Jamaica Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, 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.
Chalet 239

Chalet 239

2 out of 5
Price was CA $1,000, price is now CA $959 per person
CA $959
per person
Aug 27 - Aug 30
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
9.4/10 Exceptional! (129 reviews)
Very clean and cute hotel. Will stay there again.

Reviewed on Jul 1, 2026

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was CA $1,458, price is now CA $1,177 per person
CA $1,177
per person
Aug 27 - Aug 30
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
10/10 Exceptional! (199 reviews)
It was very unique and great

Reviewed on Jul 5, 2026

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,214, price is now CA $1,028 per person
CA $1,028
per person
Aug 27 - Aug 30
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (907 reviews)
I love this place. It's really special. Some people to preserve what was special and exciting and authentic about a historic space and these are my people. They have the amenities you need (great bed and linens, refridgerator, microwave, good towels). They have the amenities you don't need but love! (record players in all rooms and throughout the hotel and vintage vinyl readily available, cucumber water in the lobby, a coffe and tea station in the lobby, a postcard writing station, easy access to a movie theater). This won't be everybodies cup of tea. What used to be luxury amenities are preserved a curiousities, the halls feel like a dorm, and brattleboro is on a downturn. But Brattleboro is also really beauitful, with some lovely restaurants and arts venues. And I love everything about it. If you stay - make sure to stay see a movie. It's gorgeous in there. Turkish breakfast at Tulip in amazing. Shim La's really good. check out the river. Stone Church is a fun venue. And Ther'es a lot to see and love in brattleboro. Also Go to chesterfield and check out madame sherri's castle and the gorge. Enjoy!

Reviewed on Jul 5, 2026

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was CA $1,110, price is now CA $1,015 per person
CA $1,015
per person
Aug 27 - Aug 30
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (278 reviews)
ac had to be turned back on every few hours. fridge broke three times and maintenance needed to bring new ones. pool and hot tub was closed even tho i specifically bought this booking because expedia said it was available. fire pit was nice and they had a great fourth of july celebration

Reviewed on Jul 5, 2026

Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was CA $1,345, price is now CA $1,276 per person
CA $1,276
per person
Sep 5 - Sep 7
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
10/10 Exceptional! (114 reviews)
Holy and Kyle were awesome! Such wonderful breakfasts each day we were there, delicious! So close to everything we wanted to see. We look forward to coming back for our next Vermont getaway!

Reviewed on Jun 19, 2026

Where to stay in Jamaica

Find the best Jamaica areas and neighborhoods for the activities you enjoy most. Learn more about Jamaica
Default Image

Pikes Falls

Though Pikes Falls might not have many top sights, you can venture to the surrounding area to see attractions like Solstice Ski Lift and Sunrise Express Ski Lift.

Find hotels in Pikes Falls

Ready to book your vacation to Jamaica?

 

Choose your dates

Jamaica Hotel Deals

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
Fully refundable
The price is CA $214 per night from Jul 14 to Jul 15
CA $214
CA $256 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (288 reviews)
"ac had to be turned back on every few hours. fridge broke three times and maintenance needed to bring new ones. pool and hot tub was closed even tho i specifically bought this booking because expedia said it was available. fire pit was nice and they had a great fourth of july celebration"

Reviewed on Jul 5, 2026

Grand Summit Resort, A Vail Resorts Property
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
The price is CA $331 per night from Jul 21 to Jul 22
CA $331
CA $423 total
Jul 21 - Jul 22
includes taxes & fees
9.4/10 Exceptional! (854 reviews)
"The hotel was beautiful very tranquil. Lots to see and do. The staff were friendly and attentive to the guests. The food in the restaurant was amazing. The staff there were also friendly. It was so peaceful in the mountains and the hotel grounds were beautiful."

Reviewed on Jun 29, 2026

Kimpton Taconic Hotel by IHG
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Jul 7 to Jul 8
CA $154
CA $169 total
Jul 7 - Jul 8
includes taxes & fees
8.6/10 Excellent! (922 reviews)
"I love this place. It's really special. Some people to preserve what was special and exciting and authentic about a historic space and these are my people. They have the amenities you need (great bed and linens, refridgerator, microwave, good towels). They have the amenities you don't need but love! ..."

Reviewed on Jul 5, 2026

Latchis Hotel
See all 2,618 properties in Jamaica
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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.
See properties

Frequently asked questions

How much does a Jamaica vacation package cost?
You'll find cheap prices from CA $959 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?

  1. Pick your travel dates: What you'd like to do in Jamaica and your preferred season will help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.