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.
Colonial Motel
CA $1,025
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
6.6/10 (61 reviews)
I’ve stayed in over 30 hotels this year and this was the most disgusting place. Carpet was sticky, old with iron burn marks. Mold on shower curtain and in tub. Hair in tub. No shampoo or conditioner. Blow dryer almost caught fire. AC thermostat was not working. It was either really cold or hot. I would never stay there again.
Reviewed on Oct 2, 2026
Latchis Hotel
CA $1,118
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (989 reviews)
We arrived late in the afternoon and were given the keys to our hotel room. When we got to the room it smelled like smoke. We opened the window to try and get the smell out. When my wife went into the bathroom there was still a used towel hanging. At that point we decided to leave. The staff was very understanding and helpful with this request and we did get a complete refund.
Reviewed on Oct 2, 2026
Hampton Inn Brattleboro
CA $1,088
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.2/10 Very good! (1,008 reviews)
We stay here 2 or 3 times a year and know it well. The staff are always welcoming and helpful. On this visit, we found our original room to be noisy because of the ice machine (?), but the staff got us another room when asked.
The room was spacious, quiet and comfortable.
The hotel was unusually full, but very quiet. Breakfast is always good here and the coffee is excellent. (Vermont seems to be obsessed with coffee....)
Having tried two or three other hotels in Brattleboro, we have settled on the Hampton Inn as our "go to" spot.
Reviewed on Oct 3, 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
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
CA $118
CA $130 total
Nov 1 - Nov 2
includes taxes & fees
6.6/10 (72 reviews)
"I’ve stayed in over 30 hotels this year and this was the most disgusting place. Carpet was sticky, old with iron burn marks. Mold on shower curtain and in tub. Hair in tub. No shampoo or conditioner. Blow dryer almost caught fire. AC thermostat was not working. It was either really cold or hot. I ..."
Reviewed on Oct 2, 2026
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
CA $213
CA $255 total
Nov 2 - Nov 3
includes taxes & fees
8.6/10 Excellent! (312 reviews)
"What I like is the room was well stocked, very clean and the staff is very helpful. What I did not like is the parking is very inconvenient and is quite a walk which is never fun in bad weather. They need more luggage carts. It looked like they have about 5 or 6 for about a 200 room hotel. There ..."
Reviewed on Sep 27, 2026
Aspen At Manchester
5669 Main Street Manchester Center VT
Fully refundableReserve now, pay when you stay
CA $147
CA $177 total
Nov 2 - Nov 3
includes taxes & fees
8.8/10 Excellent! (698 reviews)
"This could be a great place to stay, but the property managers need to invest more in the customer experience. Check in after 4 pm is more challenging than it should be. If you book the room online, the on duty rep is NOT notified (despite their “fully automated” system). You have to call the number, ..."
Reviewed on Oct 2, 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.
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.
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.
Frequently asked questions
How much does a Jamaica vacation package cost?
You'll find cheap prices from CA $1,025 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.
