Woodstock Vacations

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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 SAR 1,122 per night from May 26 to May 27
SAR 1,122
SAR 1,399 total
includes taxes & fees
26 May - 27 May
9.2/10 Wonderful! (512 reviews)
"The Woodstock Inn is beautiful. Nice having access to the Athletic Club and a shuttle."

Reviewed on 22 April 2025

Woodstock Inn & Resort
The Shire Woodstock
The Shire Woodstock
3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
The price is SAR 436 per night from May 7 to May 8
SAR 436
SAR 508 total
includes taxes & fees
7 May - 8 May
8.6/10 Excellent! (734 reviews)
"The property is well maintained. Its staff is so friendly and helpful as well. We loved The River House with the beautiful terrace and rocking chairs overlooking the river. So peaceful. The amenities and sitting room were a lovely touch."

Reviewed on 14 April 2025

The Shire Woodstock
506 On the River Inn
506 On the River Inn
4 out of 5
1653 West Woodstock Road, Woodstock, VT
The price is SAR 540 per night from Apr 27 to Apr 28
SAR 540
SAR 732 total
includes taxes & fees
27 Apr - 28 Apr
9.2/10 Wonderful! (991 reviews)
Perfect Weekend Escape
"We had a wonderful weekend away here! The Inn is beautiful, charming/well decorated, has fabulous amenities (hot tub, pool, sauna, game room with arcades, lovely library, outdoor firepit, etc.) stunning views of the river, comfortable rooms and includes an incredible complementary breakfast. Hands ..."

Reviewed on 13 April 2025

506 On the River Inn
See all 2,640 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 vacation package cost?
Offering great value package deals on Expedia, you’ll be pleasantly surprised at how much 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?
January, April and May are great times to look for cheap Woodstock vacation packages. Choosing to travel in less busy periods means you can usually find lower prices on flights and accommodations.
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 vacation as a package?
You can enjoy significant savings on your Woodstock retreat by booking a personalized vacation package. Check the “Package” heading, then select your travel dates and destination to see the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation 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 accommodations and airfare: After you’ve nailed down your trip dates and duration, lock in the right Woodstock vacation package for you.

Discover the most popular places to visit in Woodstock

The house

Billings Farm and Museum

4.5/5(13 reviews)

You can study the exhibits at Billings Farm and Museum, a museum with a storied past, during your trip to Woodstock. Wander the riverfront in this quaint area.

Billings Farm and Museum
When visiting Woodstock, Vermont, one not-to-miss outdoor attraction is the Marsh - Billings - Rockefeller National Historical Park, the first National Park in Vermont. The site is full of ambient trails with different atmospheres, whether you want to summit a mountain, run through a field or picnic on a lovely lake. Here you see The Pogue, a 14-acre

Marsh-Billings-Rockefeller National Historical Park

Explore the lovely green spaces of Marsh-Billings-Rockefeller National Historical Park and enjoy the ski slopes in Woodstock. Stroll along the riverfront or discover the mountain views in this quaint area.

Marsh-Billings-Rockefeller National Historical Park

Woodstock Town Hall Theatre

4.5/5(5 reviews)

Get tickets for a show at Woodstock Town Hall Theatre, a theater with a story to tell in Woodstock. Wander the riverfront in this quaint area.

Woodstock Town Hall Theatre