Woodstock Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Your Woodstock Vacation
Organizing your next escape is a walk in the park with a Woodstock vacation package. The neighborhood of New Hope, which is great for walking, makes a good launchpad to discover the treasures of this unique city. Eager to do a bit of sightseeing? A trip to Woodstock wouldn't be complete without visiting YS Falls, Bubbling Spring Mineral Bath and other big-name attractions. Whatever your travel plans or budget, organizing a tailored Woodstock vacation is a breeze with Expedia.
Top Woodstock Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ocho Rios Villa at The Palms
CA $1,451
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
All staff were professional, courteous and friendly. They all went out of their way to grant your requests. The ambience is very nice. The electrical outlets on the patio didn't always work. Had to be creative in getting plugs to stay in. They also need to upgrade from 110v to 220v. Just kidding, but they should have something for travelers from Europe. Internet service was pretty good. Everyone in my group were pleased and would return. The tour setup for us by the manager was fun!!!! Good people, fantastic accommodations. Recommended...
Reviewed on May 8, 2019
Ocho Rios Villa at Coolshade
CA $1,496
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
9.8/10 Exceptional! (10 reviews)
Clean house with ac in each room very cozy and private area great security and safe environment. Love the grocery store across the street good food. You would need to have a vehicle to enjoy it like I did, i rented a Kia. Nice pool and gym has new equipment being installed 👍
Reviewed on Jun 6, 2026
Retreat Plantation House
CA $1,517
per person
Nov 26 - Dec 3
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
10/10 Exceptional! (1 review)
Totally enjoyed our stay at Retreat Plantation, home away from home , excellent management, Robin and his housekeepers we're L extremely pleasant. We would definitely go again!
Reviewed on Feb 17, 2017
Ready to book your vacation to Woodstock?
Woodstock Hotel Deals
Sandals South Coast - ALL INCLUSIVE Adults Only
A2 Whitehouse Westmoreland
8.6/10 Excellent! (142 reviews)
"Very dangerous and delayed the trip from the airport to the hotel"
Reviewed on Oct 27, 2025
Idlers' Rest Beach Hotel
Parottee Road, A2 Black River Saint Elizabeth
7.6/10 Good! (89 reviews)
"Beautiful beach location"
Reviewed on Jul 8, 2024
Indigo Beach Villa - Black River
79 Crane Road Black River St. Elizabeth Parish
CA $107
CA $124 total
Sep 6 - Sep 7
includes taxes & fees
6.8/10 (16 reviews)
"This property does not exist as a rental. It should NOT be available to book. I lost about $300.00 for this place. IT IS A SCAM!!!"
Reviewed on Jul 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.
Frequently asked questions
How much does a Woodstock vacation package cost?
Live it up in Woodstock from as little as CA $1,451. Choose from a great selection of flights, rental cars and hotels to suit every budget. Score even better deals when you add a couple of experiences or tours to your package.
How do I get a cheap travel package to Woodstock?
Combine your bookings with Expedia to save big bucks on your next trip. With more than 550 partner airlines and 1,000,000 properties around the globe, your Woodstock vacation package can be customized exactly to suit your budget. With all those extra dollars, why not add one or more interesting tours and activities? It's an easy way to unlock even more bargains. Your dream vacation in Woodstock is much closer than you thought!
How far in advance should I book my Woodstock vacation?
While prices change frequently, we generally suggest booking your flight as soon as possible. Many international fares can be found on Expedia up to a year in advance. If you're booking late, you might still get lucky. Cheap journeys to Woodstock sometimes occur only weeks before departure.
What does an Expedia Woodstock travel package include?
Select from a combination of flights, hotels and rental cars. Once you've made your booking, you can also add on tours and activities. Want to pick your airfare class? That's possible too. The choice is all yours when it comes to organizing your perfect Woodstock trip.
What should I know before booking a Woodstock travel package?
You can save big by combining your airfares, hotels and rental cars. Once you've made your booking, add on fun stuff like activities or tours. Your next awesome vacation is only a couple of clicks away.
Can I choose my airline with a Woodstock Expedia vacation package?
Yes, the choice is all yours. We offer more than 550 partner airlines all over the world, so you can customize your Woodstock vacation according to your needs and budget.
If I'm not able to travel, can I cancel my Woodstock vacation package?
It's difficult to predict what the future holds, so it's comforting to know that you can change or cancel your Woodstock vacation package. If your booking was made in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal to learn more.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
