Jamaica Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
6.8/10 (1,001 reviews)
Not well maintained but the room was large

Reviewed on Jul. 9, 2025

Mountaineer Inn

Mountaineer Inn

2 out of 5
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.8/10 Excellent! (472 reviews)
It was ok for the price. I could hear the people walking around above me but that stopped by bedtime. The room didn’t have a refrigerator so I went to the community refrigerator but it was tiny. There were no towels in the bathroom but an automated text directed me where to find them in the hall. The volume on the tv wouldn’t go beyond 14 so it was difficult to hear, especially with the air conditioner on. The pool was not functioning and I had left my activity early so I could go for a swim. The shower was pretty good and the bed was comfortable.

Reviewed on Jul. 6, 2025

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (194 reviews)
Great property for family vacations during summer. Will return.

Reviewed on Jul. 6, 2025

Black Mountain Inn

Black Mountain Inn

2 out of 5
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
7.4/10 Good! (439 reviews)
Staff was lovely and room was clean. Also enjoyed a nice bath in the tub after my legs hurt from hiking and swinning, Great stay for the price and close to then wonderful nature of Brattleboro. Would definitely stay again.

Reviewed on Jul. 8, 2025

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (644 reviews)
Beds were comfortable and Desk attendant was very nice

Reviewed on Jun. 16, 2025

Ready to book your vacation to Jamaica?

 

Choose your dates

Jamaica Hotel Deals

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 $134 per night from Aug 12 to Aug 13
CA $134
CA $147 total
Aug 12 - Aug 13
includes taxes & fees
6.6/10 (1,004 reviews)
"This is my go to place to stay. Its always clean, check in is quick and easy. The staff has always been polite and helpful when something has come up. The price is the best around."

Reviewed on Jul. 8, 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 $240 per night from Jul 15 to Jul 16
CA $240
CA $317 total
Jul 15 - Jul 16
includes taxes & fees
9.2/10 Wonderful! (776 reviews)
"Our favorite place to stay in the area"

Reviewed on Jun. 20, 2025

Kimpton Taconic Hotel by IHG
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 $192 per night from Jul 27 to Jul 28
CA $192
CA $286 total
Jul 27 - Jul 28
includes taxes & fees
7.2/10 Good! (492 reviews)
"Just love the very historic sence"

Reviewed on Jul. 6, 2025

The Equinox Golf Resort & Spa
See all 2,494 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

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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 $855 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.