Hip Strip Vacation Packages

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Top Holiday Package Deals in Hip Strip

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

Retreat Plantation House

3 out of 5
Price was CA $3,211, price is now CA $1,558 per person
CA $1,558
per person
Sep 26 - Oct 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Montego Bay (MBJ)
10/10 Exceptional! (1 review)
Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
Price was CA $3,480, price is now CA $1,569 per person
CA $1,569
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

5 out of 5
Price was CA $21,305, price is now CA $10,126 per person
CA $10,126
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
Excellent Resort, especially all the excellence club amenities

Reviewed on May 1, 2025

Ocho Rios Villa at the Palms II

Ocho Rios Villa at the Palms II

3.5 out of 5
Price was CA $3,675, price is now CA $1,781 per person
CA $1,781
per person
Oct 24 - Oct 31
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Montego Bay (MBJ)
8.6/10 Excellent! (25 reviews)
Ocho Rios Villa at Coolshade X

Ocho Rios Villa at Coolshade X

3.5 out of 5
Price was CA $3,245, price is now CA $1,613 per person
CA $1,613
per person
Sep 25 - Oct 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Montego Bay (MBJ)
9.6/10 Exceptional! (5 reviews)

Where to stay in Hip Strip

Find the best Hip Strip areas and neighborhoods for the activities you enjoy most. Learn more about Hip Strip
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Ironshore

Though Ironshore might not have many top sights, you can venture to the surrounding area to see attractions like Blue Diamond Shopping Centre and SuperClubs Ironshore Golf and Country Club.

Find hotels in Ironshore

Hip Strip Hotel Deals

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

4 out of 5
7 Jimmy Cliff Blvd, Montego Bay, Saint James
Fully refundableReserve now, pay when you stay
The price is CA $493 per night from Sep 1 to Sep 2
CA $493
CA $573 total
Sep 1 - Sep 2
includes taxes & fees
9.4/10 Exceptional! (2,023 reviews)
"I would go back to S Hotel over and over again!"

Reviewed on Aug. 17, 2025

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
Deja Resort All Inclusive

Deja Resort All Inclusive

3.5 out of 5
92 Gloucester Avenue, Montego Bay, Saint James
Fully refundableReserve now, pay when you stay
The price is CA $227 per night from Sep 19 to Sep 20
CA $227
CA $269 total
Sep 19 - Sep 20
includes taxes & fees
7.8/10 Good! (1,336 reviews)
"Parking was horrible, but I don’t think there’s nothing they can do about it because this space is not big"

Reviewed on Aug. 17, 2025

Deja Resort All Inclusive
Grand Decameron Montego Beach, A Trademark All-Inclusive Resort

Grand Decameron Montego Beach, A Trademark All-Inclusive Resort

3.5 out of 5
2 Gloucester Avenue, Montego Bay, Saint James
The price is CA $238 per night from Aug 21 to Aug 22
CA $238
CA $268 total
Aug 21 - Aug 22
includes taxes & fees
6.4/10 (1,009 reviews)
"The property is beautiful"

Reviewed on Aug. 18, 2025

Grand Decameron Montego Beach, A Trademark All-Inclusive Resort
See all 1,567 properties in Hip Strip
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Hip Strip vacation package cost?
Create unforgettable memories with our Hip Strip vacation packages, which start from just CA $1,558. Select the hotels and flights that suit your travel plans. Then, add on a couple of activities or tours to cap off your unique escape.
How do I get a cheap travel package to Hip Strip?
You'll save loads of cash if you bundle your car rentals, flights and hotels into a Hip Strip vacation package. Sometimes cheap packages mean fewer choices. But not with Expedia. We offer over 550 air carriers and 1,000,000 hotels worldwide, which means you'll always have plenty of options to choose from. Want to save even more? Add some interesting activities to your package deal to unlock even bigger bargains! After all, travel is about more than just getting to your destination.
Where should I stay in Hip Strip?
If you love being in the thick of the action, stay close to Rocklands Bird Sanctuary. Many visitors book a hotel around this renowned attraction.
What are the top hotels in Hip Strip?
Get your vacation off to an excellent start by staying at Montego Bay Three - Bedroom Townhouse Near Beach With Pool And Free Airport Shuttle. It's one of most popular properties in Hip Strip. Another top option is Vacation And Relaxation.
How far in advance should I book my Hip Strip vacation?
Reward yourself with the widest variety and the lowest prices by booking your Hip Strip adventure nice and early. Airlines tend to publish flights around 12 months before departure, so secure your spot as soon as you can. That being said, Expedia is committed to giving you the best bargains around, so there's never a bad time to book your dream vacation!
What does an Expedia Hip Strip travel package include?
It all depends on what kind of getaway you're planning. Hip Strip travel deals can include flights, hotels and car rentals. You can mix and match to find the bundle that suits your needs. You can also add on experiences and activities after you've booked to get even bigger discounts.
What should I know before booking a Hip Strip travel package?
An Expedia travel package can be customized for your circumstances and is a simple way to make your hard-earned dollars stretch further. How much you include is completely up to you. Rental cars, hotels and flights — come up with a combination that suits your style.
Can I choose my airline with a Hip Strip Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You're in charge! We have more than 550 partner airlines around the world, so you have lots of choice when putting together your Hip Strip adventure.
If I'm not able to travel, can I cancel my Hip Strip vacation package?
We get that life sometimes gets in the way of your plans. If you've locked in a Hip Strip vacation package and have to amend or cancel it, we can help. It's always worth looking up our Customer Service Portal first for information. But in general, if you've booked your package within 24 hours, you may be able to cancel or amend your itinerary at no cost. If it's been more than 24 hours, your airline, hotel or car rental company may impose a charge.

Discover the most popular places to visit in Hip Strip

Doctor\'s Cave Beach showing a coastal town, tropical scenes and a beach

Doctor's Cave Beach

4.5/5(67 reviews)

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
Rose Hall Great House featuring a house and heritage architecture

Rose Hall Great House

4/5(16 reviews)

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

Rose Hall Great House
Montego Bay Cruise Ship Terminal

Montego Bay Cruise Ship Terminal

4/5(18 reviews)

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

Things to do

Montego Bay’s Night Life Clubbing: Lounge 27/27 | Pier 1 | Taboo

Montego Bay’s Night Life Clubbing: Lounge 27/27 | Pier 1 | Taboo

CA $136
per adult
Montego Bay’s Night Life Clubbing: Lounge 27/27 | Pier 1 | Taboo
Montego Bay: Parasailing and Jet Ski Combo

Montego Bay: Jet Car, Jet Ski and Parasailing

CA $284
per adult
Montego Bay: Jet Car, Jet Ski and Parasailing
Night Life Tour in Montego Bay with complimentary section

Night Life Tour in Montego Bay with complimentary section

CA $48
per adult
94% of travellers recommend
Night Life Tour in Montego Bay with complimentary section
See all activities in Montego Bay
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.