Woodstock Vacations from $928

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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.
Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
Price was $2,108, price is now $928 per person
$928
per person
Feb 10 - Feb 15
found 1 day ago
Roundtrip flight included
New York (JFK) to Montego Bay (MBJ)
20/10 Exceptional! (2 reviews)
Alamanda Cottage at Serenity

Alamanda Cottage at Serenity

3 out of 5
Ironshore
Price was $3,238, price is now $1,149 per person
$1,149
per person
Jan 3 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
No reviews
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 $5,808, price is now $2,122 per person
$2,122
per person
Feb 12 - Feb 19
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
18/10 Exceptional! (1,002 reviews)
Very nice small resort, very quiet, staff is very pleasant, rooms are clean and roomy, beach is private and beautiful. We had a very relaxing holiday while here.

Reviewed on Nov 19, 2025

Retreat Plantation House

Retreat Plantation House

3 out of 5
Save 100% on your flight
Price was $1,960, price is now $963 per person
$963
per person
Jan 5 - Jan 11
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
20/10 Exceptional! (1 review)
Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Price was $3,487, price is now $1,714 per person
$1,714
per person
Jan 27 - Feb 2
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
17.2/10 Exceptional! (5,147 reviews)
The staff was very polite abd courteous. Entertainment was on another level. Love it

Reviewed on Nov 16, 2025

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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)
The staff were friendly and very accommodating.

Reviewed on Dec 31, 2024

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Sandals South Coast - ALL INCLUSIVE Couples Only
Idlers' Rest Beach Hotel

Idlers' Rest Beach Hotel

3 out of 5
Parottee Road, A2 Black River Saint Elizabeth
Beautiful beach location

Reviewed on Jul 8, 2024

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Idlers' Rest Beach Hotel
Indigo Beach Villa - Black River

Indigo Beach Villa - Black River

3 out of 5
79 Crane Road Black River St. Elizabeth Parish
$126 nightly
The price is $146 total per night from Nov 23 to Nov 24
$146 total
Nov 23 - Nov 24
Total with taxes and fees
7.2/10 Good! (12 reviews)
My family and I had a wonderful stay at this property. Great location in Black River on the beach. The place was easy to find, safe, and clean. The beds were very comfy, cool AC, and had great wifi. I highly recommend staying here and will stay again in the future.

Reviewed on Apr 21, 2025

Indigo Beach Villa - Black River
See all 203 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 $928 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.