South Woodstock Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in South Woodstock

Wellsworth Hotel
Wellsworth Hotel
3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is 3.035.899 ₫ per night from 6 Jul to 7 Jul
3.035.899 ₫
3.391.099 ₫ total
6 Jul - 7 Jul
includes taxes & fees
9/10 Wonderful! (1,203 reviews)
"Clean and the staff were great."

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 29 Jun to 30 Jun
2.329.876 ₫
2.602.472 ₫ total
29 Jun - 30 Jun
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 176 properties in South 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 South Woodstock holiday package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday to South Woodstock costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to South Woodstock?
January, February and March are great times to search for cheap South Woodstock holiday packages. Opting to travel in less busy periods means you'll typically find better prices on flights and hotels.
How many days is enough for South Woodstock?
With a well-organised itinerary, you can easily hit the most popular South Woodstock sights in a handful of days. But if you want to explore off the beaten track or go on day tours, consider booking your South Woodstock holiday for longer.
Is it worth booking a holiday package to South Woodstock?
It's easy to see why a South Woodstock holiday is on the to-do list of many travellers. Major attractions like Harrisville Golf Course are just the start of things to see and do here.
How to find the best South Woodstock package deals?
Use Expedia's filters to find some unbeatable South Woodstock package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for South Woodstock package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your holiday package well in advance.
Is it cheaper to book a South Woodstock holiday as a package?
You can enjoy significant savings on your next South Woodstock break by booking a tailored holiday package. Click on the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to South Woodstock?
If you're planning an impromptu South Woodstock adventure, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking ahead.
How to plan a trip to South Woodstock?

  1. Choose when to get away: Check your diary and get packing. Your preferred time of year and the type of activities available will also help you decide when to visit South Woodstock.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to activities and airfares. Your hotel will likely be the biggest expense during your trip to South Woodstock.
  3. Decide how long to go away for: Now that you're up to speed on South Woodstock, you can work out the right length of your holiday. Pull together a draft plan and allocate enough time for all the things you want to do.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick a South 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