Woodstock Vacations from $670

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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.
Lincoln Inn & Gallery

Lincoln Inn & Gallery

2 out of 5
West Woodstock
Price was $760, price is now $670 per person
$670
per person
Feb 26 - Mar 1
found 3 hours ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
8.8/10 Excellent! (56 reviews)
The Lincoln Inn was in a great area outside of Woodstock. The grounds are beautiful, and a covered bridge is only a short walk from the property. The rooms were very clean and comfortable.

Reviewed on Oct 19, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $864, price is now $681 per person
$681
per person
Feb 26 - Mar 1
found 3 hours ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
Clean and spacious room. Check-in was quick and staff were kind and helpful.

Reviewed on Dec 24, 2025

Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
Clock Tower Base Area
Save 100% on your flight
Price was $2,230, price is now $1,791 per person
$1,791
per person
Feb 26 - Mar 1
found 3 hours ago
Roundtrip non-stop 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 Jun 26, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $1,474, price is now $1,212 per person
$1,212
per person
Feb 26 - Mar 1
found 3 hours ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Clean, staff was great.

Reviewed on Dec 23, 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,227, price is now $1,014 per person
$1,014
per person
Feb 26 - Mar 1
found 3 hours ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
9.2/10 Wonderful! (549 reviews)
Luxurious and friendly resort! Loved it

Reviewed on Dec 18, 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

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$359 nightly
The price is $395 total per night from Jan 19 to Jan 20
$395 total
Jan 19 - Jan 20, 2026
Total with taxes and fees
9.2/10 Wonderful! (558 reviews)
Luxurious and friendly resort! Loved it

Reviewed on Dec 18, 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
$157 nightly
The price is $172 total per night from Jan 12 to Jan 13
$172 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
8.6/10 Excellent! (891 reviews)
The staff was super nice and flexible! Location was great

Reviewed on Dec 13, 2025

The Shire Woodstock
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$252 nightly
The price is $278 total per night from Jan 11 to Jan 12
$278 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
Rearaurant staff was top notch.

Reviewed on Dec 22, 2025

On The River Inn
See all 2,661 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.

Find the Best Woodstock Vacation Packages

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 $670 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.