Woodstock Vacations from $621
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Your Woodstock Vacation
Enjoy unforgettable adventures when you reserve a vacation package to Woodstock. Whether you're a foodie, history buff or just a traveler who appreciates new places, there's something for everyone in this vibrant city. Be sure to do some sightseeing during your trip to Woodstock. Shagg Pond and Concord Pond are some favorite places to visit. That dream Woodstock vacation is just clicks away. Explore accommodations, flights and more on Expedia for an adventure that's tailored just for you.
The Latest Woodstock vacation packages
Price found within the past 48 hours. Click for updated prices.
Pleasant Point Inn
$621
per person
Dec 11 - Dec 13
found 7 hours ago
Roundtrip flight included
Baltimore (BWI) to Auburn (LEW)
9.6/10 Exceptional! (4 reviews)
Experienced Maine for the first time and found this lovely inn in a small community. Will definitely be planning a trip back.
Reviewed on Jul 12, 2026
Stay near popular Woodstock attractions
Concord Pond
Commune with nature and explore the great outdoors at Concord Pond during your travels in Woodstock.
Shagg Pond
10.0/10 (1 review)
Commune with nature and explore the great outdoors at Shagg Pond during your travels in Woodstock. Stroll along the riverfront or experience the area's festivals.
Bryant Pond
Commune with nature and explore the great outdoors at Bryant Pond during your travels in Woodstock.
North Pond
Commune with nature and explore the great outdoors at North Pond during your travels in Woodstock.
Woodstock Hotel Deals
Oxford Casino Hotel
777 Casino Way Oxford ME
Fully refundableReserve now, pay when you stay
$116 nightly
$127 total
Oct 12 - Oct 13
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
"."
Reviewed on Sep 19, 2026
Grand Summit Hotel
97 Summit Road Newry ME
$127 nightly
$138 total
Sep 27 - Sep 28
Total with taxes and fees
8.4/10 Very Good! (415 reviews)
"Hotel common space looked newly renovated"
Reviewed on Sep 20, 2026
Jordan Hotel
27 Grand Circle Newry ME
$135 nightly
$146 total
Sep 27 - Sep 28
Total with taxes and fees
8.8/10 Excellent! (572 reviews)
"We stayed for two nights and had a great time. We stayed in a suite with a kitchenette. It was a very long walk down to the end of the building. I was just recovering from a knee injury so the walk from a far away parking lot and then all the way down the end of the building was not ideal. I did ..."
Reviewed on Sep 23, 2026
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 |
Population | 1,250 |
Top Sights | Concord Pond and Shagg Pond |
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Frequently asked questions
How much does a Woodstock vacation package cost?
You'll find cheap prices from $621 on Expedia for your Woodstock getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Woodstock costs.
What are the cheapest months to go to Woodstock?
You can generally find reduced prices and better availability in October, November and December. Take a look at our cheap Woodstock vacation packages and you could score some great off-season deals.
How many days is enough for Woodstock?
Usually, a handful of days is enough to check out the top sights during your Woodstock vacation. But if you prefer to have time to chill out or go on day trips, consider extending your itinerary.
How to find the best Woodstock package deals?
Use Expedia's handy filters to find some unbeatable Woodstock package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Woodstock package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually 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 land you great savings when compared to booking stays and flights separately. Better still, you can tailor your Woodstock getaway to match your exact style. Pick 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 reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Woodstock vacation.
Does Expedia offer Book Now, Pay Later Woodstock vacation packages?
Set off on your dream escape to Woodstock with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait until the next payday — we've teamed up with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no hidden or late payment fees, you can easily stick to your budget and snag great deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
