Jamaica Vacations from $508
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
The Latest Jamaica vacation packages
Price found within the past 48 hours. Click for updated prices.
Vikings Villages Resort
$508
per person
Oct 30 - Nov 1
found 6 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
10/10 Exceptional! (232 reviews)
The place was a dream come true. Beautifully and meticulously maintained. Owners are an amazing couple, super thoughtful and helpful. Already planning a second trip!
Reviewed on Sep 20, 2026
Deerfield Valley Inn
$629
per person
Oct 23 - Oct 25
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
9.4/10 Exceptional! (132 reviews)
Beautiful room in quaint inn with very comfortable bed. Oz, the owner, was an absolute gentleman, kind and helpful.
Reviewed on Sep 14, 2026
Sinclair Inn Bed and Breakfast
$640
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
10/10 Exceptional! (123 reviews)
Such a charming place with warm and friendly hosts. Room was comfortable and had everything we needed. Breakfast was delightful and delicious, serving locally sourced ingredients. Will definitely stay again. 10/10 recommend.
Reviewed on Sep 18, 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 Villager Ski Lift.
East Jamaica
While visiting East Jamaica, you might make a stop by sights like Green Mountain National Forest and West River.
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.
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.
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.
Jamaica Hotel Deals
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
$163 nightly
$179 total
Oct 20 - Oct 21
Total with taxes and fees
8.6/10 Excellent! (309 reviews)
"Very clean. Staff were super helpful. Beautiful even though it was “off-season”."
Reviewed on Sep 15, 2026
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$84 nightly
$93 total
Sep 27 - Sep 28
Total with taxes and fees
6.6/10 (59 reviews)
"This place has potential if it was renovated. The room was bigger than I’ve ever seen which was helpful BUT it was old. Mattress , drapes , sheets were ugly old and dirty Details matter, clean everything . The smell in the rooms was gross. , had to sleep with windows open and still didn’t help"
Reviewed on Sep 20, 2026
The Manchester View
77 High Meadow Way & VT-7A Manchester Center VT
Fully refundableReserve now, pay when you stay
$122 nightly
$135 total
Sep 21 - Sep 22
Total with taxes and fees
9.4/10 Exceptional! (901 reviews)
"Beautiful! Can’t wait to visit again."
Reviewed on Sep 19, 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.
Find the Best Jamaica Vacation Packages
Jamaica Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Rutland Southern Vermont Regional Airport (RUT) |
Population | 1,000 |
Max Temp Winter | 25ºF |
Max Temp Summer | 75ºF |
Top Sights | Mount Snow, Bromley Mountain Ski Resort and Magic Mountain Ski Resort |
More vacations you might like
Frequently asked questions
How much does a Jamaica vacation package cost?
You'll find cheap prices from $508 on Expedia for your Jamaica break. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Jamaica costs.
What are the cheapest months to go to Jamaica?
You can typically find lower prices and better availability in April, May and October. Check out our cheap Jamaica vacation packages and you could get some excellent off-season deals.
How many days is enough for Jamaica?
Dedicate around 3 days for your Jamaica vacation if you're hoping to immerse yourself in everything that makes this destination special. Explore key areas, including Forest Farms and Mountain Acres. Then head to the top attractions such as Ball Mountain Dam and Margie's Muse Handweaving & Gallery. With a well-organized itinerary, you can keep busy with room for some me-time too. Want to venture outside of Jamaica? Consider squeezing in an excursion or two.
How to find the best Jamaica package deals?
Landing a cheap Jamaica package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Jamaica package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Jamaica vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component individually. And you'll still have the flexibility to create a customized Jamaica vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Jamaica?
If you're planning an impromptu Jamaica trip, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score incredible deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Jamaica vacation packages?
If you're like us, you love jet-setting around the world but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Jamaica trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
