Woodstock Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
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.
Ready to book your vacation to Woodstock?
Woodstock Hotel Deals
Grand Summit Hotel
97 Summit Road Newry ME
CA $159
CA $193 total
Sep 29 - Sep 30
includes taxes & fees
8.4/10 Very good! (411 reviews)
"I am very happy with this location for the price. Went in September before the ski season. Got a good price for a 3 days stay. Lots of stuff to do in the area for hiking and exploring. Hwy 17 is close and it is one of the most beautiful drives in the US (IMHO). There was a few parts of the hotel ..."
Reviewed on Sep 8, 2026
Oxford Casino Hotel
777 Casino Way Oxford ME
Fully refundableReserve now, pay when you stay
CA $148
CA $161 total
Oct 12 - Oct 13
includes taxes & fees
Jordan Hotel
27 Grand Circle Newry ME
CA $152
CA $186 total
Sep 28 - Sep 29
includes taxes & fees
8.8/10 Excellent! (566 reviews)
"We had a wonderful stay at this hotel. Everything was very clean and well maintained. My kids especially loved the pool area, and the sauna was also very clean and relaxing. The hotel itself is excellent, and we really enjoyed our stay. The only area that could use improvement is the restaurant. ..."
Reviewed on Sep 10, 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.
North Pond
Commune with nature and explore the great outdoors at North Pond during your travels in Woodstock.
Bryant Pond
Commune with nature and explore the great outdoors at Bryant Pond during your travels in Woodstock.
Frequently asked questions
How much does a Woodstock vacation package cost?
You'll find cheap prices on Expedia for your Woodstock escape. However, a range of factors like the length of stay, the season 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'd like to snag a cheap Woodstock vacation package, consider planning a trip in May, September and November. You'll usually find better prices on hotels and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Woodstock?
Usually, a handful of days is enough to tick off the top sights during your Woodstock vacation. But if you prefer to have time to kick back or take day tours, consider extending your itinerary.
How to find the best Woodstock package deals?
Landing a cheap Woodstock package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply a couple of filters and browse what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most affordable Woodstock package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
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 personalize your Woodstock getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Woodstock?
If you've got your Woodstock vacation dates locked in, book early to grab some unbeatable deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Woodstock?
- Choose when to get away: Check your calendar and get packing. Your favourite time of year and the type of activities on offer will also help you decide when to escape to Woodstock.
- Figure out your budget: Make sure you have enough money to pay for everything from food and transportation to activities and flights. Your hotel will likely be the biggest expense during your trip to Woodstock.
- Decide how long to go away for: Now that you're more familiar with Woodstock, you can work out the perfect length of your break. Put together a draft itinerary and give yourself enough time to cover everything you want to see.
- Combine your airfare and accommodations: Once you've settled on your trip dates and duration, lock in the ideal 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.
