Woodstock Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Woodstock

Woodstock Way Hotel
Woodstock Way Hotel
4 out of 5
10 Waterfall Way, Woodstock, NY
The price is S$452 per night from 24 Feb to 25 Feb
S$452
includes taxes & fees
24 Feb - 25 Feb
9.4/10 Exceptional! (140 reviews)
"Really cute tucked away area and also incredibly close to the town of Woodstock with all of its shops and restaurants so you don't need to drive once you're here. I loved the simple design of the rooms as well as their pet friendly options and small coffee shop that has a full coffee bar and snacks ..."

Reviewed on 26 Jan,2025

Woodstock Way Hotel
The Herwood Inn
The Herwood Inn
4.5 out of 5
148 Tinker St, Woodstock, NY
The price is S$267 per night from 5 Mar to 6 Mar
S$267
includes taxes & fees
5 Mar - 6 Mar
9.8/10 Exceptional! (56 reviews)
"Great customer service and location"

Reviewed on 3 Feb,2025

The Herwood Inn
Twin Gables of Woodstock
Twin Gables of Woodstock
2.5 out of 5
73 Tinker St, Woodstock, NY
The price is S$224 per night from 23 Feb to 24 Feb
S$224
includes taxes & fees
23 Feb - 24 Feb
9.6/10 Exceptional! (139 reviews)
"Great room in a charming property"

Reviewed on 10 Feb,2025

Twin Gables of Woodstock
See all 2,287 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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.