Hip Strip Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Sharon Evans

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  • Better together

    Save up to NZ$616 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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Our guide on 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

Ironshore might not have many top sights, but Blue Diamond Shopping Centre and SuperClubs Ironshore Golf and Country Club are two attractions nearby that you can check out.

Find hotels in Ironshore

Our pick of the best Hip Strip Hotel Deals

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 NZ$393 per night from 20 May to 21 May
NZ$393
20 May - 21 May
includes taxes & fees
8/10 Very Good! (1,702 reviews)
Dinning staff is excellent! Only one person doing the grill needs customer service training…, and you know who he is!!! Attitude towards Jamaican visitors STINK!

Reviewed on 18 Apr 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 NZ$885 per night from 5 May to 6 May
NZ$885
5 May - 6 May
includes taxes & fees
9.4/10 Exceptional! (2,077 reviews)
Staff was excellent

Reviewed on 18 Apr 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 NZ$230 per night from 23 Apr to 24 Apr
NZ$230
23 Apr - 24 Apr
includes taxes & fees
8.4/10 Very Good! (591 reviews)
Breakfast was amazing and the wait staff phenomenal.

Reviewed on 16 Apr 2026

Hotel 39 Jamaica
See all 1,575 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.

Frequently asked questions

How much does a Hip Strip holiday package cost?
Create unforgettable memories with our Hip Strip holiday packages, which start from just . 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 holiday 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 holiday 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 Holiday And Relaxation.
How far in advance should I book my Hip Strip holiday?
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 holiday!
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 holiday package?
Yes — that's the beauty of an Expedia holiday 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 holiday package?
We get that life sometimes gets in the way of your plans. If you've locked in a Hip Strip holiday 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

This exceptionally pretty beach helped kick-start the popularity of Montego Bay for tourists. One look at its tropical paradise perfection, and you'll see why.

Doctor's Cave Beach
Freeport Peninsula

Freeport Peninsula

Explore the great outdoors at Freeport Peninsula and enjoy the beautiful sunsets during your trip to Montego Bay. Discover the area's entertainment choices or seek out its local tours.

Freeport Peninsula

Blue Diamond Shopping Centre

During your trip to Montego Bay, you can browse for the perfect souvenirs at Blue Diamond Shopping Centre. Discover the beautiful sunsets and top-notch restaurants in this romantic area.

Blue Diamond Shopping Centre

Activities

Club Mobay VIP Airport Lounge & Fast-Track Service

Club Mobay VIP Airport Lounge Service

NZ$59
per adult
88% of travellers recommend
Club Mobay VIP Airport Lounge Service
Bamboo Rafting Adventure with Limestone Massage from Montego Bay

Bamboo Rafting Adventure with Limestone Massage from Montego Bay

NZ$83
per adult
88% of travellers recommend
Bamboo Rafting Adventure with Limestone Massage from Montego Bay
Jamwest Adventure Park

Jamwest Adventure Park

NZ$162
per adult
72% of travellers recommend
Jamwest Adventure Park
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.