Woodstock Vacation Packages

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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.

Woodstock Hotel Deals

Woodstock Way Hotel
Woodstock Way Hotel
4 out of 5
10 Waterfall Way, Woodstock, NY
The price is CA $408 per night from Jun. 4 to Jun. 5
CA $408
CA $511 total
includes taxes & fees
Jun 4 - Jun 5
9.4/10 Exceptional! (89 reviews)
"An absolute pleasure. I wouldn’t stay over in Woodstock at any other lodging after finding this gem."

Reviewed on May 7, 2024

Woodstock Way Hotel
Streamside Cottage Walking Distance to Town of Woodstock
Streamside Cottage Walking Distance to Town of Woodstock
Woodstock
The price is CA $218 per night from May 28 to May 29
CA $218
CA $435 total
includes taxes & fees
May 28 - May 29
9.8/10 Exceptional! (168 reviews)
Perfect for relaxing getaway
"Spent two nights and wanted a place where we could easily bike into town and got exactly that! The sound of the creek outside was so relaxing, accommodations were clean and comfy. Definitely would return!"

Reviewed on May 20, 2024

Streamside Cottage Walking Distance to Town of Woodstock
The Herwood Inn
The Herwood Inn
4.5 out of 5
148 Tinker St, Woodstock, NY
The price is CA $300 per night from Jun. 6 to Jun. 7
CA $300
CA $337 total
includes taxes & fees
Jun 6 - Jun 7
9.6/10 Exceptional! (33 reviews)
Woodstock
"Everything was great. Anything you want is there. Books, Records, Ice, Coffee ☕."

Reviewed on May 11, 2024

The Herwood Inn
See all 2,330 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

Frequently asked questions

How much does a Woodstock vacation package cost?
Our Woodstock vacation packages, which start from as low as , are the easiest way to save big bucks. Select your preferred hotels, flights and rental car to create a customized itinerary.
How do I get a cheap travel package to Woodstock?
Lock in flights that fit in with your schedule, add a hotel room to your booking and watch how much you save with a Woodstock vacation package. It’s as simple as that! From hotels and flights to rental cars and tours, Expedia is your gateway to cheap travel. And with more than 550 air carriers and 1,000,000 hotel options all over the world to select from, you won’t be short of choice.
Where should I stay in Woodstock?
Stay close to the action. Many people favor hotels in the vicinity of popular attractions, such as Overlook Mountain Trailhead, Karma Triyana Dharmachakra Monastery and Woodstock Music Shop.
What are the top hotels in Woodstock?
Twin Gables of Woodstock will be a perfect base for your Woodstock adventures. Situated in Zena, it’s one of the area’s top hotels.
How far in advance should I book my Woodstock vacation?
Be rewarded with the biggest variety and the cheapest prices by booking your Woodstock adventure nice and early. Airlines typically publish flights around 12 months prior to departure, so reserve your spot as soon as you can. That being said, Expedia is committed to providing you with the best deals around, so it’s always a good time to book your dream vacation!
What does an Expedia Woodstock travel package include?
It all comes down to what type of trip you’re contemplating. Woodstock travel deals can include car rentals, hotels and flights. You can mix and match to create the bundle that suits your style and budget. You can also add on activities and experiences after you’ve booked to score even bigger discounts.
What should I know before booking a Woodstock travel package?
You can save a tidy sum by bundling your airfares, hotels and rental cars. Once you’ve created your package, you can add on things like activities or tours. Your next awesome adventure is only a couple of clicks away.
Can I choose my airline with a Woodstock Expedia vacation package?
Definitely. Expedia has more than 550 partner airlines to pick from around the globe. With so many choices, finding the ideal carrier to whisk you off to Woodstock shouldn’t be hard.
If I'm not able to travel, can I cancel my Woodstock vacation package?
You sure can, and we’ll help you every step of the way. You may be able to cancel or amend your Woodstock vacation package at no cost within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company if your booking is older than that. If your circumstances unexpectedly change, have a look at our Customer Service Portal for further information.

Discover the most popular places to visit in Woodstock

Image for Overlook Mountain Trailhead

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
Image for Karma Triyana Dharmachakra Monastery

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
Image for Woodstock Music Shop

Woodstock Music Shop

5/5(1 review)

Enjoy a stop at Woodstock Music Shop, an entertaining place to visit in Woodstock. Discover the mountain views while you're in the area.

Woodstock Music Shop

Other vacations you might like

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