Woodstock Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

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 Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Woodstock CT
The price is AU$895 per night from 3 Mar to 4 Mar
AU$895
3 Mar - 4 Mar
includes taxes & fees
9.8/10 Exceptional! (81 reviews)
We had a great stay! Clean and very comfortable. The big kitchen was equipped with everything you’d need and had a big table for hosting the whole family.

Reviewed on 13 Jan 2026

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!

Woodstock CT
The price is AU$866 per night from 3 Mar to 4 Mar
AU$866
3 Mar - 4 Mar
includes taxes & fees
10/10 Exceptional! (22 reviews)
Welcoming host! Beautiful house with great amenities!

Reviewed on 24 Feb 2026

Stunning Lakefront Escape! Book Your Dream Getaway!
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St Southbridge MA
Fully refundableReserve now, pay when you stay
The price is AU$168 per night from 3 Mar to 4 Mar
AU$168
3 Mar - 4 Mar
includes taxes & fees
9.2/10 Wonderful! (1,437 reviews)
Clean room Beautiful hotel

Reviewed on 2 Mar 2026

Wellsworth Hotel
See all 314 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

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

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 family-friendly area, you can savour the top-notch restaurants.

Little River Plaza Shopping Center

Explore a world of travel with Expedia

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