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.
Sinclair Inn Bed and Breakfast
CA $1,653
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Springfield (VSF)
10/10 Exceptional! (119 reviews)
Everything about Sinclair Inn Bed and Breakfast was exceptional. Holly and Kyle were welcoming hosts the property is very well maintained and the gardens are beautiful with areas to sit and relax. Breakfast was delicious with a variety of options with fresh berries, yogurt and granola to build your own parfait, delicious quiche, fresh baked goods. And delicious cookies for Night time snack.
I would highly recommend this establishment for your next trip to the area.
Reviewed on Aug 10, 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 Tamarack 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 Tamarack 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
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
Fully refundable
CA $305
CA $394 total
Sep 9 - Sep 10
includes taxes & fees
9.4/10 Exceptional! (860 reviews)
"Excellent amenities and perfect if you're traveling with a dog to VT. Rooms are very nice albeit a bit small and very low water pressure in the shower."
Reviewed on Aug 3, 2026
The Equinox Golf Resort & Spa
3567 Main Street Route 7A Manchester VT
Fully refundableReserve now, pay when you stay
CA $185
CA $279 total
Aug 24 - Aug 25
includes taxes & fees
7.4/10 Good! (658 reviews)
"Our requested room that was done at time of online reservation was changed due to room needing maintenance we were told. The room we were sent to was needing some attention. Shattered pain glass on interior window and wallpaper peeling down on bathroom wall and ceiling paint coming down on bathroom. ..."
Reviewed on Aug 13, 2026
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
CA $129
CA $142 total
Aug 20 - Aug 21
includes taxes & fees
8.6/10 Excellent! (952 reviews)
"BAD, Did not stay after seeing the room. No refund."
Reviewed on Aug 12, 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 $1,653 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.
