Hip Strip Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Sharon Evans

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
Fully refundableReserve now, pay when you stay
The price is ₩316,618 per night from Mar 31 to Apr 1
₩316,618
₩373,410 total
Mar 31 - Apr 1
includes taxes & fees
8/10 Very Good! (1,611 reviews)
Awesome beach access and very helpful/friendly front desk staff

Reviewed on Mar 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
Fully refundableReserve now, pay when you stay
The price is ₩766,273 per night from Apr 6 to Apr 7
₩766,273
₩887,151 total
Apr 6 - Apr 7
includes taxes & fees
9.4/10 Exceptional! (2,133 reviews)
Clean room, clean property and amazing service

Reviewed on Mar 6, 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
8.4/10 Very Good! (528 reviews)
No ocean view no information about breakfast times or pool area. Problems with machine to make payment

Reviewed on Mar 5, 2026

Get rates
Hotel 39 Jamaica
See all 1,560 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 vacation package cost?
Create unforgettable memories with our Hip Strip vacation 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 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 featuring a beach, a coastal town and tropical scenes

Doctor's Cave Beach

4.5/5(508 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
Sam Sharpe Square featuring a square or plaza and a statue or sculpture

Sam Sharpe Square

4/5(198 reviews)

This bustling central square with quaint cobblestone streets offers history and colorful Georgian architecture.

Sam Sharpe Square

Montego Bay Convention Centre

4/5(217 reviews)

Learn about the events happening at Montego Bay Convention Centre during your trip to Montego Bay. Amble around this relaxing area's beautiful beaches, or seek out the golf courses.

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