Deals on vacations and trips to Woodstock

Save when you book Woodstock, VT package deals

Choose two or more items and save on your trip:

Woodstock flight + hotel vacation packages

Mountaineer Inn

Top Woodstock hotels deals

Don't see what you're looking for?
See all available properties in Woodstock
View all properties
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.

Popular places to visit

Frequently asked questions

How much are vacation packages to Woodstock?
Adventure awaits in Woodstock, with Travelocity vacation packages from as little as $442. In addition to flights and hotels, these terrific deals make it a breeze to explore all corners of the world.
How long should my Woodstock vacation be?
Generally, 2 nights is what many tourists book for their Woodstock trip. That’s a good starting point, but there’s loads more to discover if you give yourself a little longer.
Where can I get the best vacation package deals for Woodstock?
Snapping up the best package deal to Woodstock is a cinch with Travelocity. With access to 400 air carriers and 1,000,000 properties across the globe, you’re spoiled for choice when selecting your flights and hotels.
Why should I book my Woodstock vacation package via Travelocity?
From enticing destinations to one-of-a-kind experiences, we have everything you need to satisfy your travel desires. Our friendly 24/7 customer support will also ensure you’re taken care of while you’re on your getaway. And don’t worry if you spot a cheaper price on your booking, we’ll match it. That’s our Price Match Guarantee.
Can I save money on my Woodstock car rental if I bundle it with a hotel or flight?
Sure can — combine your flight, car and hotel into a Woodstock vacation package and you can save plenty. With so much to discover in the Woodstock area, that set of wheels will make exploring a joy. Once you’ve settled into the driver’s seat, hit the wide open road and find your way to Fenway Park, a well-known sight approximately 110 mi from Woodstock.
What is the best time of year to go to Woodstock?
If you really want to wander wisely, is one of the best times to do it. That’s when you’ll find hotel rates tumble. By way of comparison, prices are at their highest around . are the most popular times to stay in Woodstock, so brace for snaking lines at major attractions. Prefer to travel outside peak season? You’ll find thinner crowds in .
Which airport is best for Woodstock?
Lebanon Municipal Airport (LEB) is where many travelers land. You’ll find it 10 mi east from inner Woodstock. You can also check out the fares to Rutland Southern Vermont Regional Airport (RUT), which is 20 mi away from central Woodstock.
What is there to do in Woodstock?
There is a certain kind of magic as you wander through the streets of Woodstock. Suicide Six Ski Area and Woodstock Country Club are just a couple of highlights that make this city such a sought-after destination, so add them to your to-do list.
Where should I stay when visiting Woodstock?
The The Shire Woodstock is popular with many travelers. Book as soon as possible before it’s too late.
Can I go on vacation to Woodstock at this time?
Discover all the info you need to know about travel restrictions and quarantine policies before you fly to Woodstock. Our Covid-19 Travel Advisor is full of advice to help make your vacation as hassle-free as possible.