Woodstock Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Woodstock

Wellsworth Hotel
Wellsworth Hotel
3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is 3.036.828 ₫ per night from 6 Jul to 7 Jul
3.036.828 ₫
3.392.137 ₫ total
6 Jul - 7 Jul
includes taxes & fees
9/10 Wonderful! (1,195 reviews)
"The hotel itself was beautiful and clean and the staff were amazing. The bartender (sorry that I don’t remember her name) made the most delicious rum and juice drink I’ve ever had. The immediate area around the hotel is less impressive, but we never felt unsafe."

Reviewed on 23 Jun 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 2.329.876 ₫ per night from 27 Jul to 28 Jul
2.329.876 ₫
2.602.472 ₫ total
27 Jul - 28 Jul
includes taxes & fees
8.6/10 Excellent! (1,424 reviews)
"The old building was beautiful and the restaurant, bar and bakery were great."

Reviewed on 23 Jun 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! (1,006 reviews)
"Very clean. Eaay check in."

Reviewed on 22 Jun 2025

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Inn on Storrs
See all 279 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 holiday package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday to Woodstock costs! Our packages simplify travel planning and maximise 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 holiday 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 holiday. 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 holiday package to Woodstock?
From leading attractions such as Roseland Park Golf Course and Harrisville Golf Course to its terrific camping, a Woodstock holiday 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 holiday 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," "Traveller 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Woodstock holiday as a package?
You can enjoy significant savings on your next Woodstock getaway by booking a personalised holiday 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 holiday package to Woodstock?
If you've got your Woodstock holiday 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 holiday 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 holiday. 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 holiday package that brings all your bookings together.

Popular places to visit

Roseland Park Golf Course

Enjoy a round of golf in Woodstock at Roseland Park Golf Course. Visit the lively bars or top-notch restaurants in this family-friendly area.

Roseland Park Golf Course

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 savour the top-notch restaurants.

Taylor Brooke Winery

Roseland Cottage

You can study the exhibits at Roseland Cottage, a museum with a storied past, during your holiday in Woodstock. Visit the lively bars or top-notch restaurants in this quaint area.

Roseland Cottage