Jamaica Vacations from $595
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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.
Mountaineer Inn
Price was $727, price is now $595 per person
$595
per person
Dec 4 - Dec 7
found 2 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (VSF)
8.8/10 Excellent! (507 reviews)
Clean room and spacious. Walkable areas around to explore. Would stay again.
Reviewed on Oct 6, 2025
Deerfield Valley Inn
Price was $2,262, price is now $1,939 per person
$1,939
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
9.6/10 Exceptional! (64 reviews)
We loved our stay in Deerfield Valley Inn. One of the best inns in Southern Vermont that we stayed in. The room was spacious, cozy, clean and elegantly decorated with a fireplace. The staff were super friendly and accommodating. The inn was right in the middle of the town so everything was walking distance. Definitely going back and highly recommend for a relaxing getaway.
Reviewed on Sep 25, 2025
Sinclair Inn Bed and Breakfast
Price was $720, price is now $644 per person
$644
per person
Dec 11 - Dec 14
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
9.8/10 Exceptional! (90 reviews)
Our stay at the Sinclair Inn Bed and Breakfast was nothing short of amazing. The accommodations were beautifully decorated, blending comfort with charm. The common sitting areas were especially inviting, offering the perfect setting to unwind, play a game, or just visit. Each breakfast was different— thoughtfully prepared, and absolutely delicious. The hosts were gracious and attentive, providing warm hospitality that made us feel both welcome and cared for. The grounds were well-kept, enhancing the sense of peace and quiet that made our stay so relaxing. A truly memorable retreat — we look forward to returning.
Reviewed on Oct 4, 2025
The Covered Bridge Inn
Price was $715, price is now $607 per person
$607
per person
Dec 4 - Dec 7
found 2 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (VSF)
7.8/10 Good! (1,003 reviews)
This place is in need of a serious update. The room was relatively clean and the bed pretty comfortable. The property just looks worn down and neglected.
Reviewed on Oct 8, 2025
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.
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.
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.
Jamaica Hotel Deals
The Equinox Golf Resort & Spa
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
$172 nightly
The price is $189 total per night from Nov 2 to Nov 3
$189 total
Nov 2 - Nov 3
Total with taxes and fees
7.2/10 Good! (543 reviews)
"It’s a lovely 200 year old hotel that’s been updated nicely. It’s got 3 restaurants and a wonderful coffee bar in the lobby. The staff is very helpful and courteous."
Reviewed on Oct 3, 2025
Hampton Inn and Suites Manchester
4519 Main St, Manchester Center, VT
$130 nightly
The price is $143 total per night from Nov 2 to Nov 3
$143 total
Nov 2 - Nov 3
Total with taxes and fees
9.6/10 Exceptional! (1,005 reviews)
"Very courteous staff"
Reviewed on Oct 6, 2025
The Covered Bridge Inn
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $114 total per night from Oct 13 to Oct 14
$114 total
Oct 13 - Oct 14
Total with taxes and fees
7.6/10 Good! (1,005 reviews)
"We were initially put off by the look of the outside of this “Inn”! But it turns out we were greeted by a smiling and polite person during check in. The room was large, clean, and comfortable. The bathroom had thick towels and well stocked. All and all it was a very pleasant stay at a very reasonable ..."
Reviewed on Oct 4, 2025
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.
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
