Woodstock Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Woodstock

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
10 Waterfall Way, Woodstock, NY
9.4/10 Exceptional! (168 reviews)
Highly recommend this tranquil gem
"I stayed here two years ago and have been hoping to be able to come back since then. The rooms are so beautiful and comfortable, the setting just gorgeous. Everything is a convenient walk away. Staff are laid back, friendly, and helpful."

Reviewed on 15 Aug 2025

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Woodstock Way Hotel
Hotel Dylan

Hotel Dylan

2 out of 5
320 Maverick Rd, Woodstock, NY
The price is 5.742.436 ₫ per night from 26 Aug to 27 Aug
5.742.436 ₫
6.431.812 ₫ total
26 Aug - 27 Aug
includes taxes & fees
9.2/10 Wonderful! (28 reviews)
"amazing place"

Reviewed on 31 Jul 2025

Hotel Dylan
The Herwood Inn

The Herwood Inn

4.5 out of 5
148 Tinker St, Woodstock, NY
The price is 6.874.271 ₫ per night from 16 Sept to 17 Sept
6.874.271 ₫
7.699.184 ₫ total
16 Sept - 17 Sept
includes taxes & fees
9.6/10 Exceptional! (82 reviews)
"We enjoyed the convenience and walkability. Downtown Woodstock is about a 10 to 15 minute easy walk to shops and eateries. We stayed in the King Suite, a 2nd floor lodging that was clean, spacious and included pretty much all you need for a stay (games, books, kitchenette, toaster oven, pots, pans, ..."

Reviewed on 7 Aug 2025

The Herwood Inn
See all 2,417 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.

Popular places to visit

Overlook Mountain Trailhead

Learn about the local history of Woodstock when you take a trip to Overlook Mountain Trailhead. Discover the mountain views while you're in the area.

Overlook Mountain Trailhead

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

Byrdcliffe Barn

Byrdcliffe Barn 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

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.