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Jamaica

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Jamaica Flights as Low as $133

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Wed, Jun 3 - Wed, Jun 10
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$133 Roundtrip, found 1 day ago
$133
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Jun 3 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Jun 10, priced at $133 found 1 day ago
JetBlue Airways
Thu, May 28 - Wed, Jun 10
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, May 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Jun 10, priced at $171 found 1 day ago
JetBlue Airways
Mon, Jun 1 - Wed, Jun 10
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Jun 1 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Jun 10, priced at $177 found 1 day ago
Cape Air
Tue, Apr 21 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$178 Roundtrip, found 3 hours ago
$178
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Tue, Apr 21 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $178 found 3 hours ago
Cape Air
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 3 hours ago
$180
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $180 found 3 hours ago
JetBlue Airways
Tue, Apr 21 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$183 Roundtrip, found 3 hours ago
$183
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Tue, Apr 21 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $183 found 3 hours ago
Cape Air
Tue, Apr 21 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$184 Roundtrip, found 3 hours ago
$184
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Tue, Apr 21 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $184 found 3 hours ago
Cape Air
Sat, May 30 - Fri, Jun 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$186 Roundtrip, found 3 hours ago
$186
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Jun 12, priced at $186 found 3 hours ago
JetBlue Airways
Tue, Apr 21 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$188 Roundtrip, found 3 hours ago
$188
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Tue, Apr 21 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $188 found 3 hours ago
Cape Air
Sun, May 31 - Fri, Jun 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$189 Roundtrip, found 3 hours ago
$189
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Sun, May 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Jun 12, priced at $189 found 3 hours ago
Cape Air
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$190 Roundtrip, found 3 hours ago
$190
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $190 found 3 hours ago
JetBlue Airways
Sun, May 31 - Fri, Jun 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$194 Roundtrip, found 3 hours ago
$194
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Sun, May 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Jun 12, priced at $194 found 3 hours ago
Cape Air
Sun, May 31 - Sat, Jun 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$194 Roundtrip, found 1 day ago
$194
Roundtrip
found 1 day ago
Select Cape Air flight, departing Sun, May 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Jun 13, priced at $194 found 1 day ago
JetBlue Airways
Sat, May 30 - Fri, Jun 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$196 Roundtrip, found 3 hours ago
$196
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Jun 12, priced at $196 found 3 hours ago
Cape Air
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$196 Roundtrip, found 3 hours ago
$196
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $196 found 3 hours ago
Delta
Fri, Apr 3 - Sun, Apr 5
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$810 Roundtrip, found 3 days ago
$810
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Apr 3 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sun, Apr 5, priced at $810 found 3 days ago

Cheap Flights to Jamaica

Fall in love at first flight with your vacation to Jamaica by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Jamaica on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Jamaica, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Jamaica

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Jamaica with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the VSF airport.

What is the cheapest month to fly to Jamaica?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Jamaica are in June, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Jamaica?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Jamaica.

What airport is best to fly into Jamaica?

When you’re planning your trip to Jamaica, convenience is the name of the game. Luckily, Jamaica Hartness State Airport is nearby so you can deplane and get going on checking off everything on your Jamaica must-do list.

How much are flights to Jamaica?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Jamaica on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $133, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Jamaica?

The trick to saving a stack of cash on your flight to Jamaica? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $133 right now, why wait?

Jamaica Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$133

Last Minute Hotel Deals in Jamaica

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (1,001 reviews)
Have stayed here many times. Close to town and Okemo. Very convenient.

Reviewed on Mar 30, 2026

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Pointe at Castle Hill Resort
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

2 out of 5
270 Handle Rd West Dover VT
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and Heavy Metal Ski Lift are ...
8.6/10 Excellent! (80 reviews)
The bath soap container was empty. I asked a hotel staff member if she could refill the dispenser and she said she would bring it to my room in a few minutes. She never showed up as promised. I passed her on the way out 45 minutes later. She look at me and went on her business.

Reviewed on Mar 22, 2026

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Hideaway Inn Mt. Snow
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St Manchester Center VT
Book a stay at this business-friendly hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
9.6/10 Exceptional! (1,002 reviews)
Great business center and laundry facilities.

Reviewed on Apr 1, 2026

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Hampton Inn and Suites Manchester
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
Book a stay at this golf hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (926 reviews)
it's all good

Reviewed on Apr 2, 2026

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

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A Manchester VT
Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American ...
7.4/10 Good! (607 reviews)
We love the Equinox. We usually stay here during ski season. Always looking forward to rest after a long day of ski. Amenities are amazing, the restaurant and bar are great to eat and hangout.

Reviewed on Mar 30, 2026

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The Equinox Golf Resort & Spa
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
Book a stay at this spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,000 reviews)
Plenty of parking Clean - no bugs Goes downhill from there. Front desk people were polite but far from friendly. Major renovations need to be done before I will come back. Windows did not lock, which my husband discovered as we were getting ready for bed. He decided that they were too small for anyone ...

Reviewed on Mar 30, 2026

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Colonial Motel And Spa
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Book a stay at this golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
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Kimpton Taconic Hotel by IHG
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and 2 hot tubs. Popular attractions Mount Snow and Tumbleweed Ski Lift are ...
8.6/10 Excellent! (266 reviews)
Room was on the small side and it's usually standard that the room have a pull our sofa bed but ours did not. Rooms had a small full kitchen which is really great. The location was amazing, right on the mountain and everything you need to ski is right there. It's also nice to be able to stroll to ...

Reviewed on Mar 19, 2026

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Grand Summit Resort, A Vail Resorts Property
See all 2,644 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.