Woodstock Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.

Ready to book your vacation to Woodstock?

Choose your dates

Woodstock Hotel Deals

Woodstock Way Hotel

Woodstock Way Hotel

10 Waterfall Way Woodstock NY
CA $420
CA $525 total
Sep 7 - Sep 8
includes taxes & fees
9.6/10 Exceptional! (302 reviews)
"This hotel was in a perfect location to all shops and restaurants. The area was peaceful and staff were great. The room was beautiful and clean. I would highly recommend!"

Reviewed on Aug 11, 2026

Woodstock Way Hotel
The Herwood Inn

The Herwood Inn

148 Tinker St Woodstock NY
CA $378
CA $424 total
Aug 17 - Aug 18
includes taxes & fees
9.6/10 Exceptional! (129 reviews)
"We stayed in dog friendly Mitchel Manor. The host was extremely helpful and accommodating. Room was clean and the shared patio was especially nice."

Reviewed on Aug 14, 2026

The Herwood Inn
Twin Gables of Woodstock

Twin Gables of Woodstock

73 Tinker St Woodstock NY
CA $263
CA $316 total
Sep 8 - Sep 9
includes taxes & fees
9.8/10 Exceptional! (221 reviews)
"Our stay at Twin Gables was lovely, right in the heart of Woodstock on Tinker St. We booked for a concert that was cancelled and decided to just make a getaway day of it. Immaculate room (#1 on main floor), very quiet. Good bed, a little firm than we're used to but comfy. Nice big bathroom, spacious ..."

Reviewed on Aug 12, 2026

Twin Gables of Woodstock
See all 2,485 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

Stay near popular Woodstock attractions

Woodstock Music Shop

9.6/10 (18 reviews)
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.
See properties

Overlook Mountain Trailhead

9.6/10 (34 reviews)
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.
See properties

Bearsville Theater

You can get tickets for a performance at Bearsville Theater on your trip to Woodstock. Amble around this relaxing area's forest or experience its art scene.
See properties

Colony

You can get tickets for a performance at Colony during your stay in Woodstock. Amble around this relaxing area's forest or experience its art scene.
See properties

Karma Triyana Dharmachakra Monastery

10.0/10 (12 reviews)
After visiting Karma Triyana Dharmachakra Monastery, make a plan to see the other sights and activities in Woodstock. Discover the mountain views while you're in the area.
See properties

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 forest or experience its art scene.
See properties

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 forest or experience its art scene.
See properties

Woodstock Artists Association and Museum

You can spend time browsing the exhibits at Woodstock Artists Association and Museum in Woodstock. Amble around this relaxing area's forest or experience its art scene.
See properties

Frequently asked questions

How much does a Woodstock vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Woodstock costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Woodstock?
You can generally find reduced prices and better availability in January, May and November. Take a look at our cheap Woodstock vacation packages and you could score some great off-season deals.
How many days is enough for Woodstock?
Woodstock vacations come in all shapes and sizes, but to get a true feel for this place, we think 2 days is about right. This will mean you can visit major attractions like Opus 40 and Karma Triyana Dharmachakra Monastery and track down some hidden gems. Don't forget to visit cool neighbourhoods such as Bearsville and Zena either. If you're clever with your time, you may even be able to take a day trip or two from Woodstock too.
Is it worth booking a vacation package to Woodstock?
Whether you'd like to explore major 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 much to do, you'll soon find out why so many people think Woodstock is a good vacation destination.
How to find the best Woodstock package deals?
Begin your search for a Woodstock package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Woodstock package deal right away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Woodstock adventure off to a flying start.
Is it cheaper to book a Woodstock vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still get the freedom to create a personalized Woodstock vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Woodstock?
Land incredible bargains by reserving your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Woodstock escape.
How to plan a trip to Woodstock?
  1. Choose when to travel: Check your calendar and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to visit Woodstock.
  2. Budget wisely: As well as the price of your accommodations, you should consider other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that may crop up during your trip to Woodstock.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you want to get to in Woodstock. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your accommodations and airfare: Once you've nailed down your dates and duration, book the ideal Woodstock vacation package for you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.