Hip Strip Holidays

Photo by Sharon Evans

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

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 Whitter Village are two attractions nearby that you can check out.

Find hotels in Ironshore

Top hotels in Hip Strip

Deja Resort All Inclusive

Deja Resort All Inclusive

3.5 out of 5
92 Gloucester Avenue Montego Bay Saint James
The price is S$325 per night from 14 Jun to 15 Jun
S$325
14 Jun - 15 Jun
includes taxes & fees
8.2/10 Very Good! (1,823 reviews)
"The value is outstanding....alcohol is excellent (drinks on the strip are expensive)...the room is a motel 6...but bathroom very comfortable...we don't stay in the room a lot..AC was solid..beach was beautiful and clean...staff was not rude but not happy...entertainment was solid in the bar...the ..."

Reviewed on 9 Jun, 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 S$809 per night from 24 Jun to 25 Jun
S$809
24 Jun - 25 Jun
includes taxes & fees
9.4/10 Exceptional! (2,105 reviews)
"Clean room"

Reviewed on 7 Jun, 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 S$230 per night from 22 Jun to 23 Jun
S$230
22 Jun - 23 Jun
includes taxes & fees
8.6/10 Excellent! (730 reviews)
"there was so many limitations and constraints about making substitutions or requests"

Reviewed on 8 Jun, 2026

Hotel 39 Jamaica
See all 1,569 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.

Popular places to visit

Rose Hall Great House

Rose Hall Great House

This English-style plantation house conceals centuries of dark secrets beneath the bright Caribbean sun.

Rose Hall Great House

Half Moon Golf Course

Enjoy a round of golf in Montego Bay at Half Moon Golf Course. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

Half Moon Golf Course

Westgate Shopping Centre

You can browse for the perfect souvenirs at Westgate Shopping Centre during your visit to Montego Bay. Wander the beautiful beaches or discover the area's beautiful sunsets.

Westgate Shopping Centre

Things to do

Adults Only Reggae Catamaran Cruise with Snorkeling & Drinks

Adults Only Reggae Catamaran Cruise with Snorkeling & Drinks

S$158
per traveller
86% of travellers recommend
Adults Only Reggae Catamaran Cruise with Snorkeling & Drinks
ATV, Bamboo Rafting and Negril Ricks Cafe from Montego Bay

ATV, Bamboo Rafting and Negril Ricks Cafe from Montego Bay

S$102
per adult
90% of travellers recommend
ATV, Bamboo Rafting and Negril Ricks Cafe from Montego Bay
Bamboo River Rafting On The Martha Brae

Bamboo River Rafting On The Martha Brae

S$144
per traveller
92% of travellers recommend
Bamboo River Rafting On The Martha Brae
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.