Woodstock Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Find the Best Woodstock Vacation Packages
Woodstock Hotel Deals
Getaway Lakefront Home for Skiing or Summer Enjoyment
Bryant Pond ME
10/10 Exceptional! (62 reviews)
"Perfect house for our family vacation. There was plenty of room inside and out for our four famlies. Beautiful views of the water from the house and dock. Enjoyed amazing sunsets every day."
Reviewed on Jul 13, 2026
Oxford Casino Hotel
777 Casino Way Oxford ME
Fully refundableReserve now, pay when you stay
￥17,400
￥18,966 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"Hotel was good and casino was fun. Wish there would have been more choices to eat or even a mini convenient store like they have at airports on location."
Reviewed on Aug 8, 2026
Hampton Inn Oxford
151 Main St Oxford ME
Fully refundableReserve now, pay when you stay
￥17,981
￥19,599 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (1,013 reviews)
"There was a dog barking late at night in the roim next to me. Then a couple were yelling at each other from 1AM till at least 3AM. My key didn't work at the back parking lot door. I had to walk all around to the front of the building 3 times. The guy at the desk reset my card key twice before coming ..."
Reviewed on Aug 9, 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.
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.
Mineral Collector
6.0/10 (1 review)
Enjoy an outing to Mineral Collector during your stay in Woodstock. Stroll along the riverfront or discover the mountain views in this relaxing area.
Frequently asked questions
How much does a Woodstock vacation package cost?
You'll find cheap prices 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?
If you're hoping to book a cheap Woodstock vacation package, consider planning a trip in May, September and November. You're likely to find lower prices on airfares and hotels during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Woodstock?
Typically, a handful of days is enough to go to the main attractions during your Woodstock vacation. However, if you'd like to have time to rest or take day trips, consider extending your trip.
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.
How to plan a trip to Woodstock?
- Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Woodstock.
- Work out your budget: Make sure you have enough money to pay for everything from food and transportation to flights and activities. Your hotel will likely be the largest expense during your trip to Woodstock.
- Decide how long to go for: Now that you know more about Woodstock, you can figure out the perfect length of your break. Pull together a rough itinerary and allocate enough time for all the things you want to do.
- Combine your accommodations and airfare: Once you've settled on your travel dates and duration, lock in the right Woodstock vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
