Woodstock Holidays

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Top Flight + Hotel Deals in Woodstock

Price found within the past 48 hours. Click for updated prices.
Mountain Lodge at Okemo, A Vail Resorts Property

Mountain Lodge at Okemo, A Vail Resorts Property

Clock Tower Base Area
€602
per person
10 Oct - 12 Oct
found 13 hours ago
Return direct flight included
New York (NYC) to Springfield (VSF)
8/10 Very good! (225 reviews)
Staff was very helpful, the property is very clean, the room was clean with lots of space. The kitchen had a full size refrigerator and microwave. I was very happy overall

Reviewed on 19 Jul 2026

Okemo Mountain Lodging by Vail Resorts

Okemo Mountain Lodging by Vail Resorts

Clock Tower Base Area
€762
per person
10 Oct - 12 Oct
found 13 hours ago
Return direct flight included
New York (NYC) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.

Reviewed on 26 Jun 2025

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area
€608
per person
10 Oct - 12 Oct
found 13 hours ago
Return direct flight included
New York (NYC) to Springfield (VSF)
8.6/10 Excellent! (880 reviews)
Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts

Clock Tower Base Area
€641
per person
10 Oct - 12 Oct
found 13 hours ago
Return direct flight included
New York (NYC) to Springfield (VSF)
7.8/10 Good! (35 reviews)
Okemo Westwood Condo 3 Bedroom Condo by RedAwning

Okemo Westwood Condo 3 Bedroom Condo by RedAwning

€1,157
per person
10 Oct - 12 Oct
found 13 hours ago
Return direct flight included
New York (NYC) to Springfield (VSF)
No reviews

Top hotels in Woodstock

Woodstock Inn & Resort

Woodstock Inn & Resort

Fourteen The Green Woodstock VT
€424
7 Sept - 8 Sept
includes taxes & fees
9.4/10 Exceptional! (599 reviews)
"Amazing! Will visit again."

Reviewed on 7 Aug 2026

Woodstock Inn & Resort
On The River Inn

On The River Inn

1653 West Woodstock Road Woodstock VT
€259
8 Sept - 9 Sept
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"This place was set up even better than I expected. With nature right outside the door, it was so relaxing and stress-free, and the overall atmosphere was elegant and beautiful. Staff members are very friendly, too. The only thing was that the mattress was a bit too soft, which gave me a ..."

Reviewed on 28 Aug 2026

On The River Inn
The Shire Woodstock

The Shire Woodstock

46 Pleasant St. Woodstock VT
Fully refundableReserve now, pay when you stay
€193
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (987 reviews)
"We enjoyed our stay very much. We found our stay to very quiet. The back of the property was so peaceful and relaxing sitting by the river, listening to the birds and the gurgling of the river as it moves along. The room was comfortable with a fridge and freezer for snacks/fruit etc. I'd like to ..."

Reviewed on 27 Aug 2026

The Shire Woodstock
See all 2,687 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 first-hand.
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A snow-covered mountain landscape with ski trails and trees.

Saskadena Six Ski Area

8.8/10 (35 reviews)
This historic ski area established in 1935 offers 23 trails across 100 acres of Vermont terrain. Enjoy a charming, low-key atmosphere with runs suitable for all skill levels and a cosy lodge experience.
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A calm lake surrounded by dense green forest and a clear sky.
Photo by Jessie Festa

Marsh-Billings-Rockefeller National Historical Park

9.4/10 (40 reviews)
Explore America's only national park dedicated to conservation history through its Victorian mansion and historic forest. Wander scenic carriage roads while discovering three generations of environmental stewardship.
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A lake with white birds and tall grasses.

Lakota Lake

8.0/10 (1 review)
This serene 15-acre reservoir sits amid private Vermont forest, dating back to 1891. Morning visits reward with calm waters and active wildlife, though advance arrangements through the Lakota Club are required.
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A wooden covered bridge with a sign reading "Woodstock Middle Bridge."

Ottaquechee River

9.4/10 (67 reviews)
Flowing through Vermont's countryside, the Ottauquechee River carves the dramatic Quechee Gorge, Vermont's deepest ravine. Stroll the riverside trail for serene views, especially during autumn.
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Woodstock Town Hall Theatre

9.4/10 (13 reviews)
This historic neoclassical theatre captivates with its outstanding natural acoustics and intimate 386-seat design. Enjoy live performances or first-run films while savouring the locally beloved maple butter popcorn.
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Middle Covered Bridge

You can learn about the history of Woodstock with a stop at Middle Covered Bridge. While in this quaint area, you can savour the top-notch restaurants.
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Red Wagon Toy Company

4.0/10 (2 reviews)
This whimsical Vermont toy shop offers a curated selection of unique playthings and the famous Rody bouncing toys. Browse quality educational items for infants to big kids in this charming Woodstock gem.
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Frequently asked questions

How much does a Woodstock holiday package cost?
Offering great value package deals from €602 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.

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