Jamaica Vacation Packages

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Your Jamaica Vacation

Book a customized Jamaica vacation package that includes only the things you need and nothing you don't. Good for views, families and nature, consider basing yourself in the neighborhood of Bromley Mountain. A trip to Jamaica is a wonderful opportunity to do a bit of sightseeing. Be sure to visit big-name attractions such as Jamaica State Park, Stratton Mountain Golf Course and Winhall River. A couple of quick clicks is all it takes to put together your dream Jamaica vacation on Expedia.

Top Jamaica Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
Clock Tower Base Area
Price was CA $2,352, price is now CA $2,187 per person
CA $2,187
per person
Oct 8 - Oct 13
found 20 hours ago
Roundtrip flight included
Ottawa (YOW) to Springfield (VSF)
8/10 Very Good! (207 reviews)
Loved the location for this ski in ski out. Nice to look out the balcony and be right in the middle of the action. The sofa bed was uncomfortable with springs popping up all over. The back door didn't lock and the window handle was broken . There was a light bulb that was out and not all the outlets worked. The tv situation was a nightmare with one tv all snowy and the other one whose remote was missing the select button and could not choose a channel. The location was great but would not choose this room again .

Reviewed on Feb. 19, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $4,943, price is now CA $3,824 per person
CA $3,824
per person
Oct 8 - Oct 13
found 20 hours ago
Roundtrip flight included
Ottawa (YOW) to Springfield (VSF)
8.8/10 Excellent! (806 reviews)
This is a perfect family oriented spot for visiting downtown Woodstock. We stayed in one of their family suites. It was spacious and comfortable without being ostentatious. Loved the details in the outdoor space--well tended plants and flowers, as well as, fire pits and Adirondack chairs to hang out by the river.

Reviewed on Aug. 18, 2025

Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
Price was CA $2,630, price is now CA $2,393 per person
CA $2,393
per person
Oct 8 - Oct 13
found 20 hours ago
Roundtrip flight included
Ottawa (YOW) to Springfield (VSF)
8.8/10 Excellent! (23 reviews)
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
Price was CA $2,492, price is now CA $2,291 per person
CA $2,291
per person
Oct 8 - Oct 13
found 20 hours ago
Roundtrip flight included
Ottawa (YOW) to Springfield (VSF)
8/10 Very Good! (26 reviews)
Very friendly costumer service, we arrived late and we're greated with kindness.

Reviewed on Sep. 16, 2024

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was CA $2,461, price is now CA $2,267 per person
CA $2,267
per person
Oct 8 - Oct 13
found 20 hours ago
Roundtrip flight included
Ottawa (YOW) to Springfield (VSF)
8.6/10 Excellent! (751 reviews)
Electric car chargers are not in the buildings anymore. Inconvenient.

Reviewed on Aug. 21, 2025

Ready to book your vacation to Jamaica?

 

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Jamaica Hotel Deals

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Sep 3 to Sep 4
CA $193
CA $288 total
Sep 3 - Sep 4
includes taxes & fees
7.2/10 Good! (515 reviews)
"When we arrived the front desk had 2 people working with numerous check ins as there was a convention checking in as well as other guests. They were understaffed in many departments. The elevator rug needed replacement as it was dirty and worn. The side entrances were full of large spider webs and ..."

Reviewed on Aug. 21, 2025

The Equinox Golf Resort & Spa
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Aug 27 to Aug 28
CA $194
CA $213 total
Aug 27 - Aug 28
includes taxes & fees
6.6/10 (1,003 reviews)
"Appears to house a lot of homeless."

Reviewed on Aug. 22, 2025

Colonial Motel And Spa
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St., Manchester, VT
Fully refundable
The price is CA $254 per night from Sep 7 to Sep 8
CA $254
CA $332 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (794 reviews)
"Very nice property with friendly staff; excellent food at the restaurant; was only there for 16 hours but definitely want to go back to stay longer."

Reviewed on Aug. 20, 2025

Kimpton Taconic Hotel by IHG
See all 2,473 properties in Jamaica
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.
All Inclusive Vacations
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Discover the most popular places to visit in Jamaica

Jamaica State Park

You can take time to visit Jamaica State Park during your travels to Jamaica. Amble around the area's parks or visit its monuments.

Jamaica State Park

Margie's Muse Handweaving & Gallery

You can spend an afternoon browsing the exhibits at Margie's Muse Handweaving & Gallery in Jamaica. Discover the mountain views in this quaint area, or enjoy its ski slopes.

Margie's Muse Handweaving & Gallery

Frequently asked questions

How much does a Jamaica vacation package cost?
You'll find cheap prices from CA $2,187 on Expedia for your Jamaica getaway. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Jamaica costs.
What are the cheapest months to go to Jamaica?
Plan your trip for the low season and you're likely to get cheap Jamaica vacation packages. Remember that public holidays and major festivals and events can have an impact on prices, so do your research before booking.
How many days is enough for Jamaica?
Jamaica vacations come in many shapes and sizes, but to get a true feel for this place, we'd suggest 3 days is a good ballpark. This will mean you can fit in top attractions like Stratton Mountain Golf Course and Townshend State Park and track down some underrated spots. Don't skip cool areas such as Rawsonville and Forest Farms either. If you plan wisely, you may even be able to take a day trip outside of Jamaica too.
How to find the best Jamaica package deals?
Use Expedia's handy filters to find some of the best Jamaica package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Jamaica package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Jamaica vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Jamaica vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Jamaica?
If you've got your Jamaica vacation dates confirmed, book as soon as you can to grab some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Jamaica?

  1. Pick your travel dates: What you'd like to do in Jamaica and your preferred season will help you decide when to travel.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and dining out to activities and flights. Your accommodations will likely be the biggest expense during your trip to Jamaica.
  3. Decide how many days away: Start by listing all the sights and activities you'd like to experience in Jamaica. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Jamaica vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.