Jamaica Vacations from $706

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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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $901, price is now $706 per person
$706
per person
Feb 19 - Feb 23
found 19 hours ago
Roundtrip flight included
Miami (MIA) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
The staff was super nice and flexible! Location was great

Reviewed on Dec 13, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Save 100% on your flight
Price was $2,153, price is now $1,639 per person
$1,639
per person
Feb 19 - Feb 23
found 19 hours ago
Roundtrip flight included
Miami (MIA) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Very clean, everyone was so nice. Food at restaurant is a little pricey but was very good.

Reviewed on Nov 30, 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Save 100% on your flight
Price was $1,496, price is now $1,185 per person
$1,185
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
9.2/10 Wonderful! (549 reviews)
I stay at Woodstock Inn every December and it never disappoints. The rooms are comfortable and well-appointed, but it's hard to decide whether to enjoy the comforts of the room or sitting in front if the fire in the lobby. I look forward to the next visit.

Reviewed on Dec 13, 2025

Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
Clock Tower Base Area
Save 100% on your flight
Price was $1,984, price is now $1,572 per person
$1,572
per person
Feb 19 - Feb 23
found 19 hours ago
Roundtrip flight included
Miami (MIA) to Springfield (VSF)
8/10 Very Good! (219 reviews)
We really enjoyed our stay at the Mountain Lodge at Okemo, it was clean and our room was newly renovated and very cute. Would definitely recommend!!

Reviewed on Oct 6, 2025

Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
Price was $1,838, price is now $1,542 per person
$1,542
per person
Feb 11 - Feb 14
found 6 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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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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 Stratton Mountain Resort.

Find hotels in Mountain Acres

Discover the most popular places to visit in Jamaica

Jamaica State Park

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

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.

Ball Mountain Dam

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

Jamaica Hotel Deals

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$158 nightly
The price is $172 total per night from Jan 7 to Jan 8
$172 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
8.6/10 Excellent! (927 reviews)
Yea

Reviewed on Dec 12, 2025

Pointe at Castle Hill Resort
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way West Dover VT
$336 nightly
The price is $369 total per night from Dec 22 to Dec 23
$369 total
Dec 22 - Dec 23
Total with taxes and fees
8.6/10 Excellent! (243 reviews)
Amazing 2 big hot tubes and warm swim pool on the open air !!! A lot of restaurants around and Beautiful nature! But chairlifts was closed- so check availability

Reviewed on Oct 18, 2025

Mount Snow Grand Summit 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
$223 nightly
The price is $245 total per night from Jan 12 to Jan 13
$245 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
7.4/10 Good! (576 reviews)
Nicely decorated for Christmas. Helpful and attentive staff, Lack of heat in some of the public areas like near the library was an issue, but they tried by keeping the fireplace going. As a helpful hint- the fireplace area in the library was drafty and cold. You can go a long way toward fixing this ...

Reviewed on Dec 7, 2025

The Equinox Golf Resort & Spa
See all 2,573 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 $706 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.