Woodstock Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Top hotels in Woodstock
Grand Summit Hotel
97 Summit Road Newry ME
S$178
29 Sept - 30 Sept
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 8 Sept, 2026
Oxford Casino Hotel
777 Casino Way Oxford ME
Fully refundableReserve now, pay when you stay
S$146
12 Oct - 13 Oct
includes taxes & fees
Jordan Hotel
27 Grand Circle Newry ME
S$170
28 Sept - 29 Sept
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
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 holiday 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 holiday to Woodstock costs.
What are the cheapest months to go to Woodstock?
If you're hoping to book a cheap Woodstock holiday 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 holiday. 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 holiday package as soon as possible.
Is it cheaper to book a Woodstock holiday as a package?
An Expedia holiday 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 holiday 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 holiday.
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 accommodation and airfare: Once you've settled on your travel dates and duration, lock in the right Woodstock holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
