Woodstock Vacation Packages
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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!
Top Woodstock Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Latchis Hotel
CA $964
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Springfield (VSF)
8.6/10 Excellent! (974 reviews)
This hotel is a great representation of a niche throw back. Record players in the room. Stacks of records in the hall to enjoy. The lobby is beautiful and they are attached to the movie theatre, which is old school and beautiful to witness. The hotel is in a TERRIBLE AREA and in fact Brattleboro, VT has an extremely large homeless and drug population. I truly feel for the business’ in the town. No foot traffic. We didn’t see one police vehicle at all. Multiple people told us to keep our wits about us if walking at night. The restaurants that we did visit have lovely people and are friendly but the places to see are not worth a visit to this sad town. It’s truly unfortunate too. You have this idea of small town in New England with shops and mom and pop places to eat and this had almost NONE of that.
Reviewed on Sep 11, 2026
Holiday Inn Express Hotel & Suites Brattleboro by IHG
CA $1,164
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Springfield (VSF)
9/10 Wonderful! (1,001 reviews)
Todo muy bien me encanta este cadena de hoteles, nunca he tenido problemas con ellos
Reviewed on Sep 9, 2026
Ready to book your vacation to Woodstock?
Woodstock Hotel Deals
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
CA $732
CA $866 total
Sep 14 - Sep 15
includes taxes & fees
The Jackson
43 Senior Lane Woodstock VT
CA $333
CA $366 total
Sep 14 - Sep 15
includes taxes & fees
9.6/10 Exceptional! (315 reviews)
"It’s an overpriced hotel with zero staff. Also it’s about a mile outside town."
Reviewed on Sep 11, 2026
The Shire Woodstock
46 Pleasant St. Woodstock VT
Fully refundableReserve now, pay when you stay
CA $216
CA $257 total
Sep 13 - Sep 14
includes taxes & fees
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
Billings Farm and Museum
9.2/10 (84 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.
Saskadena Six Ski Area
8.8/10 (35 reviews)
Hit the slopes in Woodstock with a visit to Saskadena Six Ski Area. Wander the riverfront in this quaint area.
Photo by Jessie Festa
Marsh-Billings-Rockefeller National Historical Park
9.4/10 (40 reviews)
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.
Lakota Lake
8.0/10 (1 review)
Commune with nature and explore the great outdoors at Lakota Lake during your travels in Woodstock. While in this quaint area, you can savor the top-notch restaurants.
Ottaquechee River
9.4/10 (67 reviews)
Explore the great outdoors at Ottaquechee River and enjoy the mountain views during your trip to Woodstock. Amble around this quaint area's riverfront, or seek out the ski slopes.
Woodstock Town Hall Theatre
9.4/10 (13 reviews)
Get tickets for a show at Woodstock Town Hall Theatre, a theater with a story to tell in Woodstock. Wander the riverfront in this quaint area.
Middle Covered Bridge
You can learn about the history of Woodstock when you stop by Middle Covered Bridge. While in this quaint area, you can savor the top-notch restaurants.
Taftsville Covered Bridge
9.6/10 (45 reviews)
Taftsville Covered Bridge is just one of the places to see in Taftsville, so why not enjoy the other things to explore during your travels? Wander the riverfront or discover the area's countryside.
Frequently asked questions
How much does a Woodstock vacation package cost?
Offering excellent value package deals from CA $888 on Expedia, you'll be thrilled with how little 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 usually find lower prices and better availability in January, April and May. Take a look at our cheap Woodstock vacation packages and you could land some great off-season discounts.
How many days is enough for Woodstock?
Typically, a few days is ideal for a Woodstock vacation. With a well-planned itinerary, you can check out all the top sights such as Billings Farm and Museum, as well as discover some hidden treasures along the way.
Is it worth booking a vacation package to Woodstock?
Popular for its nature, hiking and views, a Woodstock vacation is a hit with all kinds of visitors. Be sure to check out major sights like Billings Farm and Museum and Woodstock Town Hall Theatre, and consider renting a set of wheels for day trips to explore even more.
How to find the best Woodstock package deals?
Use Expedia's handy filters to find some fabulous Woodstock package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Woodstock package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Woodstock vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking stays and flights separately. Better still, you can tailor your Woodstock getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Woodstock?
Secure fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Woodstock break.
How to plan a trip to Woodstock?
- Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Woodstock.
- Budget wisely: Besides the price of your stay, you should consider other expenses too. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that could arise during your trip to Woodstock.
- Decide your trip length: Think about how long you'd like to spend exploring Woodstock. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Combine your accommodations and airfare: Once you've settled on your travel dates and duration, book the ideal Woodstock vacation 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.
