Woodstock Vacations from $508

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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.

The Latest Woodstock vacation packages

Price found within the past 48 hours. Click for updated prices.
Silver Creek Resort

Silver Creek Resort

3.5 out of 5
Price was $2,390, price is now $508 per person
$508
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Montego Bay (MBJ)
7/10 Good! (51 reviews)
The only concern we had was that there is no restaurants within walking distance,

Reviewed on May 20, 2024

Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

4.5 out of 5
Price was $3,496, price is now $1,466 per person
$1,466
per person
Mar 14 - Mar 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
9/10 Wonderful! (1,002 reviews)
Clean room, friendly staff, wonderful amenities, and beautiful grounds!

Reviewed on Jan 29, 2026

Ocho Rios Villa at the Palms II

Ocho Rios Villa at the Palms II

3.5 out of 5
Price was $2,038, price is now $965 per person
$965
per person
May 1 - May 7
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
8.6/10 Excellent! (25 reviews)
The property is huge and maybe we were a little unprepared for that but it was a very pleasant experience and I am glad we gave it a crack versus the big names. The host Ms. Powell took excellent care of us and was there from the moment we booked to guide and advise us. Thanks for an amazing stay are your villa.

Reviewed on Apr 25, 2023

Ocho Rios Villa at the Palms III

Ocho Rios Villa at the Palms III

3.5 out of 5
Price was $2,361, price is now $1,123 per person
$1,123
per person
Apr 12 - Apr 19
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
No reviews
Ocho Rios Villa at Coolshade IX

Ocho Rios Villa at Coolshade IX

3.5 out of 5
Price was $2,205, price is now $1,062 per person
$1,062
per person
Apr 12 - Apr 19
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
No reviews
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Woodstock Hotel Deals

Sandals South Coast - ALL INCLUSIVE Couples Only

Sandals South Coast - ALL INCLUSIVE Couples Only

4.5 out of 5
A2 Whitehouse Westmoreland
8.6/10 Excellent! (140 reviews)
Got attacked by bed bugs! Room was not very clean. Didn’t have a working tv for 3 days. The staff wasnt very friendly. Unless you were a priority guest, you weren’t really treated the same. Booked a luxury resort for our anniversary and we’re expecting it to be better. The resort itself was beautiful ...

Reviewed on Sep 7, 2025

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Sandals South Coast - ALL INCLUSIVE Couples Only
Villa Serene Jewel of Black River 4 bedroom 5bathrooms

Villa Serene Jewel of Black River 4 bedroom 5bathrooms

Black River St. Elizabeth
9.4/10 Exceptional! (11 reviews)
Amazing!!!
The pictures do not give this Villa justice, it is beautiful! We had an amazing time there! We were looking for rest and relaxation and that is exactly what we got!! Shamoir the cook was incredible! Sheryl was quick to respond to any questions we had! We will definitely go back!

Reviewed on Feb 26, 2023

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Villa Serene Jewel of Black River 4 bedroom 5bathrooms
10BR Luxury Villa w/ Private Beach , Fully Staffed w/ Chef - STSHA

10BR Luxury Villa w/ Private Beach , Fully Staffed w/ Chef - STSHA

Sandy Ground Westmoreland Parish
10/10 Exceptional! (1 review)
Relaxing Getaway
Perfect for our team of 18! Everyone enjoyed the food, the staff, the ambience. It was great to have our own privacy to bond as a team. Everything was immaculate! Minor problems- The internet connectivity was slow or didn't work, and the power tripped out 1-2 times per day, however, speedily restored ...

Reviewed on Jan 16, 2024

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10BR Luxury Villa w/ Private Beach , Fully Staffed w/ Chef - STSHA
See all 195 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.

Find the Best Woodstock Vacation Packages

Woodstock Essential Information

Language
English
Currency
Jamaican dollars
Closest Airport
Sir Donald Sangster Intl. Airport (MBJ)
Top Sights
YS Falls, Appleton Estate and Bubbling Spring Mineral Bath

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Frequently asked questions

How much does a Woodstock vacation package cost?
You'll find cheap prices from $508 on Expedia for your Woodstock break. However, 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?
You're likely to find lower prices and better availability in July, November and December. Check out our cheap Woodstock vacation packages and you could score some great off-season deals.
How many days is enough for Woodstock?
The ideal length for your Woodstock vacation depends on what you'd like to see and do. Generally, a few days to a week will give you time to hit all the leading attractions and discover some hidden treasures along the way.
How to find the best Woodstock package deals?
Bagging a cheap Woodstock package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most pocket-friendly 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 generally lower.
Is it cheaper to book a Woodstock vacation as a package?
You can enjoy significant savings on your Woodstock escape by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to view the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Woodstock?
If you've got your Woodstock travel dates confirmed, book early to bag some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Woodstock?

  1. Choose when to get away: Check your diary and pack your bags. Your favorite season and the available activities will also help you decide when to visit Woodstock.
  2. Set a budget: Factor in expenses such as flights, food and transportation when calculating how much to put aside for your trip to Woodstock. Then, pick a hotel that matches your budget, whether that's a wallet-friendly option or a high-end getaway.
  3. Explore Woodstock with Expedia's trip planning tool: Gain insights into the most popular attractions and best stays for your trip to Woodstock. You can also save your favorite places, collaborate with friends and family and organize all your plans in one place.
  4. Decide how long to go for: Now that you're up to speed on Woodstock, you can figure out the perfect length of your vacation. Create a rough itinerary and allocate enough time to cover everything you want to do.
  5. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a customized Woodstock vacation package.
  6. Add on experiences and excursions: Have a look at our travel guide to find some fun things to do in Woodstock. Book tickets or make reservations before you go to save time and avoid the hassle of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Woodstock vacation packages?
Your Woodstock trip should be a relaxing escape from your busy life, not a reason for money worries. So to allow you that extra flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.