Woodstock Holidays

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Woodstock Holiday

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
The price is NZ$1,219 per night from 29 June to 30 June
NZ$1,219
29 June - 30 June
includes taxes & fees
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

Secluded 2-Acre Lakefront Home! Book Your Retreat!
Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn
Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn
Woodstock
10/10 Exceptional! (4 reviews)
Cozy spot in NE Connecticut
"We had a delightful two night stay while in the area for a wedding. Great spot and a responsive host."

Reviewed on 22 Jun. 2025

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Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn
Wellsworth Hotel
Wellsworth Hotel
3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is NZ$214 per night from 1 July to 2 July
NZ$214
1 July - 2 July
includes taxes & fees
9/10 Wonderful! (1,202 reviews)
"Clean and the staff were great."

Reviewed on 23 Jun. 2025

Wellsworth Hotel
See all 280 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.

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