Woodstock Holidays

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Top hotels in Woodstock

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is S$705 per night from 10 Aug to 11 Aug
S$705
10 Aug - 11 Aug
includes taxes & fees
9.2/10 Wonderful! (523 reviews)
"Service and concierge were excellent. Property was kept in a beautiful condition. Lost of inspiring rooms."

Reviewed on 13 Jul, 2025

Woodstock Inn & Resort
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road, Woodstock, VT
The price is S$339 per night from 17 Jul to 18 Jul
S$339
17 Jul - 18 Jul
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Helpfulness of the staff was first class"

Reviewed on 13 Jul, 2025

On The River Inn
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
8.6/10 Excellent! (774 reviews)
"This is a lovely property in the town of Woodstock. We enjoyed our time there (and all the space in our room!). I left something in our room and did not realize it until the next day. I called the property to ask if anything had been found. They soon got back to me that they had my item and would ..."

Reviewed on 10 Jul, 2025

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The Shire Woodstock
See all 2,641 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.

Popular places to visit

Saskadena Six Ski Area

Hit the slopes in Woodstock with a visit to Saskadena Six Ski Area. Wander the riverfront in this quaint area.

Saskadena Six Ski Area

What to do in Woodstock

Transportation Tour from Woodstock to Windsor

Antiques and Artisans: A Woodstock to Windsor Self-Guided Drive

S$19
per traveller
Antiques and Artisans: A Woodstock to Windsor Self-Guided Drive
Signature Vermont Wayfinders Private Guided Tour

Signature Vermont Wayfinders Private Guided Tour

S$1,018
per traveller
Signature Vermont Wayfinders Private Guided Tour
See all activities in Woodstock

Frequently asked questions

How much does a Woodstock holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Woodstock costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Woodstock?
January, April and May are great times to look for cheap Woodstock holiday packages. Choosing to travel in less busy periods means you can usually find lower prices on flights and accommodation.
How many days is enough for Woodstock?
For your Woodstock holiday, a few days will be enough to tour the top spots. Be sure to visit Mount Tom Peak --- it's one of the top attractions in this destination. If you want more adventure, think about basing yourself here and setting off on some day trips from Woodstock.
Is it worth booking a holiday package to Woodstock?
Woodstock has everything you need for an awesome break --- nature, hiking and views are just the start. Whether you want to check out attractions like Billings Farm and Museum and Woodstock Town Hall Theatre, or take the road less traveled, you'll have plenty to do on your Woodstock holiday.
How to find the best Woodstock package deals?
Begin your search for a Woodstock package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Woodstock package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Woodstock escape off to a flying start.
Is it cheaper to book a Woodstock holiday as a package?
You can enjoy significant savings on your Woodstock retreat by booking a personalised holiday package. Check the "Package" heading, then select your travel dates and destination to see the best hotel and flight 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 Woodstock?
Score amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Woodstock escape.
How to plan a trip to Woodstock?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Woodstock.
  2. Plan your budget wisely: As well as the price of your hotel, you'll need to factor in other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Woodstock.
  3. Decide how long to go for: Now that you're up to speed on Woodstock, you can figure out the perfect length of your break. Put together a rough itinerary and allocate enough time for all the things you want to do.
  4. Combine your accommodation and airfare: After you've nailed down your trip dates and duration, lock in the right Woodstock holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.