Woodstock Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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
9.4/10 Exceptional! (159 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
The price is S$285 per night from 17 Jul to 18 Jul
S$285
17 Jul - 18 Jul
includes taxes & fees
9.4/10 Exceptional! (23 reviews)
"Amazing stay with hotel Dylan, wonderful space and friendly staff"

Reviewed on 19 Jun, 2025

Hotel Dylan
Morning Glory B n B Woodstock NY
Morning Glory B n B Woodstock NY
3 out of 5
141 Tinker Street, Woodstock, NY
The price is S$285 per night from 21 Jul to 22 Jul
S$285
21 Jul - 22 Jul
includes taxes & fees
8.8/10 Excellent! (115 reviews)
Beautiful historic home
"Beautiful historic home. We had a nice stay."

Reviewed on 24 Jun, 2025

Morning Glory B n B Woodstock NY
See all 2,414 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

Rip van Winkle II passing the Rondout Lighthouse

Hudson River Sightseeing Cruise from Kingston

S$54
per adult
84% of travellers recommend
Hudson River Sightseeing Cruise from Kingston
Self-Guided Audio Driving Tour in Catskills Scenic Byway

Self-Guided Audio Driving Tour in Catskills Scenic Byway

S$22
per traveller
Self-Guided Audio Driving Tour in Catskills Scenic Byway
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. 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.