Deals on vacations and trips to Jamaica

Save when you book Jamaica package deals

Choose two or more items and save on your trip:

Jamaica flight + hotel vacation packages

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

Mountaineer Inn

2 out of 5
per person
Jul 25 - Jul 28
found 5 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Springfield (VSF)
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and express check-in are also on offer.
The Shire Woodstock

The Shire Woodstock

3 out of 5
per person
Jul 26 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) 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.
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
per person
Jul 25 - Jul 28
found 5 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Springfield (VSF)
Ski-in/ski-out access and an indoor pool are featured at this smoke-free aparthotel. Enjoy the hot tub and perks like free self parking and free WiFi. Express check-out, laundry facilities, and barbecue grills are also on offer.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
per person
Jul 25 - Jul 28
found 5 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Springfield (VSF)
This smoke-free hotel features ski-in/ski-out access, a full-service spa, and 2 restaurants. 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.
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
per person
Jul 25 - Jul 28
found 5 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Springfield (VSF)
Ski-in/ski-out access and an outdoor pool are featured at this smoke-free aparthotel. Enjoy the indoor pool and perks like free self parking and free WiFi. A gym, a hot tub, and a sauna are also on offer.

Top Jamaica hotels deals

Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Free Cancellation
Reserve now, pay when you stay
Get rates
This smoke-free motel features a full-service spa, 2 indoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Hot Tub
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Free Cancellation
Reserve now, pay when you stay
Get rates
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
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road, Brattleboro, VT
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.
Pool
Hot Tub
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St., Manchester, VT
Free Cancellation
Get rates
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
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St, Manchester Center, VT
Get rates
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
Don't see what you're looking for?
See all available properties in Jamaica
View all properties
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.

Jamaica State Park

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 Dam

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.

Ball Mountain State Park

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 $563. 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.

Photos of local treasures

Browse Jamaica vacation photos for more inspiration

Jamaica
Photo by Darrell Bumbala
Photo by Darrell Bumbala