Jamaica Vacations from $675

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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.
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
Price was $912, price is now $675 per person
$675
per person
Jun 6 - Jun 13
found 11 hours ago
Roundtrip flight included
Nashville (BNA) to Springfield (VSF)
8.2/10 Very Good! (967 reviews)
Had a great stay, staff friendly. Breakfast, lots of options - simple but great for our family. Everything we needed, we will be back.

Reviewed on May 5, 2026

Latchis Hotel

Latchis Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,102, price is now $754 per person
$754
per person
Jun 6 - Jun 13
found 11 hours ago
Roundtrip flight included
Nashville (BNA) to Springfield (VSF)
8.6/10 Excellent! (871 reviews)
Very well run hotel, conveniently located in the heart of Brattleboro. Free parking in a lot next to the hotel was a nice touch. My only gripe would be that my room (104) had no view as the windows were made of some kind of stained glass that you can't see through and couldn't open. Also they could not be closed all the way and allowed a cold draft to come through on a chilly night. I had to stuff towels in the open gaps to keep the chill out. A little strange I thought, but was manageable.

Reviewed on May 4, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Save 100% on your flight
Price was $1,850, price is now $1,294 per person
$1,294
per person
Jun 6 - Jun 13
found 11 hours ago
Roundtrip flight included
Nashville (BNA) to Springfield (VSF)
8.8/10 Excellent! (922 reviews)
The Shire is in a wonderful location and I would recommend for a short stay. They are in the midst of a renovation and the rooms and exterior are nice and well kept. My only issue was that the coffee bars were not well stocked all the time with the same variety and the ice machine was not well stocked as it ran out of water to produce ice during our 2 night stay. Otherwise, the place and location is wonderful.

Reviewed on Apr 19, 2026

Chalet 239

Chalet 239

2 out of 5
Save 100% on your flight
Price was $1,027, price is now $721 per person
$721
per person
Jun 6 - Jun 13
found 11 hours ago
Roundtrip flight included
Nashville (BNA) to Springfield (VSF)
9.4/10 Exceptional! (124 reviews)
Only issue is there was nowhere to hang anything and the room was very small. Room was clean, comfortable and bathroom was well-appointed. Breakfast was good and staff friendly and helpful. Close to restaurants and super easy access to Mt. Snow. Would definitely stay here again.

Reviewed on Mar 28, 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 $1,031, price is now $764 per person
$764
per person
Jun 6 - Jun 13
found 11 hours ago
Roundtrip flight included
Nashville (BNA) to Springfield (VSF)
8.6/10 Excellent! (852 reviews)
No inflatable mattress offered anymore.

Reviewed on Mar 18, 2026

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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 Stratton Mountain Resort and American Express Ski Lift.

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

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

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

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
$201 nightly
The price is $221 total per night from May 25 to May 26
$221 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (840 reviews)
We always love this property!!

Reviewed on May 4, 2026

Kimpton Taconic Hotel by IHG
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
$154 nightly
The price is $170 total per night from May 17 to May 18
$170 total
May 17 - May 18
Total with taxes and fees
7.4/10 Good! (618 reviews)
We have been coming here for almost twenty years. The property could use a little tlc, but it also has a lot of charm. Pablo at the front desk was the best attendant we have ever had. He really made the experience better. Our AC was not working but within minutes an engineer came up and was able ...

Reviewed on Apr 30, 2026

The Equinox Golf Resort & Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $134 total per night from Jun 7 to Jun 8
$134 total
Jun 7 - Jun 8
Total with taxes and fees
8.2/10 Very Good! (970 reviews)
Had a great stay, staff friendly. Breakfast, lots of options - simple but great for our family. Everything we needed, we will be back.

Reviewed on May 5, 2026

Hampton Inn Brattleboro
See all 2,625 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 $675 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.