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.
Colonial Motel
CA $1,064
per person
Nov 30 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
6.6/10 (61 reviews)
It was filthy. huge stains on rug. everything was dirty the bathroom dirty writing on the bathroom moulding "Mel +Tyler "24". The lamp shades were dirty.I opened the Fridge to put my insulin In it..It was full of black Bugs and mould. We came in at 10.00 pm exhausted. my husband is older and sick.so we slept in the bed ..that was clean. It was terrible. We told the office in Am they said we should of told them. I have pictures and showed them .
Reviewed on Sep 28, 2026
Latchis Hotel
CA $1,238
per person
Nov 30 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (989 reviews)
This place is a gem.
I love and like the proximity to the train station, Brattleboro Food Coop, River Art School and Brattleboro Museum and Art Center,
I visited twice: first with my teen son and husband, and the second by myself, and both times were great.
There are signs of the passing of time in this lovely Art Deco structure, and that adds to its beauty,
Super courteous staff
The first time we watched a movie, so if you stay at the hotel, please treat yourself to that or some of their baskets.
I missed eating at their restaurant, so I guess next time.
My husband loved that there was always coffee for him, and my son loved our mini fridge and microwave.
We love the history of this place and how is part of the larger arts and culture scene of Brattleboro
Reviewed on Sep 28, 2026
Sinclair Inn Bed and Breakfast
CA $1,252
per person
Nov 30 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
10/10 Exceptional! (124 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 $1,491
per person
Nov 30 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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 Sunrise Express 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
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
CA $212
CA $254 total
Oct 28 - Oct 29
includes taxes & fees
8.6/10 Excellent! (312 reviews)
"What I like is the room was well stocked, very clean and the staff is very helpful. What I did not like is the parking is very inconvenient and is quite a walk which is never fun in bad weather. They need more luggage carts. It looked like they have about 5 or 6 for about a 200 room hotel. There ..."
Reviewed on Sep 27, 2026
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
CA $125
CA $138 total
Sep 30 - Oct 1
includes taxes & fees
6.6/10 (69 reviews)
"It was filthy. huge stains on rug. everything was dirty the bathroom dirty writing on the bathroom moulding "Mel +Tyler "24". The lamp shades were dirty.I opened the Fridge to put my insulin In it..It was full of black Bugs and mould. We came in at 10.00 pm exhausted. my husband is older and sick.so ..."
Reviewed on Sep 28, 2026
The Manchester View
77 High Meadow Way & VT-7A Manchester Center VT
Fully refundableReserve now, pay when you stay
CA $152
CA $167 total
Oct 26 - Oct 27
includes taxes & fees
9.4/10 Exceptional! (909 reviews)
"We really enjoyed our stay at The Manchester View. Our terrace room was spacious and comfortable, and the view was absolutely to die for—definitely one of the highlights of our stay. Check-in and checkout were both very easy, and the included breakfast was a nice touch and a great way to start the ..."
Reviewed on Sep 28, 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 $1,064 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.
