Jamaica Vacations from $509

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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.

The Latest Jamaica vacation packages

Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $561, price is now $509 per person
$509
per person
May 29 - May 31
just found
Roundtrip flight included
Minneapolis (MSP) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Clean, staff was great.

Reviewed on Dec 23, 2025

Treehouse Home in Ludlow

Treehouse Home in Ludlow

2 out of 5
Price was $1,771, price is now $1,509 per person
$1,509
per person
May 29 - May 31
just found
Roundtrip flight included
Minneapolis (MSP) to Springfield (VSF)
No reviews
The Hartness House

The Hartness House

3 out of 5
Price was $675, price is now $612 per person
$612
per person
May 29 - May 31
just found
Roundtrip flight included
Minneapolis (MSP) to Springfield (VSF)
8.2/10 Very Good! (328 reviews)
So be aware, YOU ARE PROBABLY NOT SLEEPING IN THE BEAUTIFUL MANSION. There is long ugly gray motel in the back, where the rooms actually are. Our host was lovely on check in & I kinda feel bad for this tepid review but as our friend said "this place has all the charm of a upscale Motel 6". Our room was clean & ok for a nights sleep though & the price was right for us. Room 24's bed had the DREADED "constantly roll into the middle of the mattress" SWALE in it, our friends said, so maybe they could replace that. The motel connects to the mansion & your are kindly told you can come, "check it out at night & in the morning there is continental breakfast & coffee" here. I actually wish they opened the beautiful bar on the weekend so we could have sat there & had a drink instead of going back to the Motel 6. Anyway, it was fine, but not exactly what we expected.

Reviewed on Feb 10, 2026

Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
Price was $591, price is now $543 per person
$543
per person
May 29 - May 31
just found
Roundtrip flight included
Minneapolis (MSP) to Springfield (VSF)
8.8/10 Excellent! (25 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty

Reviewed on Dec 1, 2025

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Where to stay in Jamaica

Find the best Jamaica areas and neighborhoods for the activities you enjoy most. Learn more about Jamaica
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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

Discover the most popular places to visit in Jamaica

Jamaica State Park

4.5/5(4 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.

Jamaica State Park

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.

Margie's Muse Handweaving & Gallery

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.

Hot Glass Works

Jamaica Hotel Deals

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$146 nightly
The price is $159 total per night from Mar 9 to Mar 10
$159 total
Mar 9 - Mar 10
Total with taxes and fees
8.8/10 Excellent! (998 reviews)
Excellent for a family stay

Reviewed on Mar 1, 2026

Pointe at Castle Hill Resort
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
$168 nightly
The price is $185 total per night from Apr 1 to Apr 2
$185 total
Apr 1 - Apr 2
Total with taxes and fees
7.4/10 Good! (598 reviews)
Beautiful hotel. Nice pool and gym.

Reviewed on Feb 19, 2026

The Equinox Golf Resort & Spa
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

3 out of 5
5383 Main St Manchester Center VT
Fully refundable
$104 nightly
The price is $115 total per night from Mar 24 to Mar 25
$115 total
Mar 24 - Mar 25
Total with taxes and fees
8.4/10 Very Good! (906 reviews)
The room was not clean and smelled strongly of cigarettes

Reviewed on Feb 28, 2026

The Palmer House Resort, an Ascend Collection Hotel
See all 2,646 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

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Frequently asked questions

How much does a Jamaica vacation package cost?
You'll find cheap prices from $509 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.