Hip Strip Vacation Packages

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  • Plan, book, travel with confidence

  • 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.
Ocho Rios Ocean View Villa at The Palms

Ocho Rios Ocean View Villa at The Palms

4 out of 5
Price was CA $2,684, price is now CA $1,365 per person
CA $1,365
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
8.6/10 Excellent! (9 reviews)
Clean, great customer service. Most importantly we felt safe. Would definitely stay again and again!!

Reviewed on Oct 10, 2024

Ocho Rios Villa at Coolshade X

Ocho Rios Villa at Coolshade X

3.5 out of 5
Price was CA $2,838, price is now CA $1,426 per person
CA $1,426
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
9.6/10 Exceptional! (5 reviews)
Ocho Rios Villa at the Palms V

Ocho Rios Villa at the Palms V

3 out of 5
Price was CA $2,921, price is now CA $1,501 per person
CA $1,501
per person
Jun 8 - Jun 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Montego Bay (MBJ)
No reviews
Ocho Rios Villa at Coolshade IX

Ocho Rios Villa at Coolshade IX

3.5 out of 5
Price was CA $3,122, price is now CA $1,626 per person
CA $1,626
per person
Jun 13 - Jun 20
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Montego Bay (MBJ)
No reviews
Ocho Rios Villa at Coolshade IV

Ocho Rios Villa at Coolshade IV

3.5 out of 5
Price was CA $2,791, price is now CA $1,456 per person
CA $1,456
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
9.4/10 Exceptional! (10 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 $273 per night from Apr 22 to Apr 23
CA $273
CA $322 total
Apr 22 - Apr 23
includes taxes & fees
8/10 Very Good! (1,674 reviews)
The staff was very nice and friendly.

Reviewed on Apr 7, 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
The price is CA $716 per night from May 5 to May 6
CA $716
CA $829 total
May 5 - May 6
includes taxes & fees
9.4/10 Exceptional! (2,080 reviews)
Great views, pool and beach. Staff was super attentive and friendly. Food and entertainment was exceptional. The common areas could be a little cleaner and better maintained.

Reviewed on Apr 7, 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
The price is CA $162 per night from Apr 13 to Apr 14
CA $162
CA $192 total
Apr 13 - Apr 14
includes taxes & fees
8.4/10 Very Good! (570 reviews)
The staff here are AMAZING Twitta , Ojay,Monique made my Jamaica trip unforgettable hotel was affordable clean and safe to stay at will be staying here again

Reviewed on Apr 7, 2026

Hotel 39 Jamaica
See all 1,580 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 $1,365. 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

4.5/5(69 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

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

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

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

Explore a world of travel with Expedia

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