Woodstock Vacations from $625

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Your Woodstock Vacation

Book a Woodstock vacation package and get ready for a thrilling adventure. Known for its artistic creativity and lively atmosphere, there's plenty to keep you on the move in this city. A trip to Woodstock is a superb opportunity to sightsee. Check out renowned attractions like Saskadena Six Ski Area, Billings Farm and Museum and Sugarbush Farm. Stop dreaming and start adventuring. Explore the multitude of options on Expedia today and finally put your Woodstock vacation plans in motion!

The Latest Woodstock vacation packages

Price found within the past 48 hours. Click for updated prices.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $736, price is now $625 per person
$625
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (823 reviews)
Our room was clean and welcoming.

Reviewed on Oct 16, 2025

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $961, price is now $722 per person
$722
per person
Dec 5 - Dec 9
found 5 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Springfield (VSF)
9.2/10 Wonderful! (100 reviews)
The owner was so nice, and the chef made delicious dishes. Highly recommend!

Reviewed on Oct 13, 2025

Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
Clock Tower Base Area
Price was $926, price is now $758 per person
$758
per person
Dec 5 - Dec 9
found 5 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Springfield (VSF)
8/10 Very Good! (208 reviews)
We really enjoyed our stay at the Mountain Lodge at Okemo, it was clean and our room was newly renovated and very cute. Would definitely recommend!!

Reviewed on Oct 6, 2025

Modern & Updated Winterplace 3br- Sleeps 12 3 Bedroom Condo by RedAwning

Modern & Updated Winterplace 3br- Sleeps 12 3 Bedroom Condo by RedAwning

3.5 out of 5
Okemo Village
Price was $1,692, price is now $1,481 per person
$1,481
per person
Dec 5 - Dec 9
found 5 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Springfield (VSF)
No reviews
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
Price was $1,054, price is now $928 per person
$928
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (24 reviews)
I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place

Reviewed on Sep 15, 2025

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Discover the most popular places to visit in Woodstock

The house

Billings Farm and Museum

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

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

Saskadena Six Ski Area

Woodstock Hotel Deals

The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $156 total per night from Nov 16 to Nov 17
$156 total
Nov 16 - Nov 17
Total with taxes and fees
8.6/10 Excellent! (851 reviews)
"Easy check-in / check-out. Very clean property and rooms. Easily walkable location to every major point of interest in Woodstock. Highly recommend the property."

Reviewed on Oct 16, 2025

The Shire Woodstock
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$389 nightly
The price is $428 total per night from Nov 16 to Nov 17
$428 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (537 reviews)
"Beautiful hotel!! The staff, room, and spa were fantastic!!"

Reviewed on Oct 10, 2025

Woodstock Inn & Resort
The Jackson

The Jackson

4 out of 5
43 Senior Lane, Woodstock, VT
$149 nightly
The price is $164 total per night from Nov 4 to Nov 5
$164 total
Nov 4 - Nov 5
Total with taxes and fees
9.6/10 Exceptional! (235 reviews)
"The staff were incredible, so friendly and welcoming. Each night they served wine, cheese and crackers. The overall atmosphere and hospitality was amazing. We hated to leave."

Reviewed on Oct 7, 2025

The Jackson
See all 2,601 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.

Woodstock Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Population
870
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Saskadena Six Ski Area, Montshire Museum of Science and Woodstock Town Hall Theatre

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Frequently asked questions

How much does a Woodstock vacation package cost?
Offering great value package deals from $625 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?
You can generally find lower prices and better availability in July, November and December. Explore our cheap Woodstock vacation packages and you could score some great off-season deals.
How many days is enough for Woodstock?
For your Woodstock vacation, a handful of days will be enough to tour the top spots. Be sure to visit Marsh-Billings-Rockefeller National Historical Park — it's one of the major sights in this destination. If you're after more adventure, think about basing yourself here and heading off on some day tours from Woodstock.
Is it worth booking a vacation package to Woodstock?
Woodstock has all the ingredients you need for a memorable break — nature, hiking and views are just the start. Whether you'd like to check out attractions like Marsh-Billings-Rockefeller National Historical Park and Woodstock Town Hall Theatre, or venture off the beaten track, you'll find plenty to see and do on your Woodstock vacation.
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. Choose the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to visit Woodstock.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to airfares and activities. Your hotel will probably be the largest expense during your trip to Woodstock.
  3. Explore Woodstock with Expedia's trip planning tool: Gain insights into the top attractions and best stays for your trip to Woodstock. You can also save your favorite places, collaborate with friends and family and organize all your plans in one place.
  4. Work out your trip length: Consider how long you want to spend exploring Woodstock. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  5. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Woodstock vacation package that brings all your bookings together.
  6. Book experiences or activities ahead of time: Whether it's a ticket to a major attraction or a day trip, you won't have to worry about missing out on the best Woodstock has to offer. Find all the fun things to do in Woodstock with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Woodstock vacation packages?
Your Woodstock trip should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you a little more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

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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.