Greenwood Vacations from $974

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Your Greenwood Vacation

Book a Greenwood vacation package and get ready to experience the best of this lively city. Think about staying in the neighborhood of Hip Strip, which is good for coastal beaches, nightlife and bars and pubs. Every trip to Greenwood needs a well-thought-out itinerary. Fill yours with major attractions like Rose Hall Great House, Cinnamon Hill Golf Course and Rose Hall Great House. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Greenwood vacation is simple with Expedia.

The Latest Greenwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Alamanda Cottage at Serenity

Alamanda Cottage at Serenity

3 out of 5
Ironshore
Price was $2,542, price is now $974 per person
$974
per person
Feb 6 - Feb 12
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
No reviews
Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

4.5 out of 5
Price was $5,746, price is now $2,008 per person
$2,008
per person
Feb 6 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
9/10 Wonderful! (1,002 reviews)
It was definitely a great experience with friendly staff and great food highly recommended..

Reviewed on Nov 22, 2025

Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
Price was $2,804, price is now $1,144 per person
$1,144
per person
Jan 8 - Jan 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
Ocean Eden Bay - Adults Only - All inclusive

Ocean Eden Bay - Adults Only - All inclusive

5 out of 5
Price was $3,107, price is now $1,366 per person
$1,366
per person
Feb 7 - Feb 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Montego Bay (MBJ)
8.4/10 Very Good! (3,680 reviews)
The staff was amazing and treated me as a vip guest through of the most horrifying category 5 hurricanes the country has seen in over 100 years

Reviewed on Nov 15, 2025

Ocean Coral Spring - All Inclusive

Ocean Coral Spring - All Inclusive

5 out of 5
Price was $2,352, price is now $1,046 per person
$1,046
per person
Feb 16 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
8.4/10 Very Good! (3,949 reviews)
The staff is extremely friendly, the food is excellent, and the facilities are nice.

Reviewed on Nov 26, 2025

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Discover the most popular places to visit in Greenwood

Rose Hall Great House which includes heritage architecture and a house

Rose Hall Great House

Tour this grand English-style manor and former plantation, and discover its eerie history.

Rose Hall Great House
Doctor\'s Cave Beach featuring a beach, a coastal town and tropical scenes

Doctor's Cave Beach

White sand, bright blue water and a nearby bar make this beach the perfect spot for a relaxing in the beautiful Jamaican weather.

Doctor's Cave Beach
View from the ship

Montego Bay Cruise Ship Terminal

Explore the waterfront in Montego Bay with a trip to Montego Bay Cruise Ship Terminal. Amble around this relaxing area's beautiful beaches, or seek out the local tours.

Montego Bay Cruise Ship Terminal

What to do in Greenwood

Bamboo River Rafting On The Martha Brae

Bamboo River Rafting On The Martha Brae

$114
per traveler
90% of travellers recommend
Bamboo River Rafting On The Martha Brae
Adults Only Reggae Catamaran Cruise with Snorkeling & Drinks

Adults Only Reggae Catamaran Cruise with Snorkeling & Drinks

$125
per traveler
82% of travellers recommend
Adults Only Reggae Catamaran Cruise with Snorkeling & Drinks
Luminous Lagoon Experience

Luminous Lagoon Experience with Rum Punch & Transportation

$71
per adult
Luminous Lagoon Experience with Rum Punch & Transportation
See all activities in Greenwood

Greenwood Hotel Deals

Sunshine Lodge- Your Home Away From Home

Sunshine Lodge- Your Home Away From Home

4 out of 5
Belgrade Ave Montego Bay St. James Parish
7.4/10 Good! (3 reviews)
It was beautiful on the inside and had an amazing view of Montego Bay.

Reviewed on May 25, 2025

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Sunshine Lodge- Your Home Away From Home
Poinciana House

Poinciana House

2 out of 5
257 Poinciana Drive Montego Bay Montego Bay
$521 nightly
The price is $600 total per night from Nov 28 to Nov 29
$600 total
Nov 28 - Nov 29
Total with taxes and fees
Poinciana House
Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Mahoe Bay, Ironshore Montego Bay Saint James
8.4/10 Very Good! (5,134 reviews)
The staff was very polite abd courteous. Entertainment was on another level. Love it

Reviewed on Nov 16, 2025

Get rates
Hotel Riu Montego Bay - Adults Only - All Inclusive
See all 1,635 properties in Greenwood
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.

Find the Best Greenwood Vacation Packages

Greenwood Essential Information

Language
English
Currency
Jamaican dollars
Closest Airport
Sir Donald Sangster Intl. Airport (MBJ)
Max Temp Winter
80ºF
Max Temp Summer
85ºF
Top Sights
Doctors Cave Beach, Dead End Beach and Aquasol Beach Park

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Frequently asked questions

How much does a Greenwood vacation package cost?
You'll find cheap prices from $974 on Expedia for your Greenwood getaway. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Greenwood costs.
What are the cheapest months to go to Greenwood?
If you're hoping to score a cheap Greenwood vacation package, consider planning a trip in November, December and January. You're likely to find lower prices on accommodations and flights during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Greenwood?
The ideal duration of your Greenwood vacation depends on what you'd like to see and do. Generally, a few days to a week will give you time to hit all the leading sights and explore some hidden spots along the way.
How to find the best Greenwood package deals?
Bagging a cheap Greenwood package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget, add a couple of filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most economical Greenwood package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Greenwood vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking stays and flights individually. Better still, you can tailor your Greenwood escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Greenwood?
If you've got your Greenwood vacation dates finalized, book early to snap up some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Greenwood?

  1. Choose when to go: Check your calendar and get packing. Your preferred season and the available activities will also help you decide when to escape to Greenwood.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and meals to activities and airfares. Your hotel will probably be the largest expense during your trip to Greenwood.
  3. Discover Greenwood using our trip planning tool: Gain insights into the leading attractions and best properties for your trip to Greenwood. You can also save your favorite places, collaborate with your group and organize all your plans in one place.
  4. Decide how long to go away for: Now that you're more familiar with Greenwood, you can figure out the perfect length of your vacation. Pull together a rough itinerary and give yourself enough time to cover everything you want to see.
  5. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized Greenwood vacation package.
  6. Book any day trips or activities: Here's the fun part — locking in everything you want to see and do. Explore some of the exciting things to do in Greenwood and reserve your tickets in advance to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Greenwood vacation packages?
If you're anything like us, you love exploring new places but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Greenwood break across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.