Woodstock Vacations

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    Save up to SARĀ 5,400 when you book a flight and hotel together*

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Find the Best Woodstock Vacation Packages

Woodstock Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is SARĀ 1,874 per night from Aug 2 to Aug 3
SARĀ 1,874
SARĀ 2,227 total
2 Aug - 3 Aug
includes taxes & fees
9.4/10 Exceptional! (590 reviews)
"As always - best hotel in Vermont."

Reviewed on 12 July 2026

Woodstock Inn & Resort
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
The price is SARĀ 911 per night from Jul 21 to Jul 22
SARĀ 911
SARĀ 1,084 total
21 Jul - 22 Jul
includes taxes & fees
9.4/10 Exceptional! (1,010 reviews)
"when we got to the hotel after a long day of travel we found that the bar and restaurant were closed those days of the week so had to buy chips for dinner. we found a cockroach in the room and when we put out the room cleaning notice, nobody came and cleaned. when we had a nice dinner my daughter ..."

Reviewed on 13 July 2026

On The River Inn
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
The price is SARĀ 928 per night from Aug 5 to Aug 6
SARĀ 928
SARĀ 1,102 total
5 Aug - 6 Aug
includes taxes & fees
8.8/10 Excellent! (965 reviews)
"Very nice property. Would be great to have coffee in the rooms. Also very limited hot water. Ran out a few times even after a quick shower."

Reviewed on 12 July 2026

The Shire Woodstock
See all 2,698 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.

Stay near popular Woodstock attractions

A herd of cows grazing in a fenced pasture with trees and a building in the background.

Billings Farm and Museum

9.2/10 (84 reviews)
This working dairy farm showcases Vermont's rural heritage through its historic 1890 Farm Manager's House. Watch cow milking, explore interactive exhibits, and experience traditional farming practices firsthand.
See properties

Frequently asked questions

How much does a Woodstock vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Woodstock costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Woodstock?
You can usually find lower prices and better availability in January, April and May. Take a look at our cheap Woodstock vacation packages and you could land some great off-season discounts.
How to find the best Woodstock package deals?
Use Expedia's handy filters to find some fabulous 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 want to save, plan your adventure for midweek, or search for Woodstock package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Woodstock vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking stays and flights separately. Better still, you can tailor your Woodstock getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Woodstock?
Secure fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Woodstock break.
How to plan a trip to Woodstock?

  1. Choose the ideal time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to travel to Woodstock.
  2. Budget wisely: Besides the price of your stay, you should consider other expenses too. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that could arise during your trip to Woodstock.
  3. Decide your trip length: Think about how long you'd like to spend exploring Woodstock. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your accommodations and airfare: Once you've settled on your travel dates and duration, book the ideal Woodstock vacation package for you.