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.
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 $1,502, price is now CA $1,264 per person
CA $1,264
per person
Sep 9 - Sep 14
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (858 reviews)
Property beautiful. Rooms very large. Staff very friendly. The only thing that was odd to me was none of our closets had rods to hang clothes on. We were going to a formal wedding, my husband had a suit and I had a long dress to hang up, but the closets had no rods, and we had 3 closets in our room. Had to hang the suit from a door handle and the long dress from the shower rod!

Reviewed on Jun 28, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $2,698, price is now CA $2,097 per person
CA $2,097
per person
Sep 9 - Sep 14
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8.8/10 Excellent! (935 reviews)
Facilities were nice & clean. Office staff were very friendly & helpful! Rooms were large and very nice & clean! Beautiful views of the Ottauquechee River. Fun grassy area with fire pits & cornhole along the edge of the river. Walking distance to the downtown area with shops & restaurants!

Reviewed on Jun 30, 2026

The Vesper

The Vesper

3 out of 5
Price was CA $2,023, price is now CA $1,690 per person
CA $1,690
per person
Sep 9 - Sep 14
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
9.2/10 Wonderful! (63 reviews)
Absolute gem on the edge of.downtown. super walkable everywhere in terms of shopping, and within a 5 min drive to less pricier food options away from downtown. Jessica was an amazing and gracious host. The oatmeal with maple syrup, apples and walnuts was the quintessential Vermont start to the day. So many unique touches in terms of aesthetics made it feel homey yet held to the character of a nearly 200 year old home. Stay here.

Reviewed on Jun 25, 2026

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was CA $1,902, price is now CA $1,591 per person
CA $1,591
per person
Sep 9 - Sep 14
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty

Reviewed on Dec 1, 2025

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was CA $1,558, price is now CA $1,335 per person
CA $1,335
per person
Sep 18 - Sep 21
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
10/10 Exceptional! (199 reviews)
This was a hidden gem. It was so clean and quiet. Definitely a place for peace and quiet. Rooms were super clean and the attention to detail was amazing. Will definitely be back.

Reviewed on Jun 22, 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 Solstice Ski Lift and Sunrise Express Ski Lift.

Find hotels in Pikes Falls

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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 $217 per night from Jul 7 to Jul 8
CA $217
CA $260 total
Jul 7 - Jul 8
includes taxes & fees
8.6/10 Excellent! (284 reviews)
"Lovely resort although the pool is closed until October. Beautiful, peaceful property. 300+ rooms! Music on patio with s’mores was fun. Karen was very nice and helpful. Only negative it is 15 miles from town and not a lot to do!"

Reviewed on Jun 29, 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
The price is CA $331 per night from Jul 7 to Jul 8
CA $331
CA $423 total
Jul 7 - Jul 8
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 $144 per night from Jul 5 to Jul 6
CA $144
CA $158 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (915 reviews)
"Nice older hotel. Comfortable stay."

Reviewed on Jun 30, 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.
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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 $1,264 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.