Hip Strip Vacation Packages

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  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Holiday Package Deals in Hip Strip

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

Silver Creek Resort

3.5 out of 5
Price was CA $4,476, price is now CA $840 per person
CA $840
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Montego Bay (MBJ)
7/10 Good! (51 reviews)
The only concern we had was that there is no restaurants within walking distance,

Reviewed on May 20, 2024

2 Bdrm Apartment at Runaway Bay

2 Bdrm Apartment at Runaway Bay

3.5 out of 5
Price was CA $2,916, price is now CA $1,523 per person
CA $1,523
per person
Jun 12 - Jun 19
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Montego Bay (MBJ)
No reviews
Richmond Villa Rental Management

Richmond Villa Rental Management

3.5 out of 5
Price was CA $2,829, price is now CA $1,525 per person
CA $1,525
per person
Jun 10 - Jun 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
6/10 (2 reviews)
Property met out expectations. Close to the pool. Kid friendly. Great place to have a relaxintion vacation.

Reviewed on Jan 8, 2024

Ocho Rios Villa at Coolshade IX

Ocho Rios Villa at Coolshade IX

3.5 out of 5
Price was CA $3,229, price is now CA $1,759 per person
CA $1,759
per person
Jun 18 - Jun 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
No reviews
Ocho Rios TaylorMade Vacation Villas

Ocho Rios TaylorMade Vacation Villas

3.5 out of 5
Price was CA $2,980, price is now CA $1,632 per person
CA $1,632
per person
May 16 - May 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Montego Bay (MBJ)
8.4/10 Very Good! (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
Panoramic aerial view of the wonderful caribbean beach resort on Jamaica, Montego Bay, Rose Hall Suites, Grand Rose Hall Suites, Iberostar

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

Deja Resort All Inclusive

Deja Resort All Inclusive

3.5 out of 5
92 Gloucester Avenue Montego Bay Saint James
The price is CA $272 per night from Apr 29 to Apr 30
CA $272
CA $321 total
Apr 29 - Apr 30
includes taxes & fees
8/10 Very Good! (1,685 reviews)
Room needed upgraded, Breakfast was good, staff was good My room had limited beach view

Reviewed on Apr 10, 2026

Deja Resort All Inclusive
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 $714 per night from May 5 to May 6
CA $714
CA $826 total
May 5 - May 6
includes taxes & fees
9.4/10 Exceptional! (2,078 reviews)
Check-in took a bit longer than expected, small little mishap with my room but it was resolve immediately. I must say eveything else was PERFECT! The property was clean, my room was beautiful and clean, the staff were amazing everyone was so friendly. The daily food of choice was always on point. ...

Reviewed on Apr 9, 2026

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
Hotel 39 Jamaica

Hotel 39 Jamaica

4.5 out of 5
39 Jimmy Cliff Boulevard Montego Bay
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Apr 12 to Apr 13
CA $161
CA $191 total
Apr 12 - Apr 13
includes taxes & fees
8.4/10 Very Good! (575 reviews)
Could improve somewhat.

Reviewed on Apr 10, 2026

Hotel 39 Jamaica
See all 1,572 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 $840. 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

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
Rose Hall Great House

Rose Hall Great House

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

Rose Hall Great House
Mein Schiff 6 Cruise Ship docked beyond large ocean rocks in Montego Bay, Jamaica. Mountains in background landscape.

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

Things to do

Bamboo Rafting Adventure with Limestone Massage from Montego Bay

Bamboo Rafting Adventure with Limestone Massage from Montego Bay

CA $66
per adult
88% of travellers recommend
Bamboo Rafting Adventure with Limestone Massage from Montego Bay
Adults Only Reggae Catamaran Cruise with Snorkeling & Drinks

Adults Only Reggae Catamaran Cruise with Snorkeling & Drinks

CA $172
per traveller
86% of travellers recommend
Adults Only Reggae Catamaran Cruise with Snorkeling & Drinks
Bamboo River Rafting On The Martha Brae

Bamboo River Rafting On The Martha Brae

CA $156
per traveller
92% of travellers recommend
Bamboo River Rafting On The Martha Brae
See all activities in Montego Bay

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.