Jamaica Vacations from $542

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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.

The Latest Jamaica vacation packages

Price found within the past 48 hours. Click for updated prices.
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was $631, price is now $542 per person
$542
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Springfield (VSF)
9.4/10 Exceptional! (128 reviews)
Good price, really quite, clean, person on site very friendly helpful with places we can go & things to do I recommend the place

Reviewed on Jul 25, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $2,708, price is now $2,075 per person
$2,075
per person
Oct 15 - Oct 20
just found
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8.8/10 Excellent! (968 reviews)

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $1,602, price is now $1,320 per person
$1,320
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
9.2/10 Wonderful! (121 reviews)

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $949, price is now $801 per person
$801
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8.6/10 Excellent! (297 reviews)
Host in restaurant let us stand at the host stand while he finished up his conversation with friends or regulars at bar until he realized to seat us. Took over 45 minutes to get a hamburger and pork slider sliders. Served to us at 9:00 pm sat at 8:10pm. Needed to hurry because they played the “Closing Time “ song 3 times in a row as they served us. Oh and we were the only couple in the dinning area. So no other orders were in the kitchen since we arrived. Felt pushed out after or order took over 45 minutes to arrive.

Reviewed on Aug 3, 2026

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $679, price is now $574 per person
$574
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Springfield (VSF)
8.6/10 Excellent! (876 reviews)
Beautiful resort. I love it!

Reviewed on Aug 4, 2026

Don't see what you're looking for?
See all available trips from Columbus to Jamaica
View all trips

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 Stratton Mountain Resort.

Find hotels in Pikes Falls

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

Jamaica Hotel Deals

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
$280 nightly
The price is $308 total per night from Sep 2 to Sep 3
$308 total
Sep 2 - Sep 3
Total with taxes and fees
9.4/10 Exceptional! (860 reviews)
"Excellent amenities and perfect if you're traveling with a dog to VT. Rooms are very nice albeit a bit small and very low water pressure in the shower."

Reviewed on Aug 3, 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
$118 nightly
The price is $130 total per night from Aug 10 to Aug 11
$130 total
Aug 10 - Aug 11
Total with taxes and fees
8.6/10 Excellent! (945 reviews)
"Main Street Brattleboro so great, near Restaurants and entertainment. We saw a film downstairs, LPs and are Record player in Rooms!"

Reviewed on Aug 3, 2026

Latchis Hotel
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A Manchester VT
Fully refundableReserve now, pay when you stay
$201 nightly
The price is $221 total per night from Aug 24 to Aug 25
$221 total
Aug 24 - Aug 25
Total with taxes and fees
7.4/10 Good! (657 reviews)
"Good place to stay, but not great."

Reviewed on Aug 4, 2026

The Equinox Golf Resort & Spa
See all 2,583 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.

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

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Jamaica vacation package cost?
You'll find cheap prices from $542 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.