Woodstock Trips (flight + hotel)

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Top hotels in Woodstock

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 P5,182 per night from Aug 6 to Aug 7
P5,182
P5,789 total
Aug 6 - Aug 7
includes taxes & fees
8.8/10 Excellent! (1,466 reviews)
"Very clean and quiet despite it being a busy place. We ate at the Tavern which served great scallops. Landscape very attractive."

Reviewed on Aug 3, 2025

Publick House Historic Inn and Country Motor Lodge
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is P6,922 per night from Aug 10 to Aug 11
P6,922
P7,731 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (1,259 reviews)
Beautiful and comfortable hote'
"Beautiful, comfortable and cozy hotel. Room was great and clean. The only mishap was that we had to wait some time to checkin since there was nobody at the counter. Clerk wasn't the friendliest one."

Reviewed on Aug 2, 2025

Wellsworth Hotel
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! (1,002 reviews)
"I stay here every year at the same time, over 10 yrs. The hotel has gotten better. Nothing fancy but does the trick for a good nights sleep and clean bathroom."

Reviewed on Aug 1, 2025

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Inn on Storrs
See all 276 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.

Popular places to visit

Little River Plaza Shopping Center

You can browse for the perfect souvenirs at Little River Plaza Shopping Center during your visit to South Woodstock. While in this quaint area, you can savor the top-notch restaurants.

Little River Plaza Shopping Center

Roseland Park Golf Course

Enjoy a round of golf in Woodstock at Roseland Park Golf Course. Check out the top-notch restaurants or lively bars in this quaint area.

Roseland Park Golf Course

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.

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