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Jamaica

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Jamaica Flights as Low as $482

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

American Airlines
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$482 Roundtrip, found 2 days ago
$482
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $482 found 2 days ago
American Airlines
Sat, Sep 12 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$484 Roundtrip, found 1 hour ago
$484
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, Sep 12 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $484 found 1 hour ago
American Airlines
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$492 Roundtrip, found 2 days ago
$492
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $492 found 2 days ago
American Airlines
Mon, Sep 14 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$494 Roundtrip, found 1 day ago
$494
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $494 found 1 day ago
JetBlue Airways
Fri, Sep 11 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$502 Roundtrip, found 1 hour ago
$502
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Fri, Sep 11 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $502 found 1 hour ago
JetBlue Airways
Sat, Sep 12 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$503 Roundtrip, found 1 hour ago
$503
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Sat, Sep 12 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $503 found 1 hour ago
American Airlines
Sat, Sep 12 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$504 Roundtrip, found 1 hour ago
$504
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, Sep 12 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $504 found 1 hour ago
JetBlue Airways
Fri, Sep 11 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$506 Roundtrip, found 1 hour ago
$506
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Fri, Sep 11 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $506 found 1 hour ago
American Airlines
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$507 Roundtrip, found 2 days ago
$507
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $507 found 2 days ago
American Airlines
Sat, Sep 12 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$509 Roundtrip, found 1 hour ago
$509
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, Sep 12 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $509 found 1 hour ago
JetBlue Airways
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$511 Roundtrip, found 5 days ago
$511
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $511 found 5 days ago
JetBlue Airways
Fri, Sep 11 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$512 Roundtrip, found 2 days ago
$512
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Sep 11 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $512 found 2 days ago
JetBlue Airways
Sat, Sep 12 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$513 Roundtrip, found 1 hour ago
$513
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Sat, Sep 12 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $513 found 1 hour ago
United
Fri, Sep 11 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$514 Roundtrip, found 3 days ago
$514
Roundtrip
found 3 days ago
Select United flight, departing Fri, Sep 11 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $514 found 3 days ago
Delta
Sat, Sep 12 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$514 Roundtrip, found 14 hours ago
$514
Roundtrip
found 14 hours ago
Select Delta flight, departing Sat, Sep 12 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $514 found 14 hours ago
American Airlines
Sat, Sep 12 - Sat, Sep 26
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$598 Roundtrip, found 1 hour ago
$598
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, Sep 12 from McClellan-Palomar to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $598 found 1 hour 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 September, 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 $482, 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 $482 right now, why wait?

Jamaica Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$481

Last Minute Hotel Deals in Jamaica

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! (289 reviews)
"ac had to be turned back on every few hours. fridge broke three times and maintenance needed to bring new ones. pool and hot tub was closed even tho i specifically bought this booking because expedia said it was available. fire pit was nice and they had a great fourth of july celebration"

Reviewed on Jul 5, 2026

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Grand Summit Resort, A Vail Resorts Property
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! (854 reviews)
"The hotel was beautiful very tranquil. Lots to see and do. The staff were friendly and attentive to the guests. The food in the restaurant was amazing. The staff there were also friendly. It was so peaceful in the mountains and the hotel grounds were beautiful."

Reviewed on Jun 29, 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! (925 reviews)
"This hotel was the perfect landing place from a lot of traveling. It was clean, had unique historic ambience, and walkable to the whole town. Highly recommend!"

Reviewed on Jul 9, 2026

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Latchis Hotel
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 ...
5.4/10 (13 reviews)
"The bed was hard to sleep on, the outdoor pool was filled with dirt, the indoor pool/spa/massage area is dilapidated, and the continental breakfast offered the bare minimum. When using the shower, switching from tub to shower was a task in itself while the water pressure was weak"

Reviewed on Jul 6, 2026

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Colonial Motel
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 ...
8.2/10 Very Good! (1,006 reviews)
"I think all Hilton hotels have the same small and flat pillows which are not comfortable to sleep on but over all, It was okay. May be I just need to change my option in choosing where to stay. Breakfast is the same."

Reviewed on Jul 9, 2026

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Hampton Inn Brattleboro
The Manchester View

The Manchester View

2.5 out of 5
77 High Meadow Way & VT-7A 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 helpful staff and ...
9.4/10 Exceptional! (836 reviews)
"It appears the place was recently remodeled and repainted, and the facilities were clean. However, the room was situated close to the ground, so the bedding felt damp. Also, the bathroom door wouldn't close completely, and the curtains couldn't be fully drawn shut."

Reviewed on Jul 10, 2026

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The Manchester View
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 ...
8.2/10 Very Good! (964 reviews)
"They noticed i had a 13 year old daughter and 9 year old son in toe. The upgrade to a suíte was complimentary and close to the pool. Definitely suggest this place. Breakfast was good and everything is close. We really enjoyed our stay."

Reviewed on Jul 8, 2026

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The Palmer House Resort, an Ascend Collection Hotel
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,003 reviews)
"It would probably have a better review if the power had stayed on. I realize it wasn’t their fault, but the power went off and it was out for about 12 hours."

Reviewed on Jul 5, 2026

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The Putney Inn
See all 2,619 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.