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.
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was CA $1,141, price is now CA $1,050 per person
CA $1,050
per person
Aug 14 - Aug 17
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
8.6/10 Excellent! (284 reviews)
We were very disappointed upon arrival to hear that the pool was closed for the summer. It was 4th of July weekend and we were traveling with grandkids. We would not have booked there if we had known.

Reviewed on Jul 10, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $2,961, price is now CA $2,067 per person
CA $2,067
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Springfield (VSF)
8.8/10 Excellent! (954 reviews)
Absolutely beautiful setting! The room was better than expected-- spacious, clean and gorgeously decorated. The location was also great-- everything was walkable. Highly recommend.

Reviewed on Jul 5, 2026

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was CA $1,442, price is now CA $1,063 per person
CA $1,063
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Springfield (VSF)
8.6/10 Excellent! (862 reviews)
great location but dated

Reviewed on Jul 10, 2026

Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was CA $1,756, price is now CA $1,515 per person
CA $1,515
per person
Aug 15 - Aug 21
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) 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

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,419, price is now CA $1,246 per person
CA $1,246
per person
Aug 14 - Aug 17
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
8.6/10 Excellent! (915 reviews)
We loved our stay at the Latchis! A gem, with great staff and unique character! Can't wait to return!

Reviewed on Jul 10, 2026

Where to stay in Jamaica

Find the best Jamaica areas and neighborhoods for the activities you enjoy most. Learn more about Jamaica
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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 Stratton Mountain Resort.

Find hotels in Pikes Falls

Ready to book your vacation to Jamaica?

 

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Jamaica Hotel Deals

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 $336 per night from Jul 27 to Jul 28
CA $336
CA $428 total
Jul 27 - Jul 28
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
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 $212 per night from Aug 10 to Aug 11
CA $212
CA $254 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (290 reviews)
"We were very disappointed upon arrival to hear that the pool was closed for the summer. It was 4th of July weekend and we were traveling with grandkids. We would not have booked there if we had known."

Reviewed on Jul 10, 2026

Grand Summit Resort, A Vail Resorts Property
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 $172 per night from Jul 12 to Jul 13
CA $172
CA $190 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (926 reviews)
"We loved our stay at the Latchis! A gem, with great staff and unique character! Can't wait to return!"

Reviewed on Jul 10, 2026

Latchis Hotel
See all 2,611 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.
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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 $1,050 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.