Woodstock Holidays

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Your Woodstock Holiday

Build a custom holiday package to Woodstock and get ready to experience this amazing city your way. Think about spending time in the neighbourhood of Killingly, which is good for nature and more. Any trip to Woodstock needs a well-designed itinerary. Fill yours with leading attractions like Taylor Brooke Winery, Roseland Park Golf Course and Little River Plaza Shopping Centre. No matter your travel plans or budget, organising a tailored Woodstock holiday is a breeze with Expedia.

Woodstock Holiday

Woodstock Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Taylor Brooke Winery, Roseland Park Golf Course and Harrisville Golf Course

Our pick of the best Woodstock Hotel Deals

Secluded 2-Acre Lakefront Home! Book Your Retreat!
Secluded 2-Acre Lakefront Home! Book Your Retreat!
Woodstock
9.8/10 Exceptional! (65 reviews)
Just what we needed
"The property is very nice and roomy. If you have a big family like ours and you need a place in this part of CT, you’re in luck."

Reviewed on 21 Jun. 2025

Get rates
Secluded 2-Acre Lakefront Home! Book Your Retreat!
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 AU$152 per night from 20 July to 21 July
AU$152
20 July - 21 July
includes taxes & fees
8.8/10 Excellent! (1,437 reviews)
"I had originally booked a room in the Motor Lodge because it was the cheapest. I was only staying for one night as a stopover on my way to Canada. There was an issue with over- booking so they upgraded me to The Chamberlain House for the same price. It was a very nice room and very quiet. The staff ..."

Reviewed on 8 Jul. 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 AU$183 per night from 20 July to 21 July
AU$183
20 July - 21 July
includes taxes & fees
9/10 Wonderful! (1,229 reviews)
"Liked quiet. Disliked no included breakfast."

Reviewed on 10 Jul. 2025

Wellsworth Hotel
See all 278 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 Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Discover the most popular places to visit in Woodstock

Little River Plaza Shopping Center

You can find the perfect gifts to bring home at Little River Plaza Shopping Center during your visit to South Woodstock. While in this quaint area, you can savour 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. Visit the top-notch restaurants or lively bars in this quaint area.

Roseland Park Golf Course

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.

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