Woodstock Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Woodstock

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 S$200 per night from 8 Sept to 9 Sept
S$200
8 Sept - 9 Sept
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Great price great property"

Reviewed on 13 Aug, 2025

Oxford Casino Hotel
Jordan Hotel

Jordan Hotel

3 out of 5
27 Grand Circle, Newry, ME
The price is S$224 per night from 7 Sept to 8 Sept
S$224
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (385 reviews)
"We had everything we needed. We were very comfortable."

Reviewed on 13 Aug, 2025

Jordan Hotel
Grand Summit Hotel

Grand Summit Hotel

3 out of 5
97 Summit Road, Newry, ME
8.2/10 Very Good! (274 reviews)
"This is located in a ski- area and i was here in the off season. The hotel was conveniently located to several local pubs and restaurants. Family friendly but quiet i would visit again"

Reviewed on 17 Aug, 2025

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Grand Summit Hotel
See all 1,069 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.

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?

  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 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.