Woodstock Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Woodstock Vacation Packages

Woodstock Hotel Deals

Oxford Casino Hotel

Oxford Casino Hotel

3 out of 5
777 Casino Way, Oxford, ME
Fully refundableReserve now, pay when you stay
The price is ₩185,538 per night from Sep 14 to Sep 15
₩185,538
₩202,237 total
Sep 14 - Sep 15
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"It was quite and friendly. only thing is in my hurry to check out I left my dress over the chair by the desk. It is cream with pink flowers. I left a message with housekeeping with my phone #, and room # 310 on 8/15/2025. I have not heard from anyone. But still I would stay again."

Reviewed on Aug 22, 2025

Oxford Casino Hotel
Evergreen Valley Inn

Evergreen Valley Inn

3 out of 5
82 Mountain Road, Stoneham, ME
The price is ₩174,829 per night from Aug 26 to Aug 27
₩174,829
₩190,563 total
Aug 26 - Aug 27
includes taxes & fees
8/10 Very Good! (166 reviews)
"Definitely make arrangements for food before arrival, whether grocery shopping or take out. This beautiful Inn is nestled far away from hustle and noise. All you are surrounded by is nature and beauty. Rooms are a bit dusty but comfortable. The staff are very accommodating and kind. We enjoyed our ..."

Reviewed on Aug 23, 2025

Evergreen Valley Inn
Jordan Hotel

Jordan Hotel

3 out of 5
27 Grand Circle, Newry, ME
The price is ₩193,701 per night from Aug 26 to Aug 27
₩193,701
₩235,942 total
Aug 26 - Aug 27
includes taxes & fees
8.6/10 Excellent! (389 reviews)
"An amazing place with gorgeous views. Staff was very helpful and nice. Thoughtful details all around the hotel. A lot of fun activitys for kids and adults. Unforgettable hiking paths that start from the territory of the hotel and a relaxing heated pool. We we're amazed by the evening mocktails provided ..."

Reviewed on Aug 19, 2025

Jordan Hotel
See all 1,072 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.

Discover the most popular places to visit in Woodstock

Shagg Pond

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.

Shagg Pond

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.