Jamaica Vacation Packages 2026 from $1,079

Jamaica flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Shire Woodstock

$1,079

per person

Dec 15 - Dec 19

found 19 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.

Okemo Mountain Lodging by Vail Resorts

Clock Tower Base Area

$1,487

per person

Dec 15 - Dec 19

found 19 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

This vacation home features laundry facilities. Take advantage of the free self parking.

Winterplace at Okemo, A Vail Resorts Property

Clock Tower Base Area

$1,405

per person

Dec 15 - Dec 19

found 19 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

Ski-in/ski-out access and an indoor pool are featured at this smoke-free aparthotel. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like express check-out and laundry facilities.

Solitude Village at Okemo by Vail Resorts

Clock Tower Base Area

$1,282

per person

Dec 15 - Dec 19

found 19 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

This smoke-free aparthotel's ski-in/ski-out access and 2 hot tubs are some of the highlights. Enjoy the gym and perks like free self parking and free WiFi. A sauna is also provided.

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

$1,177

per person

Dec 15 - Dec 19

found 19 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

Ski-in/ski-out access, 2 restaurants, and 3 hot tubs are all featured at this smoke-free hotel. There's a free ski shuttle, and ski lessons, ski passes and ski storage are available on site. Bring the family and enjoy the mini golf, playground, and arcade/game room.

Top Jamaica hotels deals

Grand Summit Resort, A Vail Resorts Property

89 Grand Summit Way West Dover VT

Free Cancellation

$169 nightly

$186 total

Nov 1 - Nov 2

Total with taxes and fees

This smoke-free resort features ski-in/ski-out access, a full-service spa, and a restaurant. Enjoy the gym and perks like free WiFi and a free area shuttle. You'll appreciate the sauna, bar/lounge, and laundry facilities.

Colonial Motel

889 Putney Rd Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$93 total

Nov 1 - Nov 2

Total with taxes and fees

Free self parking is available and the motel's front desk is staffed around-the-clock. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden, a grocery/convenience store, and a lobby fireplace are also on offer.

Breakfast included

Pet friendly

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT

Free Cancellation

Reserve now, pay when you stay

$112 nightly

$123 total

Nov 1 - Nov 2

Total with taxes and fees

A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.

Pool

Breakfast included

Aspen At Manchester

5669 Main Street Manchester Center VT

Free Cancellation

Reserve now, pay when you stay

$145 nightly

$160 total

Oct 25 - Oct 26

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a lobby fireplace are also on offer.

Pool

Pet friendly

Latchis Hotel

50 Main Street Brattleboro VT

$183 nightly

$201 total

Oct 7 - Oct 8

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking and luggage storage are also offered on site.

Pet friendly

Parking included

Pointe at Castle Hill Resort

2940 State Route 103 Cavendish VT

$155 nightly

$168 total

Oct 21 - Oct 22

Total with taxes and fees

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Hot Tub

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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.

Stay near popular Jamaica attractions

Jamaica State Park

8.8/10 (5 reviews)

You can take time to visit Jamaica State Park during your travels to Jamaica. Amble around the area's parks or visit its monuments.

See properties

Frequently asked questions

How much are vacation packages to Jamaica?

Get ready to be pleasantly surprised — you can recharge your batteries in Jamaica for only $1,079. Here at Travelocity, we save you money and time with our fantastic vacation packages. With flights, hotels and tours all ready to be snapped up, what's holding you back?

How long should my Jamaica vacation be?

Many visitors pack their bags and see the sights of Jamaica for approximately 3 nights. That's a great guide, but it's not a rule of thumb. Whether you stay for a few days to see the big attractions or stick around to discover the lesser-known sights, an amazing getaway awaits.

Where can I get the best vacation package deals for Jamaica?

There are excellent Jamaica package deals to snap up with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties around the globe? Keep that in mind the next time you're ready to cross another destination off your must-see list.

Why should I purchase my Jamaica vacation package with Travelocity?

Nothing beats the feeling of knowing you've just picked up the best price available — that's our Price Match Guarantee. Add to that our incredibly broad range of destinations and 24/7 team of customer service professionals and you've got the formula for a stress-free vacation.

Can I save on my Jamaica car rental if I bundle it with a hotel or flight?

Combining your car, flight and hotel into a Jamaica vacation package is a surefire way to score the best deal. Plus, having your own car rental gives you the freedom to make your way to all those big sights you want to check out. Located 100 mi from Jamaica, Fenway Park is one attraction that should be on your itinerary. Fasten your seat belt and make a day trip of it.

Which airport is best for Jamaica?

For plenty of travelers, a trip to Jamaica means stepping off the plane at Albany Intl. Airport (ALB). This busy airport sits 60 mi southwest of the downtown area. You could also fly into Lebanon Municipal Airport (LEB) (45 mi away from central Jamaica) or Rutland Southern Vermont Regional Airport (RUT) (30 mi away from central Jamaica).

What is there to do in Jamaica?

You'll sense a certain magic in the air as you stroll through the streets of Jamaica. Jamaica State Park and Hot Glass Works are just a couple of attractions that lure visitors to this fantastic city, so put them at the top of your to-do list.

Where should I stay when visiting Jamaica?

If you're searching for a place to base yourself, check out the Three Mountain Inn. It's the top pick for many travelers.