Woodstock Holidays

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Woodstock Holiday

Our pick of the best Woodstock Hotel Deals

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
10 Waterfall Way, Woodstock, NY
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 29 Jun. 2025

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Woodstock Way Hotel
Hotel Dylan

Hotel Dylan

2 out of 5
320 Maverick Rd, Woodstock, NY
Fully refundableReserve now, pay when you stay
The price is NZ$365 per night from 28 July to 29 July
NZ$365
28 July - 29 July
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 18 Jul. 2025

Hotel Dylan
The Herwood Inn

The Herwood Inn

4.5 out of 5
148 Tinker St, Woodstock, NY
The price is NZ$471 per night from 4 Aug to 5 Aug
NZ$471
4 Aug - 5 Aug
includes taxes & fees
9.6/10 Exceptional! (79 reviews)
"Everything about our stay was amazing. Our room Nick’s Nook was adorable and had great amenities and a cool vibe. We did not use the back space (pergola and hot tub) but everything looked so nice and relaxing! Thank you!!!"

Reviewed on 16 Jul. 2025

The Herwood Inn
See all 2,410 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.

What to do in Woodstock

Self-Guided Audio Driving Tour in Catskills Scenic Byway

Self-Guided Audio Driving Tour in Catskills Scenic Byway

NZ$28
per traveller
Self-Guided Audio Driving Tour in Catskills Scenic Byway
We have 50 animals here at Napping House Farm. These include horses, donkeys, chickens, pigs, geese, emus, and goats!

Meet Our Rescue Animals: Private Tour of A Family-Run Farm

NZ$162
per traveller
100% of travellers recommend
Meet Our Rescue Animals: Private Tour of A Family-Run Farm
See all activities in Woodstock

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.