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.
Vikings Villages Resort
CA $1,580
per person
Jan 2 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Springfield (VSF)
10/10 Exceptional! (240 reviews)
Nice and quiet space, secluded in the woods with the cabins in a row. Very well done architecture and decorations.
Reviewed on Oct 5, 2026
The Shire Woodstock
CA $1,482
per person
Jan 2 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Springfield (VSF)
8.8/10 Excellent! (994 reviews)
I booked this at the last minute and knew I was paying more because of the autumn season. Even so, the stay was not worth the price.
The bed creaked very loudly every time I moved, and the mattress dipped badly in the middle. I could also hear street noise throughout the night.
Overall, this felt more like a 2* star motel than a hotel charging this price. A very disappointing and unrestful stay.
Reviewed on Oct 6, 2026
Sinclair Inn Bed and Breakfast
CA $1,480
per person
Jan 2 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Springfield (VSF)
10/10 Exceptional! (127 reviews)
Friendly owners and the property was amazing Beautiful garden, even in the fall Breakfast was delicious
Reviewed on Sep 25, 2026
1846 Inn and Tavern
CA $1,552
per person
Jan 2 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Springfield (VSF)
10/10 Exceptional! (1 review)
We went for a girls trip for one night! Everything was amazing from check in to check out! We felt like we were greeting and taking care of our stay. The food is amazing the atmosphere is fantastic and can’t wait till next year!!!!
Reviewed on Sep 21, 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
Aspen At Manchester
5669 Main Street Manchester Center VT
CA $147
CA $177 total
Nov 2 - Nov 3
includes taxes & fees
8.8/10 Excellent! (699 reviews)
"Great place, but a bit over priced for what it is"
Reviewed on Oct 5, 2026
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
CA $119
CA $130 total
Nov 1 - Nov 2
includes taxes & fees
6.4/10 (79 reviews)
"This place is tired. Not many options in the area. Not my first time here. New ownership, but it doesn't look or feel any different. Plumbing back ups in sink and tub. Moved the trashcan and there was trash and dirt behind it. Stain on comforter. You know, tired."
Reviewed on Oct 5, 2026
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
CA $218
CA $261 total
Nov 4 - Nov 5
includes taxes & fees
8.6/10 Excellent! (313 reviews)
"1"
Reviewed on Oct 5, 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 $1,408 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.
