Woodstock Vacations

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Your Woodstock Vacation

Book a tailored Woodstock vacation 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 neighborhood of Kingston Stockade District. If a sightseeing tour is part of the program 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 vacation is a couple of clicks away with Expedia.

Discover the most popular places to visit in Woodstock

Manufacture of guitars of the brand Woodstock.

Woodstock Music Shop

You can search for that perfect souvenir at Woodstock Music Shop during your trip to Woodstock. Discover the mountain views while you're in the area.

Woodstock Music Shop

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

Woodstock Hotel Deals

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
10 Waterfall Way Woodstock NY
$277 nightly
The price is $305 total per night from Feb 2 to Feb 3
$305 total
Feb 2 - Feb 3
Total with taxes and fees
9.4/10 Exceptional! (229 reviews)
Wonderful place to stay! Beautiful, clean, spacious! Wished we could have stayed longer!

Reviewed on Jan 31, 2026

Woodstock Way Hotel
The Herwood Inn

The Herwood Inn

4.5 out of 5
148 Tinker St Woodstock NY
$114 nightly
The price is $128 total per night from Feb 3 to Feb 4
$128 total
Feb 3 - Feb 4
Total with taxes and fees
9.6/10 Exceptional! (97 reviews)
The hot tub was, by far, one of the nicest we have had at an inn. The cedar smelled delicious and was perfect after a long day of skiing.

Reviewed on Jan 22, 2026

The Herwood Inn
Twin Gables of Woodstock

Twin Gables of Woodstock

3 out of 5
73 Tinker St Woodstock NY
$139 nightly
The price is $156 total per night from Feb 2 to Feb 3
$156 total
Feb 2 - Feb 3
Total with taxes and fees
9.6/10 Exceptional! (196 reviews)
We had the best stay just a couple of weeks ago at the start of January. The space itself is clean & has funky decor, and each room definitely has its own theme/vibe, which is nice and separates itself from a sterile hotel room. Good restaurants & boutique shopping within walking distance, and easy ...

Reviewed on Jan 20, 2026

Twin Gables of Woodstock
See all 2,449 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.

Find the Best Woodstock Vacation Packages

Things to do in and around Woodstock

Woodstock, New York, offers a fantastic blend of outdoor adventures and scenic beauty. Visitors can enjoy skiing at local ski resorts and explore the picturesque landscapes. For those seeking more excitement, an activity guide is available, along with options for golf and adventures along Tinker Street, where you can find charming shops and eateries. Whether you're hitting the slopes or exploring the vibrant local scene, Woodstock promises a memorable vacation experience.

Shopping

In Woodstock, visit the Woodstock Music Shop for unique gifts and souvenirs. If you're up for a drive, check out Hudson Valley Mall and Vinnie's Farm Market, both 9 miles away, offering a variety of shopping experiences amidst vibrant city vibes.

Recreation

Relax at Saugerties Village Beach, a serene spot perfect for unwinding and enjoying nature just 9 miles from Woodstock. For a cultural experience, visit the Ulster Performing Arts Center, offering entertainment and romance 10 miles away. For sports enthusiasts, Dietz Stadium, located 9 miles away, provides thrilling athletic events.

Adventure

Experience the thrill of skiing at Hunter Mountain, located 12 miles from Woodstock, offering exhilarating slopes for all skill levels. For hiking enthusiasts, the Overlook Mountain Trailhead provides stunning outdoor scenery right in Woodstock. Enjoy family adventures at North-South Lake Campground, also 12 miles away, perfect for outdoor fun.

Nightlife

Woodstock's nightlife is a blend of cozy bars and vibrant music venues. Visit The Bearsville Theater for live performances, or unwind at The Woodstock Brewing Company for local craft beers. For a laid-back vibe, explore the intimate atmosphere at The Tinker Street Tavern with great food and drinks.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Woodstock

Woodstock, New York, is a perfect destination for outdoor enthusiasts and adventure seekers, offering stunning scenery and a rich cultural experience. Visitors can explore a variety of points of interest, including beautiful nature preserves, picturesque waterfalls, and historic college campuses. Whether you're looking for family-friendly activities or a taste of local culture, Woodstock has something to offer every traveler.

  • Bethel Woods Museum: Located just 3 miles from Woodstock, this museum celebrates the rich cultural history of the 1969 Woodstock Festival. Explore engaging exhibits and enjoy the beautiful grounds that host concerts and events throughout the year, making it a vibrant hub for music lovers and history buffs alike.
  • Kaaterskill Falls: About 11 miles away, Kaaterskill Falls is a stunning two-tiered waterfall that offers breathtaking views and adventure. Hike the scenic trails, perfect for couples and outdoor enthusiasts, and immerse yourself in the natural beauty of the Catskills.
  • Bard College: This historic college, also 11 miles from Woodstock, boasts stunning architecture and picturesque grounds. Visit its galleries and attend performances, experiencing a blend of education and culture in a beautiful setting.

Best time to go to Woodstock

The best time to visit Woodstock can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Woodstock falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Woodstock falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.0°F (-3.9°C)Light RainMostly SunnySlightly LowSlightly Low
February26.6°F (-3.0°C)Light RainMostly CloudyAverageAverage
March34.5°F (1.4°C)Light RainMostly SunnyAverageSlightly Low
April46.2°F (7.9°C)Light RainMostly SunnyAverageSlightly Low
May57.7°F (14.3°C)Light RainMostly SunnyAverageAverage
June65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
July71.6°F (22.0°C)Light RainMostly SunnySlightly HighSlightly High
August69.6°F (20.9°C)Light RainMostly SunnySlightly HighSlightly High
September62.6°F (17.0°C)Light RainMostly SunnySlightly HighAverage
October51.4°F (10.8°C)Light RainMostly SunnyAverageSlightly High
November39.0°F (3.9°C)Light RainMostly SunnySlightly LowAverage
December31.1°F (-0.5°C)Light RainMostly CloudySlightly LowAverage

Tips to save on your trip to Woodstock

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Woodstock.
  • Consider traveling during the off-peak season (typically January and March to April) for more affordable package holidays to Woodstock.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Woodstock Essential Information

Language
English
Currency
U.S dollars
Population
2,100
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Ulster Performing Arts Center, Kingston Point Beach and Mount Tremper Arts

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Frequently asked questions

How much does a Woodstock vacation package cost?
You can snap up a vacation package to this destination on Expedia. But how much your vacation 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?
If you're hoping to book a cheap Woodstock vacation package, consider planning a trip in May, October and November. You'll typically find lower prices on airfares and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Woodstock?
With about 2 days, you'll have enough time to experience popular neighborhoods like Zena and West Hurley during your Woodstock vacation. Remember to also add Woodstock Golf Club and Thorn Preserve - Catskill Center to your sightseeing list. Searching for more adventures? Consider venturing outside of Woodstock on day trips and tours.
Is it worth booking a vacation package to Woodstock?
Whether you'd like to explore key attractions like Overlook Mountain Trailhead and Karma Triyana Dharmachakra Monastery on your Woodstock vacation, or coming for its great markets, hiking and cycling, there's something for everyone here. With so many things to see and do, you'll soon learn why so many people think Woodstock is a good vacation destination.
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 customize your search by "Property class," "Number of bedrooms," "Traveler 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 vacation as a package?
Expedia vacation 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 customized Woodstock vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Woodstock?
If you have your Woodstock vacation 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 go: Check your calendar and get your bags packed. Your favorite time of year and the activities on offer will also help you decide when to escape to Woodstock.
  2. Set a budget: Factor in costs like food, flights and transportation when calculating how much to save for your trip to Woodstock. Then, choose a property that fits your budget, whether that's an affordable stay or a deluxe getaway.
  3. Discover Woodstock using our trip planning tool: Gain insights into the top attractions and best stays for your trip to Woodstock. You can also save your favorite locations, collaborate with family and friends and organize all your plans in one place.
  4. Set the duration of your trip: Start by listing all the activities and sights you'd like to get to in Woodstock. Then, estimate how long you'll need at each, including any travel time.
  5. Combine your accommodations and airfare: After you've settled on your dates and duration, lock in the ideal Woodstock vacation package for you.
  6. Add on excursions and experiences: Have a look at our dedicated travel guide to find some awesome things to do in Woodstock. Book tickets or make reservations before you go to save time and avoid the stress of looking for activities when you arrive.

Does Expedia offer Book Now, Pay Later Woodstock vacation packages?
Secure your dream trip to Woodstock with our Book Now, Pay Later vacations. There's no need to save up or wait for your next payday — we've teamed up with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snap up bargains before they sell out.

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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.