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.
Comfort Inn & Suites Brattleboro I-91
CA $1,133
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (852 reviews)
The room was nice and clean. The air-conditioning was great. We love that there was a restaurant about 200 feet away. That was actually pretty good. The young man who checked us in was very friendly.
Reviewed on Sep 16, 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 Villager 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 Villager 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
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
CA $218
CA $261 total
Oct 18 - Oct 19
includes taxes & fees
8.6/10 Excellent! (309 reviews)
"Very clean. Staff were super helpful. Beautiful even though it was “off-season”."
Reviewed on Sep 15, 2026
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
CA $116
CA $127 total
Sep 20 - Sep 21
includes taxes & fees
6.6/10 (58 reviews)
"Horrible place."
Reviewed on Sep 16, 2026
The Manchester View
77 High Meadow Way & VT-7A Manchester Center VT
Fully refundableReserve now, pay when you stay
CA $150
CA $165 total
Sep 21 - Sep 22
includes taxes & fees
9.4/10 Exceptional! (896 reviews)
"Great place. Exceeded our expectations. The view, and surroundings are spectacular. And the "continental" breakfast was beyond continental. And it's dog friendly!!!"
Reviewed on Sep 15, 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.
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.
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.
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 $1,032 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.
