Woodstock Holidays

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Your Woodstock Holiday

Book a tailored Woodstock holiday 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 neighbourhood of Kingston Stockade District. If a sightseeing tour is part of the programme 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 holiday is a couple of clicks away with Expedia.

Woodstock Essential Information

Language
English
Currency
U.S dollars
Population
2,100
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Hunter Mountain, Kaaterskill Falls and Ulster Performing Arts Centre

Top hotels in Woodstock

Woodstock Way Hotel

Woodstock Way Hotel

10 Waterfall Way Woodstock NY
£300
17 Sept - 18 Sept
includes taxes & fees
9.6/10 Exceptional! (308 reviews)
"Loved the fire pits and right in town."

Reviewed on 12 Sept 2026

Woodstock Way Hotel
Twin Gables of Woodstock

Twin Gables of Woodstock

73 Tinker St Woodstock NY
£177
23 Sept - 24 Sept
includes taxes & fees
9.8/10 Exceptional! (225 reviews)
"Lovely property and very well maintained interior. Great location in the center of town. I’d create more parking out back (especially since the presence of deer poop all over the grass did not make for a good outdoor space to hang in). Loved morning yoga on the rooftop! Would’ve enjoyed coffee up ..."

Reviewed on 3 Sept 2026

Twin Gables of Woodstock
The Herwood Inn

The Herwood Inn

148 Tinker St Woodstock NY
£165
22 Sept - 23 Sept
includes taxes & fees
9.6/10 Exceptional! (135 reviews)
"Good location, walkable to the shops and dining options nearby. Owners were communicative (if necessary). Could tell that they took pride the property, the vegetation was lush and beautiful. One unexpected amenity - a drawer dishwasher."

Reviewed on 15 Sept 2026

The Herwood Inn
See all 2,474 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.
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Stay near popular Woodstock attractions

Woodstock Music Shop

9.6/10 (18 reviews)
Vinyl paradise awaits at Woodstock Music Shop with its curated collection spanning countless genres. Engage with knowledgeable staff who can guide you to musical treasures among the rare albums and handcrafted vinyl art.
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Overlook Mountain Trailhead

9.6/10 (34 reviews)
Hike through ruins of the historic Overlook Mountain House before reaching a restored fire tower. Climb to the summit for breathtaking 360-degree views of the Hudson Valley and Catskill Mountains.
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Colony

This historic Woodstock venue blends rustic charm with live music in an intimate setting. Enjoy performances in the vintage ballroom or unwind in the beer garden with dinner and craft cocktails.
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Bearsville Theater

You can get tickets for a performance at Bearsville Theater during your trip to Woodstock. Amble around this relaxing area's forests or experience its art scene.
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Karma Triyana Dharmachakra Monastery

10.0/10 (12 reviews)
This Tibetan Buddhist monastery showcases a magnificent two-story Buddha statue and serves as the Gyalwang Karmapa's North American seat. Join free weekend guided tours to learn about sacred traditions.
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Woodstock Public Library

8.8/10 (25 reviews)
The historic Woodstock Public Library District has served as a community learning hub since 1913. Currently closed for relocation until 2025, visitors should check their website for pop-up events and digital services.
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Tinker Street Tavern

Tinker Street Tavern 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.
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The Comeau Property

This serene park offers peaceful trails through forests and along the Saw Kill stream, near city centre Woodstock. Explore meadows and woodlands while enjoying this tranquil natural escape.
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Frequently asked questions

Why should I book my Woodstock holiday with Expedia?
Expedia has you covered for all aspects of your Woodstock getaway. You'll always land the best deal possible, but when you bundle your accommodation, airfares and/or hire car into a holiday package, you'll score even bigger savings. Looking to really make the most of your stay? Add a few exciting tours and activities to your package. Expedia offers flexible cancellation policies on most bookings, so you won't need to stress if your plans change. Head over to our Customer Service Portal link to discover more.
When is the best time of year to holiday in Woodstock?
Woodstock is a busy place in March, April and June. If you don't like crowds and prefer a quieter pace, book your escape for May, October and November. To get an idea of the type of weather you can experience, the average temperature during the day in January, the coolest time of year in Woodstock, is -4ºC. The warmest period here is July, when temperatures reach an average of 22ºC.
What are the top hotels for my holiday in Woodstock?
One of the favourite places to stay in Woodstock is The Lodge Woodstock, in the Zena area. Wander the city by day and then kick back in this home away from home at night.
How do I get a cheap holiday to Woodstock?
Lock in flights that fit your busy schedule, add a hotel to your booking and see how much you save with a Woodstock holiday. It's as simple as that! From flights and hotels to tours and hire cars, Expedia makes travelling cheaply a cinch. And with more than 400 airlines and 321,000 hotels around the globe to select from, you won't be short of choice. Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Woodstock holiday?
Make sure your holiday in Woodstock is an unforgettable one by exploring its leading attractions. Overlook Mountain Trailhead, Indian Head Mountain, Karma Triyana Dharmachakra Monastery and Woodstock Music Shop are just a few of the things you should see while you're in the area.
What is the best area to stay in when on holiday in Woodstock?
Woodstock has plenty of wonderful places to discover, including Overlook Mountain Trailhead. Stay someplace near this attraction and make sightseeing a breeze.
Do I need a visa for my Woodstock holiday?
Official government websites will have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and reason for visiting, whether it be for tourism or business, will determine if you need a visa for Woodstock. Also double-check that your passport is up to date and has at least six months validity remaining beyond your planned date of return. Finalise all your travel planning well in advance to avoid any nasty last-minute surprises.
What should I wear on my Woodstock holiday?
First, consider the types of activities you'll be doing during your Woodstock holiday and take versatile pieces that you can mix and match. For fashion inspiration or even information on dress codes, browse style blogs or social media accounts. Pack your bags with confidence by monitoring the forecast in Woodstock. July brings the warmest temperatures, with daily averages of 22ºC, while January days average -4ºC, making it the coolest month.
What does an Expedia Woodstock holiday include?
Flights, car hires and hotels, or any combination of them — it's your choice. Whether you're visiting Woodstock on a family road trip or adventuring with your friends, there's a bundle to suit your budget and style. Once you've made your booking, why not add on some tours and experiences? Expedia features all sorts of properties, with the most sought after in Woodstock including private holiday homes and apartments. With Expedia, you'll always enjoy the flexibility and freedom to customise your holiday any way you like.
Does Expedia offer Book Now, Pay Later Woodstock holidays?
Your bank balance shouldn't get in the way of going on holiday, so Expedia has come up with a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book your dream getaway without using up all your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your trip. Check out these flexible payment options:
  • Pay monthly holidays: If paying bite-sized amounts each month is what works best for you, Klarna can help. Paying in several transactions will make that dream getaway possible.
  • No-deposit holidays: Clicking on the "book now" button is much easier with this option. With no upfront fee for your escape, you can Book Now, Pay Later and start working on your travel itinerary.
Can I choose my airline with a Woodstock Expedia holiday?
You can, and with over 400 airlines to choose from globally, it's all about choice. Search the available options and find out which airline best suits your budget and needs.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.