Woodstock Vacations

Book a Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to ₩234,741 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Woodstock Vacation Packages

Woodstock Hotel Deals

Wellsworth Hotel
Wellsworth Hotel
3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is ₩158,020 per night from Jul 2 to Jul 3
₩158,020
₩176,508 total
Jul 2 - Jul 3
includes taxes & fees
9/10 Wonderful! (1,205 reviews)
"The hotel was very nice. Really impressed with facilities and a great rate."

Reviewed on Jun 25, 2025

Wellsworth Hotel
Publick House Historic Inn and Country Motor Lodge
Publick House Historic Inn and Country Motor Lodge
2.5 out of 5
277 Main Street (RT 131), Sturbridge, MA
Fully refundableReserve now, pay when you stay
The price is ₩121,271 per night from Jun 30 to Jul 1
₩121,271
₩135,459 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (1,421 reviews)
"Great place to stay."

Reviewed on Jun 27, 2025

Publick House Historic Inn and Country Motor Lodge
Inn on Storrs
Inn on Storrs
3.5 out of 5
123 Storrs Road, Willimantic, CT
Fully refundableReserve now, pay when you stay
7.8/10 Good! (1,000 reviews)
"Simple and comfortable"

Reviewed on Jun 25, 2025

Get rates
Inn on Storrs
See all 280 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.

Frequently asked questions

How much does a Woodstock vacation package cost?
Offering excellent value package deals on Expedia, you'll be surprised at 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?
Plan your trip for the shoulder or low season and you're likely to score cheap Woodstock vacation packages. Remember that public holidays and local events and festivals can impact prices, so do your research before booking.
How many days is enough for Woodstock?
Usually, a handful of days is enough to check out the top attractions during your Woodstock vacation. However, if you prefer to have more time to rest or go on day trips, think about extending your trip.
Is it worth booking a vacation package to Woodstock?
From leading attractions such as Roseland Park Golf Course and Harrisville Golf Course to its terrific camping, a Woodstock vacation delivers big on experiences. With so much to do and see, it's time to find out for yourself why Woodstock is such a good vacation destination.
How to find the best Woodstock package deals?
Finding a cheap Woodstock package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most affordable Woodstock package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Woodstock vacation as a package?
You can enjoy significant savings on your next Woodstock getaway by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Woodstock?
If you've got your Woodstock vacation dates finalized, book as early as you can to bag some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Woodstock?

  1. Choose when to get away: Check your schedule and pack your bags. Your preferred season and the activities on offer will also help you decide when to vacation in Woodstock.
  2. Budget wisely: As well as the cost of your hotel, you should factor in other expenses. These include transportation, flights and food. Also, set aside a little extra for unexpected costs that could crop up during your trip to Woodstock.
  3. Decide how long to go away for: Now that you're more familiar with Woodstock, you can work out the right length of your vacation. Pull together a draft plan and give yourself enough time to cover everything you want to see.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find a Woodstock vacation package that brings all your bookings together.

Discover the most popular places to visit in Woodstock

Taylor Brooke Winery

You can enjoy a tasting or tour at Taylor Brooke Winery during your travels to Woodstock. While in this family-friendly area, you can savor the top-notch restaurants.

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