Jamaica Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 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
Top Flight + Hotel Deals in Jamaica
Price found within the past 48 hours. Click for updated prices.
Mountain Lodge at Okemo, A Vail Resorts Property
Clock Tower Base Area
€577
per person
10 Oct - 12 Oct
found 14 hours ago
Return direct flight included
New York (NYC) to Springfield (VSF)
8/10 Very good! (225 reviews)
Staff was very helpful, the property is very clean, the room was clean with lots of space. The kitchen had a full size refrigerator and microwave. I was very happy overall
Reviewed on 19 Jul 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
€736
per person
10 Oct - 12 Oct
found 14 hours ago
Return direct flight included
New York (NYC) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.
Reviewed on 26 Jun 2025
1br Ski-in, Ski-out With King Bed- Okemo Mtn Lodge 1 Bedroom Condo by RedAwning
Clock Tower Base Area
€743
per person
10 Oct - 12 Oct
found 14 hours ago
Return direct flight included
New York (NYC) to Springfield (VSF)
6.8/10 (3 reviews)
I was promised the fire place worked. that is the only reason I booked the place. I expect a portion 0f what I
spent returned.
Reviewed on 26 Sept 2022
Where to stay in Jamaica
Find the best Jamaica areas and neighborhoods for the activities you enjoy most. Learn more about Jamaica
Pikes Falls
While there might not be top attractions in Pikes Falls, you can explore the larger area and discover places like Solstice Ski Lift and Sunrise Express Ski Lift.
Mountain Acres
Though Mountain Acres may not have many top sights, you can venture to the surrounding area to see attractions like Jamaica State Park and Tamarack Ski Lift.
East Jamaica
If you're spending some time in East Jamaica, Green Mountain National Forest and West River are top sights worth seeing.
Top hotels in Jamaica
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
€242
9 Sept - 10 Sept
includes taxes & fees
9.4/10 Exceptional! (862 reviews)
"A few unexpected extra charges for property fees"
Reviewed on 17 Aug 2026
The Equinox Golf Resort & Spa
3567 Main Street Route 7A Manchester VT
Fully refundableReserve now, pay when you stay
€200
8 Sept - 9 Sept
includes taxes & fees
7.4/10 Good! (660 reviews)
"The bed sunk into the middle and had no support and the shower didn’t drain so you had to shower in standing water Overall rooms were tired and needed updating Poor lighting in bathroom vanity area."
Reviewed on 23 Aug 2026
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
€77
20 Sept - 21 Sept
includes taxes & fees
6.8/10 (46 reviews)
"It was dirty. The sink, bathroom, tub, floors. All dead bugs all over. TV was great. But a very musty smell in room. My sheets were not dry when we went to bed."
Reviewed on 26 Aug 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.
Hot Glass Works
You can spend an afternoon studying the exhibits at Hot Glass Works 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 such as skiing in Jamaica. Discover the mountain views in this quaint area.
Margie's Muse Handweaving & Gallery
You can spend an afternoon studying the exhibits at Margie's Muse Handweaving & Gallery in Jamaica. Discover the mountain views in this quaint area or enjoy its ski slopes.
Frequently asked questions
How much does a Jamaica holiday package cost?
You'll find cheap prices from €577 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 holiday to Jamaica costs.
What are the cheapest months to go to Jamaica?
To pick up cheap Jamaica holiday packages, plan your getaway outside of peak periods like public holidays and major festivals. You'll typically find lower prices and better availability in the off-season or when it's less busy.
How many days is enough for Jamaica?
With around 3 days, you'll have plenty of time to visit popular neighbourhoods like Rawsonville and Forest Farms during your Jamaica holiday. Remember to also add Hot Glass Works and Ball Mountain Dam to your must-do list. Looking for more adventures? Consider exploring outside of Jamaica on tours and day trips.
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 customise 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Jamaica holiday as a package?
Expedia holiday 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 customised Jamaica holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday 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.
How to plan a trip to Jamaica?
- Choose when to travel: Check your schedule and get packing. Your favourite time of year and the activities on offer will also help you decide when to visit Jamaica.
- Set a budget: Factor in costs like flights, meals and transportation when calculating how much to set aside for your trip to Jamaica. Then, choose a property that matches your budget, whether that's a low-cost stay or a high-end retreat.
- Set the duration of your trip: Start by making a list of all the activities and sights you'd like to get to in Jamaica. Then, estimate how long you'll need for each, as well as any travel time.
- Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick a Jamaica holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
