Jamaica 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 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
CA $1,231
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
6.8/10 (46 reviews)
The room was dirty and smelled musty and of urine. The hallways have all broken down ice machines and the breakfast was non-existent.
Reviewed on Sep 6, 2026
Hideaway Inn Mt. Snow
CA $1,463
per person
Oct 10 - Oct 13
found 5 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
8.6/10 Excellent! (128 reviews)
This was the perfect long weekend get away. The property was fairly quiet given it was the off season. Phone check-in and check-out was lovely, and if you don’t enjoy standard hotel check-in lines, it’s even better. The pool and hot tub were beautiful, and while we didn’t use them, they were very clean. It is a very pet friendly place, but doesn’t smell of animals, and there’s no sign of them (unless you meet one in the hallway). The always available hot chocolate and coffee machine was AMAZING! Highly recommend the hot chocolate.
We only saw the cleaner once in passing (they don’t go in your room while you’re there), and she was so nice! There’s also extra supplies for you in the main hall closet should you need them (extra towels, tooth brushes, etc.).
It truly felt like a home away from home. The only “downside” is that the walls are a bit thin so you can kind of hear what your neighbors are doing if they’re being rowdy, but that’s more managing personal volume levels.
10/10, we’ll definitely stay again!
Reviewed on Sep 8, 2026
Mount Snow Lodging by Vail Resorts
CA $1,753
per person
Oct 10 - Oct 13
found 5 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
7.8/10 Good! (23 reviews)
The bar tender in the lounge on Saturday 10/18 was not friendly. Seemed like he didn’t like his job. He was the only one working and there were not many customers at the bar. Dining room had no one in it. He just was not attentive to me party of 3 who just wanted to order a drink. Fitness center at the Season was very nice but hours were not very accommodating
Reviewed on Oct 20, 2025
Latchis Hotel
CA $1,279
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
8.6/10 Excellent! (974 reviews)
Considering the age of the property, this is a great stay! The staff was super helpful upon arrival, helping with check-in, parking and directions. The proximity to shops and restaurants is amazing. The room was clean and comfortable. I love that there were extra fans in the room to account for the lack of AC. Definitely still stay again!
Reviewed on Sep 5, 2026
Mountain Lodge at Okemo, A Vail Resorts Property
Clock Tower Base Area
CA $1,441
per person
Oct 10 - Oct 13
found 5 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
8/10 Very good! (225 reviews)
Staff was very helpful, the property is very clean, the room was clean with lots of space. The kitchen had a full size refrigerator and microwave. I was very happy overall
Reviewed on Jul 19, 2026
Where to stay in Jamaica
Find the best Jamaica areas and neighborhoods for the activities you enjoy most. Learn more about Jamaica
Pikes Falls
Though Pikes Falls might not have many top sights, you can venture to the surrounding area to see attractions like Sunrise Express Ski Lift and Solstice Ski Lift.
Mountain Acres
Though Mountain Acres might not have many top sights, you can venture to the surrounding area to see attractions like Jamaica State Park and Sunrise Express Ski Lift.
East Jamaica
While visiting East Jamaica, you might make a stop by sights like Green Mountain National Forest and West River.
Ready to book your vacation to Jamaica?
Jamaica Hotel Deals
Latchis Hotel
50 Main Street Brattleboro VT
CA $150
CA $165 total
Sep 10 - Sep 11
includes taxes & fees
8.6/10 Excellent! (976 reviews)
"Considering the age of the property, this is a great stay! The staff was super helpful upon arrival, helping with check-in, parking and directions. The proximity to shops and restaurants is amazing. The room was clean and comfortable. I love that there were extra fans in the room to account for the ..."
Reviewed on Sep 5, 2026
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
CA $215
CA $258 total
Sep 22 - Sep 23
includes taxes & fees
8.6/10 Excellent! (308 reviews)
"Pool and hot tub were closed, no fresh towels or maid service or coffee replenishment. No shuttle service available and no coffee cups provided in the lobby for complimentary coffee. The bar closed at 8:30 even though posted hours were until 10:00"
Reviewed on Sep 7, 2026
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
CA $115
CA $126 total
Sep 10 - Sep 11
includes taxes & fees
6.6/10 (54 reviews)
"The room was dirty and smelled musty and of urine. The hallways have all broken down ice machines and the breakfast was non-existent."
Reviewed on Sep 6, 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.
Stay near popular Jamaica attractions
Jamaica State Park
8.8/10 (5 reviews)
You can take time to visit Jamaica State Park during your travels to Jamaica. Amble around the area's parks or visit its monuments.
Ball Mountain Dam
Learn about the local history of Jamaica when you take a trip to Ball Mountain Dam. Discover the mountain views in this quaint area, or enjoy its ski slopes.
Hot Glass Works
You can spend an afternoon exploring the galleries in Hot Glass Works during your trip to Jamaica. Discover the mountain views in this quaint area, or enjoy its ski slopes.
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.
Ball Mountain State Park
Enjoy a trip to Ball Mountain State Park and popular activities like skiing in Jamaica. Discover the mountain views in this quaint area.
Frequently asked questions
How much does a Jamaica vacation package cost?
You'll find cheap prices from CA $1,231 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?
- Pick your travel dates: What you'd like to do in Jamaica and your preferred season will help you decide when to travel.
- 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.
- 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.
- 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.
