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Jamaica

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Jamaica Flights as Low as $131

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

JetBlue Airways
Fri, May 15 - Wed, May 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$131 Roundtrip, found 13 hours ago
$131
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Fri, May 15 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, May 27, priced at $131 found 13 hours ago
JetBlue Airways
Tue, Apr 7 - Sat, Apr 18
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$136 Roundtrip, found 14 hours ago
$136
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Tue, Apr 7 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Apr 18, priced at $136 found 14 hours ago
JetBlue Airways
Tue, May 12 - Wed, May 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$163 Roundtrip, found 13 hours ago
$163
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Tue, May 12 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, May 27, priced at $163 found 13 hours ago
JetBlue Airways
Mon, May 11 - Wed, May 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$165 Roundtrip, found 13 hours ago
$165
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Mon, May 11 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, May 27, priced at $165 found 13 hours ago
JetBlue Airways
Sun, May 10 - Wed, May 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$167 Roundtrip, found 13 hours ago
$167
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Sun, May 10 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, May 27, priced at $167 found 13 hours ago
JetBlue Airways
Tue, Apr 28 - Sat, May 9
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$169 Roundtrip, found 14 hours ago
$169
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Tue, Apr 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 9, priced at $169 found 14 hours ago
JetBlue Airways
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$174 Roundtrip, found 14 hours ago
$174
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $174 found 14 hours ago
JetBlue Airways
Wed, Apr 22 - Mon, May 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$178 Roundtrip, found 14 hours ago
$178
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Wed, Apr 22 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, May 11, priced at $178 found 14 hours ago
Cape Air
Thu, May 14 - Mon, Jun 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 13 hours ago
$180
Roundtrip
found 13 hours ago
Select Cape Air flight, departing Thu, May 14 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 1, priced at $180 found 13 hours ago
Cape Air
Thu, May 28 - Mon, Jun 15
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$182 Roundtrip, found 13 hours ago
$182
Roundtrip
found 13 hours ago
Select Cape Air flight, departing Thu, May 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 15, priced at $182 found 13 hours ago
Cape Air
Wed, Apr 22 - Sat, May 9
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$185 Roundtrip, found 13 hours ago
$185
Roundtrip
found 13 hours ago
Select Cape Air flight, departing Wed, Apr 22 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 9, priced at $185 found 13 hours ago
Cape Air
Thu, May 14 - Mon, Jun 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$186 Roundtrip, found 13 hours ago
$186
Roundtrip
found 13 hours ago
Select Cape Air flight, departing Thu, May 14 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 1, priced at $186 found 13 hours ago
Cape Air
Tue, Apr 28 - Mon, May 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$187 Roundtrip, found 14 hours ago
$187
Roundtrip
found 14 hours ago
Select Cape Air flight, departing Tue, Apr 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, May 11, priced at $187 found 14 hours ago
Cape Air
Thu, May 28 - Mon, Jun 15
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$187 Roundtrip, found 13 hours ago
$187
Roundtrip
found 13 hours ago
Select Cape Air flight, departing Thu, May 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 15, priced at $187 found 13 hours ago
JetBlue Airways
Wed, Apr 22 - Wed, Apr 29
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$189 Roundtrip, found 14 hours ago
$189
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Wed, Apr 22 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Apr 29, priced at $189 found 14 hours ago
JetBlue Airways
Thu, Mar 26 - Sun, Apr 5
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$461 Roundtrip, found 2 days ago
$461
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sun, Apr 5, priced at $461 found 2 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 May, 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 $131, 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 $131 right now, why wait?

Jamaica Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$131

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! (1,002 reviews)
Yes

Reviewed on Mar 11, 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 ...
8.8/10 Excellent! (70 reviews)
Great location. Clunky check-in as all virtual. Hot tub, which is the reason booked was broken, saunas did not heat up, could not adjust the heat in the room, so even though we tried to turn it off it was 80’ overnight. Machine for tea also didn’t work. Clean rooms but the hot tub and heat issues ...

Reviewed on Mar 10, 2026

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Hideaway Inn Mt. Snow
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! (912 reviews)
The staff and maintenance services are great and the breakfast was really nice. However, the amenities area (separate building with the pool, hot tub and workout room) are dilapidated and require serious updating. I'm not sure these amenities should even qualify to be listed considering their condition ...

Reviewed on Mar 9, 2026

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The Palmer House Resort, an Ascend Collection Hotel
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! (1,003 reviews)
The breakfast was great for our family. There is a coffee/tea/cocoa station in place all day. The pool area and hot tub were immaculate and fun for all.

Reviewed on Mar 11, 2026

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Hampton Inn and Suites Manchester
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! (603 reviews)
Hot tub nor sauna we’re working. This is pretty important for a ski Hotel, or anyone that bills themselves as a spa.

Reviewed on Mar 11, 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 (1,002 reviews)
It was good to have pool option after a ski day

Reviewed on Mar 10, 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. ...
9.4/10 Exceptional! (834 reviews)
Hotel was lovely. Beautifully appointed. Staff was excellent and very helpful.

Reviewed on Feb 27, 2026

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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! (262 reviews)
Staff were all friendly. Room was clean. Food at the resort restaurant was great. We have been stay at this hotel many times in the past but were delighted seeing there are on site EV charging stations now. It is a nice add-on. However, one may be lucky or unlucky to get a charging space when stay ...

Reviewed on Mar 9, 2026

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Grand Summit Resort, A Vail Resorts Property
See all 2,633 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.