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.
Latchis Hotel

Latchis Hotel

CA $971
per person
Dec 11 - Dec 14
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (992 reviews)
Had a wonderful stay. Great room with a beautiful view of the mountains. And we absolutely loved that every room had a record player with historic records to play and enjoy - what a cool feature!

Reviewed on Oct 18, 2026

Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

CA $1,104
per person
Dec 6 - Dec 8
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
10/10 Exceptional! (127 reviews)
We had a wonderful stay at the Sinclair Inn Bed & Breakfast in Jericho, Vermont! The house is absolutely beautiful—a charming Queen Anne Victorian filled with character and historic charm. We stayed in Room 5 upstairs, which featured a comfortable king bed and a private bathroom. It was a lovely, comfortable place to relax and enjoy our visit. Kyle, Holly, and their daughter Cassidy were amazing hosts! They went above and beyond to make us feel welcome. Earlier in our trip, before arriving at the Sinclair Inn, I had injured myself and was on crutches. When we arrived, Kyle graciously helped my wife carry our suitcases upstairs to our room. That thoughtful gesture meant so much to us and really showed the kindness and genuine hospitality of this wonderful family. Breakfast was delicious, and one of the things we especially enjoyed was the opportunity to sit down, meet, and talk with the other guests. Those conversations added a personal touch to our stay and made the experience even more enjoyable. Between the beautiful Victorian home, the comfortable accommodations, the delicious breakfast, and the outstanding hospitality, our stay was truly memorable. We highly recommend the Sinclair Inn to anyone visiting Vermont. If you're looking for a beautiful bed and breakfast with wonderful hosts who genuinely care about their guests, this is the place! We would absolutely love to stay here again.

Reviewed on Oct 18, 2026

1846 Inn and Tavern

1846 Inn and Tavern

CA $1,240
per person
Dec 11 - Dec 14
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
10/10 Exceptional! (1 review)
The Inn also has an adjacent nice food tavern and music this weekend. Friendly host - embodied the helpful spirit of old inns. Helped with allowing a late dinner due to late arrival. Adjusted the heat for us and allowed us to set a bit extra in their library. Very welcoming. A ++ for hospitality and making us welcome!

Reviewed on Oct 12, 2026

Hampton Inn Brattleboro

Hampton Inn Brattleboro

CA $1,019
per person
Dec 11 - Dec 14
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.2/10 Very good! (1,003 reviews)
Excellent place to stay, clean seems new, has small pool and water bath (kind of like jacuzzi) clean room, staff is nice and friendly. Includes breakfast and all day coffee or hot water to make teas (that is a must for me) as I need to make me teas few times a day. Would recommend for sure. If it was cheaper than it would really be off the charts but I will not include that into the review.

Reviewed on Oct 19, 2026

Colonel Williams Inn

Colonel Williams Inn

CA $1,069
per person
Dec 11 - Dec 14
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
9.8/10 Exceptional! (359 reviews)
Very unique B&B. Please note all rooms are upstairs, a steep, narrow case. We did not take in suitcases. Our room #8 had bathroom across a hall although we were told it was only ours. So a few unexpected twists. Bed was comfortable. Only one chair in room. Breakfast was tasty with numerous items available. Remote location with beautiful fall colors surrounding.

Reviewed on Oct 9, 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 Sunrise Express Ski Lift and Villager Ski Lift.

Default Image

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.

Default Image

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?

Choose your dates

Jamaica Hotel Deals

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

89 Grand Summit Way West Dover VT
Fully refundable
CA $211
CA $252 total
Nov 17 - Nov 18
includes taxes & fees
8.6/10 Excellent! (323 reviews)
"Hot tub wasn’t up and running, was looking forward to utilizing that amenity. Food was basically just freezer food, even the salads were below average. Service was great though."

Reviewed on Oct 17, 2026

Grand Summit Resort, A Vail Resorts Property
Aspen At Manchester

Aspen At Manchester

5669 Main Street Manchester Center VT
Fully refundableReserve now, pay when you stay
CA $158
CA $189 total
Nov 2 - Nov 3
includes taxes & fees
8.8/10 Excellent! (707 reviews)
"It was very modern looking well renovated properties a hole, and we were very well taken care of throughout our one night there."

Reviewed on Oct 17, 2026

Aspen At Manchester
The Manchester View

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT
Fully refundableReserve now, pay when you stay
CA $143
CA $158 total
Nov 3 - Nov 4
includes taxes & fees
The Manchester View
See all 2,625 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.

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

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.
See properties

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.
See properties

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.
See properties

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.
See properties

Frequently asked questions

How much does a Jamaica vacation package cost?
You'll find cheap prices from CA $971 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.