Jamaica Vacation Packages 2026/2026 from $560

Jamaica flight + hotel vacation packages

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

The Shire Woodstock

$560

per person

Feb 25 - Feb 27

found 1 day ago

Roundtrip flight included

Buffalo (BUF) 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.

Woodstock Inn & Resort

$820

per person

Feb 25 - Feb 27

found 1 day ago

Roundtrip flight included

Buffalo (BUF) to Springfield (VSF)

This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free WiFi. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 hot tubs and indoor pool.

Fat Sheep Farm & Cabins

$593

per person

Feb 25 - Feb 27

found 1 day ago

Roundtrip flight included

Buffalo (BUF) to Springfield (VSF)

This farm stay doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A terrace, a garden, and a picnic area are also on offer.

Lincoln Inn & Gallery

West Woodstock

$619

per person

Feb 25 - Feb 27

found 1 day ago

Roundtrip flight included

Buffalo (BUF) to Springfield (VSF)

This inn doesn't skimp on freebies - guests receive free WiFi and free self parking. A fireplace in the lobby and a picnic area are also provided.

The Vesper

$592

per person

Feb 25 - Feb 27

found 1 day ago

Roundtrip flight included

Buffalo (BUF) to Springfield (VSF)

This bed & breakfast doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A virtual front desk are provided for your convenience.

Top Jamaica hotels deals

The Equinox Golf Resort & Spa

3567 Main Street Route 7A Manchester VT

Free Cancellation

Reserve now, pay when you stay

$218 nightly

$240 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.

Pool

Hot Tub

Kimpton Taconic Hotel by IHG

3835 Main St. Manchester VT

Free Cancellation

$186 nightly

$205 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.

Pool

Pet friendly

Pointe at Castle Hill Resort

2940 State Route 103 Cavendish VT

$146 nightly

$159 total

Dec 17 - Dec 18

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

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$140 total

Dec 14 - Dec 15

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

The Palmer House Resort, an Ascend Collection Hotel

5383 Main St Manchester Center VT

Free Cancellation

$122 nightly

$134 total

Dec 14 - Dec 15

Total with taxes and fees

This smoke-free hotel features a golf course, 2 outdoor tennis courts, and a restaurant. Enjoy the indoor pool and free perks like continental breakfast and free self parking. You'll appreciate the seasonal outdoor pool, bar/lounge, and free newspapers.

Pool

Hot Tub

The Covered Bridge Inn

1043 Putney Road Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$79 nightly

$87 total

Dec 11 - Dec 12

Total with taxes and fees

Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.

Parking included

Free WiFi

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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.

Popular places to visit

Jamaica State Park

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

Ball Mountain Dam

Learn about the local history of Jamaica when you take a trip to Ball Mountain Dam. Discover the mountain views in this quaint area, or enjoy its ski slopes.

Ball Mountain State Park

Enjoy a trip to Ball Mountain State Park and popular activities like skiing in Jamaica. Discover the mountain views in this quaint area.

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 $560. 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.