Woodstock Vacations from $710

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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.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $906, price is now $710 per person
$710
per person
Jan 20 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (VSF)
8.6/10 Excellent! (1,011 reviews)

Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
Price was $1,256, price is now $757 per person
$757
per person
Dec 16 - Dec 20
found 4 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Springfield (VSF)
8.8/10 Excellent! (111 reviews)
The hotel was amazing and the staff was so kind. Luke was working the front desk and made sure we had everything we needed. The hotel and property are beautiful. We really enjoyed our time and can't wait to come back!

Reviewed on Nov 8, 2026

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $1,016, price is now $796 per person
$796
per person
Dec 16 - Dec 20
found 4 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Springfield (VSF)
10/10 Exceptional! (250 reviews)
Viking Village is perfect in every way! If you're looking for a relaxed retreat, trails, nature, and delightfully detailed cabins and buildings, this is your dream stay. As you drive up toward the gates a sense of anticipation builds until the stockade fence and gate comes into view. It truly looks like you've traveled back in time once you arrive. Every cabin is slightly different. A raised walkway was thoughtfully built along the fronts of the cabins so you can avoid any snow or dirt as you come and go. Check-in is quick and Christina also gave us recommendations of nearby places to see or dine. The kitchenette does have what you'd need to cook and eat with for 4 people. Cabins are immaculate. Beds were comfortable. We made it a point to go out for the morning and evening feeding of the sheep. They may have been my favorite part of the stay! especially the lambs! We stayed 2 nights and enjoyed chatting with other guests around the firepit in the evening. (Their kids absolutely LOVED this place.) My husband and I are in our sixties and found the trails a little challenging! Quite hilly, but well marked. A heartfelt thank you to the folks running the Village. You were gracious hosts and made this someplace that we want to return to again! (Easier to get to than Iceland!)

Reviewed on Nov 7, 2026

Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was $1,168, price is now $961 per person
$961
per person
Dec 20 - Dec 27
found 6 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Springfield (VSF)
9.4/10 Exceptional! (138 reviews)

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 out of 5
Price was $995, price is now $842 per person
$842
per person
Jan 20 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (VSF)
9/10 Wonderful! (1,001 reviews)
Easy check in, clean room and nice location

Reviewed on Nov 9, 2026

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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 firsthand.
See properties

Woodstock Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$369 nightly
The price is $406 total per night from Nov 30 to Dec 1
$406 total
Nov 30 - Dec 1
Total with taxes and fees
Woodstock Inn & Resort
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$158 nightly
The price is $174 total per night from Nov 15 to Nov 16
$174 total
Nov 15 - Nov 16
Total with taxes and fees
9.2/10 Wonderful! (1,007 reviews)
"Clean-safe-great pool sauna and spa. Excellent dinner and breakfast. Comfortable bed, quiet, friendly staff."

Reviewed on Nov 8, 2026

On The River Inn
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $178 total per night from Nov 22 to Nov 23
$178 total
Nov 22 - Nov 23
Total with taxes and fees
The Shire Woodstock
See all 2,745 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

Things to do in and around Woodstock

Woodstock, Vermont, is a fantastic destination for outdoor enthusiasts, offering thrilling adventures such as skiing at its renowned ski resorts and fields. Visitors can explore various activities, including guided tours and day trips that showcase the area's natural beauty. Whether you're seeking adrenaline-pumping experiences or a relaxing getaway, Woodstock provides a perfect blend of adventure and leisure for an unforgettable vacation.

Shopping

In Woodstock, you can shop at Red Wagon Toy Company for unique toys and gifts. For a short drive, visit Quechee Gorge Village, just 6 miles away. If you're up for a drive, King Arthur Baking Company, located 12 miles away, offers delightful baking supplies and treats.

Recreation

Experience the charm of the Woodstock Town Hall Theatre, where culture and entertainment blend for a delightful evening. Enjoy outdoor sports and picturesque views at the Woodstock Country Club, perfect for golf enthusiasts. For family-friendly fun, visit the Upper Valley Aquatic Center, offering a refreshing aquatic experience just 9 miles away.

Adventure

Experience thrilling skiing at Killington Resort, located 14 miles from Woodstock, or enjoy the local slopes at Saskadena Six Ski Area. For a different adventure, challenge yourself at the Green Mountain Rock Climbing Center, only 3 miles away, where outdoor sports meet excitement.

Nightlife

In Woodstock, Vermont, experience a quaint nightlife with cozy taverns and charming pubs. Visit the Woodstock Inn's bar for craft cocktails or enjoy live music at local venues. The warm, inviting atmosphere makes for a perfect evening after exploring the beautiful town's daytime attractions.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Woodstock

Woodstock, Vermont, is a perfect destination for ski enthusiasts and outdoor adventurers. Explore its rich culture and history by visiting local attractions, including national parks, historic colleges, and iconic bridges. Whether you're traveling with family or seeking a unique experience, Woodstock offers a variety of activities that cater to all interests, making it an ideal spot for your next vacation.

  • Quechee Gorge Bridge: Experience breathtaking views at Quechee Gorge Bridge, a stunning canyon located 6 miles from Woodstock. The bridge offers outdoor adventures and picturesque scenery, making it a perfect spot for hiking and photography enthusiasts.
  • Dartmouth College: Located 13 miles away, Dartmouth College is a historic campus rich in culture and tradition. Stroll through its charming grounds, admire the architecture, and soak in the vibrant academic atmosphere while exploring the college's museums and galleries.
  • Billings Farm and Museum: Situated within Woodstock, Billings Farm and Museum brings the region's agricultural history to life. Enjoy interactive exhibits, farm animals, and seasonal events that celebrate rural heritage, making it an enriching experience for visitors of all ages.

Best time to go to Woodstock

The best time to visit Woodstock is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.6°F (-6.9°C)Light RainMostly CloudyAverageAverage
February21.6°F (-5.8°C)Light RainMostly CloudySlightly LowSlightly High
March29.7°F (-1.3°C)Light RainMostly CloudySlightly LowAverage
April42.1°F (5.6°C)Light RainMostly CloudySlightly LowSlightly Low
May55.2°F (12.9°C)Light RainMostly SunnyAverageSlightly Low
June62.8°F (17.1°C)Light RainMostly SunnyAverageAverage
July68.7°F (20.4°C)Light RainMostly SunnySlightly HighAverage
August66.9°F (19.4°C)Light RainMostly SunnyAverageAverage
September59.7°F (15.4°C)Light RainMostly SunnySlightly HighAverage
October48.0°F (8.9°C)Light RainMostly CloudySlightly HighSlightly High
November35.4°F (1.9°C)Light RainMostly SunnyAverageSlightly Low
December26.8°F (-2.9°C)Light RainMostly CloudyAverageSlightly High

Tips to save on your trip to Woodstock

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically April to May and November) for more affordable package holidays to Woodstock.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

What's included in a Woodstock vacation package?
A Woodstock vacation package lets you combine round-trip flights, hotel stays, and rental cars. Nearly a third of package hotels in Woodstock offer mountain views, enhancing the scenic experience of this ski destination. Many hotels also provide free breakfast, and some offer airport shuttle services to and from nearby airports like Albany International Airport (ALB).

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a Woodstock vacation package?
When you bundle, you can save up to 30%*. To save money on a Woodstock package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's the best vacation package for Woodstock?
For a luxury Woodstock vacation package, consider a stay at the 4.5-star Woodstock Inn & Resort, rated 8.9 out of 10. This resort, costing around $1,080 per night, offers an indoor pool, hot tub, and a bar/lounge, with travelers frequently praising its wonderful food and facilities.

Families seeking a Woodstock vacation package might enjoy the 4-star On The River Inn, rated 8.6 out of 10 and priced around $450 per night. It features family rooms, a playground, an indoor pool, and a game room, with travelers highlighting its cozy rooms and awesome food.

Couples looking for a romantic Woodstock vacation package could opt for the 4-star The Village Inn of Woodstock, rated 9.3 out of 10 and around $540 per night. This inn provides a bar/lounge and a game room, and travelers often note the amazing staff and its perfect weekend getaway atmosphere.

For a best value Woodstock vacation package, the Sleep Woodstock Motel is a great choice, rated 8.8 out of 10 and available for around $160 per night. It offers a kitchenette and is pet-friendly, with travelers consistently praising its super clean rooms and great value.

*Package availability and prices may change depending on dates and demand.
What's included in a Woodstock ski vacation package?
Woodstock ski vacation packages typically bundle flights and lodging, offering a convenient way to plan your trip to this ski destination. These packages focus on providing comfortable stays in properties suitable for enjoying the area's winter sports. While specific inclusions can vary, lift tickets, equipment rentals, and lessons are generally added separately, allowing you to customize your Woodstock vacation package to fit your needs.
Which Woodstock vacation packages include a mountain view?
Many Woodstock vacation packages include hotels with mountain-view rooms, with nearly a third of package hotels offering this amenity. For example, Woodbridge Inn, rated 9.4 out of 10 by travelers, provides options for mountain views and includes free breakfast and an outdoor pool; travelers often highlight the great staff and wonderful location. Another strong choice is the 4-star The Village Inn of Woodstock, rated 9.3 out of 10, which also offers mountain-view rooms and features a bar/lounge and free breakfast, praised by travelers for its amazing staff and being a perfect weekend getaway. Remember that specific room types and views depend on the package selected.
What are the top things to do in Woodstock?
A Woodstock vacation can be filled with outdoor adventure, history, and scenic beauty:

Browse and book things to do in Woodstock on Expedia.
Do you need to rent a car in Woodstock, or is public transport enough?
For a Woodstock vacation package with flights, a rental car offers the most flexibility, especially if you plan to explore beyond the village center. While many points of interest within the village are accessible by moderate walking, outer areas like South Woodstock are best reached by car. The terrain also features many hills, making a mountain bike a better option for longer distances if you choose to cycle.

Since Woodstock is primarily a ski destination outside a major city, having your own vehicle allows you to easily access ski resorts and other outdoor activities at your own pace.
Are Woodstock vacation package hotels conveniently located?
Woodstock vacation package hotels offer a range of locations, with many properties conveniently situated near the village center.

For example, the 4.5-star Woodstock Inn & Resort is about a 5-minute walk from central Woodstock, offering easy access to local attractions. The 4-star The Village Inn of Woodstock is also well-located, about a 10-minute walk from the center. If you prefer a slightly more secluded stay, Woodbridge Inn is about 6 miles from central Woodstock. This variety allows you to choose a package that best fits your preferred proximity to the village's amenities.
Can I change or cancel my Woodstock vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Woodstock vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Woodstock vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Woodstock vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Woodstock?
To find last-minute vacation packages to Woodstock, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Woodstock vacation packages?
Free cancellation on a Woodstock vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Woodstock vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Woodstock getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Woodstock vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.