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Jamaica

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Jamaica Flights as Low as $237

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

Cape Air
Fri, Aug 7 - Fri, Aug 7
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$237 Roundtrip, found 4 days ago
$237
Roundtrip
found 4 days ago
Select Cape Air flight, departing Fri, Aug 7 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Aug 7, priced at $237 found 4 days ago
Delta
Tue, Oct 13 - Tue, Oct 20
BWI
Baltimore Washington Intl. Thurgood Marshall
RUT
Rutland Southern Vermont Regional
$368 Roundtrip, found 18 hours ago
$368
Roundtrip
found 18 hours ago
Select Delta flight, departing Tue, Oct 13 from Baltimore Washington Intl. Thurgood Marshall to Rutland Southern Vermont Regional, returning Tue, Oct 20, priced at $368 found 18 hours ago
Delta
Tue, Oct 13 - Tue, Oct 20
BWI
Baltimore Washington Intl. Thurgood Marshall
RUT
Rutland Southern Vermont Regional
$378 Roundtrip, found 18 hours ago
$378
Roundtrip
found 18 hours ago
Select Delta flight, departing Tue, Oct 13 from Baltimore Washington Intl. Thurgood Marshall to Rutland Southern Vermont Regional, returning Tue, Oct 20, priced at $378 found 18 hours ago
Delta
Tue, Oct 13 - Tue, Oct 20
BWI
Baltimore Washington Intl. Thurgood Marshall
RUT
Rutland Southern Vermont Regional
$388 Roundtrip, found 18 hours ago
$388
Roundtrip
found 18 hours ago
Select Delta flight, departing Tue, Oct 13 from Baltimore Washington Intl. Thurgood Marshall to Rutland Southern Vermont Regional, returning Tue, Oct 20, priced at $388 found 18 hours ago
Delta
Tue, Oct 13 - Tue, Oct 20
BWI
Baltimore Washington Intl. Thurgood Marshall
RUT
Rutland Southern Vermont Regional
$398 Roundtrip, found 18 hours ago
$398
Roundtrip
found 18 hours ago
Select Delta flight, departing Tue, Oct 13 from Baltimore Washington Intl. Thurgood Marshall to Rutland Southern Vermont Regional, returning Tue, Oct 20, priced at $398 found 18 hours ago
American Airlines
Tue, Sep 22 - Tue, Oct 6
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$474 Roundtrip, found 3 days ago
$474
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 22 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Oct 6, priced at $474 found 3 days ago
American Airlines
Tue, Sep 22 - Tue, Oct 6
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$480 Roundtrip, found 3 days ago
$480
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 22 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Oct 6, priced at $480 found 3 days ago
American Airlines
Tue, Sep 22 - Sat, Oct 3
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$484 Roundtrip, found 3 days ago
$484
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 22 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Oct 3, priced at $484 found 3 days ago
American Airlines
Tue, Sep 22 - Tue, Oct 6
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$490 Roundtrip, found 3 days ago
$490
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 22 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Oct 6, priced at $490 found 3 days ago
American Airlines
Wed, Sep 23 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$494 Roundtrip, found 3 days ago
$494
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Sep 23 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $494 found 3 days ago
United
Wed, Sep 23 - Fri, Oct 2
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$499 Roundtrip, found 3 days ago
$499
Roundtrip
found 3 days ago
Select United flight, departing Wed, Sep 23 from San Diego Intl. to Rutland Southern Vermont Regional, returning Fri, Oct 2, priced at $499 found 3 days ago
American Airlines
Tue, Sep 22 - Tue, Oct 6
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$501 Roundtrip, found 3 days ago
$501
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 22 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Oct 6, priced at $501 found 3 days ago
American Airlines
Tue, Sep 22 - Mon, Oct 5
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$504 Roundtrip, found 3 days ago
$504
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 22 from San Diego Intl. to Rutland Southern Vermont Regional, returning Mon, Oct 5, priced at $504 found 3 days ago
Alaska Airlines
Thu, Sep 24 - Fri, Oct 2
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$504 Roundtrip, found 3 days ago
$504
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Sep 24 from San Diego Intl. to Rutland Southern Vermont Regional, returning Fri, Oct 2, priced at $504 found 3 days ago
United
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$506 Roundtrip, found 4 days ago
$506
Roundtrip
found 4 days ago
Select United flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $506 found 4 days ago
American Airlines
Sun, Sep 13 - Sat, Sep 26
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$660 Roundtrip, found 1 day ago
$660
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Sep 13 from McClellan-Palomar to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $660 found 1 day 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 August, 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 $237, 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 $237 right now, why wait?

Jamaica Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$237

Last Minute Hotel Deals in Jamaica

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! (860 reviews)
"Excellent amenities and perfect if you're traveling with a dog to VT. Rooms are very nice albeit a bit small and very low water pressure in the shower."

Reviewed on Aug 3, 2026

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Kimpton Taconic Hotel by IHG
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (945 reviews)
"Main Street Brattleboro so great, near Restaurants and entertainment. We saw a film downstairs, LPs and are Record player in Rooms!"

Reviewed on Aug 3, 2026

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Latchis 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! (657 reviews)
"Good place to stay, but not great."

Reviewed on Aug 4, 2026

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The Equinox Golf Resort & Spa
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 a free area shuttle. Popular attractions Mount Snow and Tumbleweed Ski ...
8.6/10 Excellent! (300 reviews)
"Host in restaurant let us stand at the host stand while he finished up his conversation with friends or regulars at bar until he realized to seat us. Took over 45 minutes to get a hamburger and pork slider sliders. Served to us at 9:00 pm sat at 8:10pm. Needed to hurry because they played the “Closing ..."

Reviewed on Aug 3, 2026

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Grand Summit Resort, A Vail Resorts Property
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 ...
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The Palmer House Resort, an Ascend Collection Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
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Hampton Inn Brattleboro
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.8/10 (32 reviews)
"This is a very tired motel. The sign says grand opening, but apparently their grand opening is sometime in the future! Tattered carpets, old drapery, no landscaping to speak of, the lounge area was filled with boxes. The check-in area needed a massive update. Breakfast seemed to have been an afterthought. ..."

Reviewed on Aug 3, 2026

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Colonial Motel
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! (1,007 reviews)
"Excellent place to stay. Entire building was very clean. I would recommend staying here. Dog friendly, never heard any noise."

Reviewed on Aug 5, 2026

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Hampton Inn and Suites Manchester
See all 2,583 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.