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 AED 1,098 per night from Mar 16 to Mar 17
AED 1,098
AED 1,370 total
includes taxes & fees
16 Mar - 17 Mar
9.2/10 Wonderful! (502 reviews)
Perfect Spot
"The Woodstock Inn & Resort is the quintessential New England inn. Walk in the lobby and you are greeted by a large warm fire. The staff at all levels were gracious and helpful. The room was large, well decorated and extremely comfortable. Great location to walk downtown even with single digit temperatures. ..."

Reviewed on 22 February 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 AED 721 per night from Mar 5 to Mar 6
AED 721
AED 841 total
includes taxes & fees
5 Mar - 6 Mar
8.6/10 Excellent! (727 reviews)
"Great hotel, room was cute and with a nice view. 5 min walk to downtown. If we needed anything we just texted the front desk and they got us what we needed. Would stay again!"

Reviewed on 21 February 2025

The Shire Woodstock
Sleep Woodstock Motel
Sleep Woodstock Motel
2 out of 5
4324 West Woodstock Road, Woodstock, VT
Fully refundableReserve now, pay when you stay
The price is AED 375 per night from Mar 5 to Mar 6
AED 375
AED 412 total
includes taxes & fees
5 Mar - 6 Mar
9.6/10 Exceptional! (470 reviews)
"This place was adorable, and it was a very lucky find on the eve of a storm on a holiday weekend with 2 dogs in tow. Seems to be an old motel renovated. Cute decor. There were lots of cute helpful extras packed into a small space. Coffee, tea and Cider for the Keurig, retro mini fridge, garbage can ..."

Reviewed on 27 February 2025

Sleep Woodstock Motel
See all 2,586 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

Saskadena Six Ski Area

4.5/5(14 reviews)

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

Saskadena Six Ski Area