination any longer. The perfect Woodstock vacation is a couple of clicks away with Expedia.

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Woodstock Hotel Deals

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
10 Waterfall Way, Woodstock, NY
The price is CA $329 per night from Jul 30 to Jul 31
CA $329
CA $422 total
Jul 30 - Jul 31
includes taxes & fees
9.4/10 Exceptional! (160 reviews)
"Stunning room. Great amenities including a very cool turntable with a choice of albums from the 60s. Really nice balcony too."

Reviewed on Jun. 29, 2025

Woodstock Way Hotel
Hotel Dylan

Hotel Dylan

2 out of 5
320 Maverick Rd, Woodstock, NY
The price is CA $267 per night from Jul 30 to Jul 31
CA $267
CA $300 total
Jul 30 - Jul 31
includes taxes & fees
9.2/10 Wonderful! (25 reviews)
"The hotel was impeccably clean, such nice decor, office was cute. Pool amazing. There were games for all to enjoy, putting, cornhole table tennis. We would definitely go there again."

Reviewed on Jul. 18, 2025

Hotel Dylan
The Herwood Inn

The Herwood Inn

4.5 out of 5
148 Tinker St, Woodstock, NY
The price is CA $345 per night from Aug 12 to Aug 13
CA $345
CA $386 total
Aug 12 - Aug 13
includes taxes & fees
9.6/10 Exceptional! (80 reviews)
"Super cozy, quirky, with loving personal touches! Traffic on the road in front is a bit annoying but we love this place and will be back again and again!"

Reviewed on Jul. 23, 2025

The Herwood Inn
See all 2,412 properties in Woodstock
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.
All Inclusive Vacations
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Discover the most popular places to visit in Woodstock

Karma Triyana Dharmachakra Monastery

Learn about the local history of Woodstock with a stop at Karma Triyana Dharmachakra Monastery. Discover the mountain views while you're in the area.

Karma Triyana Dharmachakra Monastery

Woodstock Public Library

Woodstock Public Library is just one of the places to see in Woodstock, so why not enjoy the other things to explore during your travels? Discover the mountain views while you're in the area.

Woodstock Public Library

Frequently asked questions

How much does a Woodstock vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Woodstock costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Woodstock?
You can generally find reduced prices and better availability in January, May and November. Take a look at our cheap Woodstock vacation packages and you could score some great off-season deals.
How many days is enough for Woodstock?
Woodstock vacations come in all shapes and sizes, but to get a true feel for this place, we think 2 days is about right. This will mean you can visit major attractions like Opus 40 and Karma Triyana Dharmachakra Monastery and track down some hidden gems. Don't forget to visit cool neighbourhoods such as Bearsville and Zena either. If you're clever with your time, you may even be able to take a day trip or two from Woodstock too.
Is it worth booking a vacation package to Woodstock?
Whether you'd like to explore major attractions like Overlook Mountain Trailhead and Karma Triyana Dharmachakra Monastery on your Woodstock vacation, or coming for its great markets, hiking and cycling, there's something for everyone here. With so much to do, you'll soon find out why so many people think Woodstock is a good vacation destination.
How to find the best Woodstock package deals?
Begin your search for a Woodstock package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Woodstock package deal right away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Woodstock adventure off to a flying start.
Is it cheaper to book a Woodstock vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still get the freedom to create a personalized Woodstock vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Woodstock?
Land incredible bargains by reserving your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Woodstock escape.
How to plan a trip to Woodstock?

  1. Choose when to travel: Check your calendar and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to visit Woodstock.
  2. Budget wisely: As well as the price of your accommodations, you should consider other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that may crop up during your trip to Woodstock.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you want to get to in Woodstock. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your accommodations and airfare: Once you've nailed down your dates and duration, book the ideal 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.