Hip Strip Holidays

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Photo by Sharon Evans

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    Save up to NZ$2,400 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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Price found within the past 48 hours. Click for updated prices.
  • 3 bars/lounges, swim-up bar, poolside bar, beach bar
    Jul 13 - Jul 20

    Sunset at the Palms Resort - Adults Only - All Inclusive + Flight

    Negril
    7 nights
    4.5 star property
    9.2/10 - Wonderful (1,000 reviews)
    "Very relaxing and tropical getaway great for a good relaxing vacation"
    Reviewed May 31, 2026
    Return • Montreal (YUL) - Kingston (KIN)
    YUL - KIN • 1 stop KIN - YUL • 1 stop
    NZ$7,355
    NZ$3,307
    per traveller
    found 2 hours ago
    Sunset at the Palms Resort - Adults Only - All Inclusive
  • View from room
    Jul 13 - Jul 20

    Excellence Oyster Bay - Adults Only All Inclusive + Flight

    Falmouth
    7 nights
    5.0 star property
    9.2/10 - Wonderful (1,333 reviews)
    "My wife and I had an amazing stay. The property was beautiful, clean, and well maintained. Our room was spotless and comfortable, with great views and everything we needed for a relaxing vacation. The beach was absolutely stunning, with crystal-clear water and plenty of space to relax. What really stood out was the staff. Everyone was friendly, welcoming, and went out of their way to make sure we had a great experience. The restaurants offered a good variety of food, and the service throughout..."
    Reviewed June 2, 2026
    Return • Montreal (YUL) - Kingston (KIN)
    YUL - KIN • 1 stop KIN - YUL • 1 stop
    NZ$8,939
    NZ$4,463
    per traveller
    found 2 hours ago
    Excellence Oyster Bay - Adults Only All Inclusive
  • Exterior
    Jul 13 - Jul 20

    The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive + Flight

    Falmouth
    7 nights
    5.0 star property
    10/10 - Exceptional (2 reviews)
    "Excellent Resort, especially all the excellence club amenities"
    Reviewed May 1, 2025
    Return • Montreal (YUL) - Kingston (KIN)
    YUL - KIN • 1 stop KIN - YUL • 1 stop
    NZ$27,311
    NZ$14,641
    per traveller
    found 2 hours ago
    The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive
  • Exterior
    Jul 13 - Jul 20

    The Signature Level At Grand Palladium Lady Hamilton Resort & Spa + Flight

    Lucea
    7 nights
    5.0 star property
    8.6/10 - Excellent (157 reviews)
    "Had an awesome time with my family, highly recommend!"
    Reviewed May 21, 2026
    Return • Montreal (YUL) - Kingston (KIN)
    YUL - KIN • 1 stop KIN - YUL • 1 stop
    Save 100% on your flight
    NZ$7,199
    NZ$3,891
    per traveller
    found 2 hours ago
    The Signature Level At Grand Palladium Lady Hamilton Resort & Spa
  • Aerial view
    Jul 13 - Jul 20

    Grand Palladium Jamaica Resort & Spa All Inclusive + Flight

    Lucea
    7 nights
    5.0 star property
    8.0/10 - Very good (1,539 reviews)
    "Expansive and grand looking property - lovely pool with waterfalls and very helpful and cheerful staff with towels etc. Multiple beach areas to hang out but wish the beaches were swept in the mornings. Also would be nice if we were told about all of the amenities upon arrival such as beach area with the water sport activities - wasn’t aware until day before departure. An information booklet in the rooms would have been helpful. Unfortunately, the area where my room is located had an awful..."
    Reviewed June 1, 2026
    Return • Montreal (YUL) - Kingston (KIN)
    YUL - KIN • 1 stop KIN - YUL • 1 stop
    Save 100% on your flight
    NZ$7,316
    NZ$4,088
    per traveller
    found 2 hours ago
    Grand Palladium Jamaica Resort & Spa All Inclusive

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$430 per night from 22 June to 23 June
NZ$430
22 June - 23 June
includes taxes & fees
8.2/10 Very Good! (1,805 reviews)
"I’ve stayed here 4 times and still very happy! Pleaseeeeeeeee however keep the AC low ! I was sweating up a storm at night !! ( you can adjust it but you’d have to keep adjusting it throughout the night )"

Reviewed on 2 June 2026

Deja Resort All Inclusive
Hotel 39 Jamaica

Hotel 39 Jamaica

4.5 out of 5
39 Jimmy Cliff Boulevard Montego Bay
The price is NZ$301 per night from 22 June to 23 June
NZ$301
22 June - 23 June
includes taxes & fees
8.6/10 Excellent! (713 reviews)
"I love it here the staff was amazing the breakfast the front desk was top tier one of my best stays ever"

Reviewed on 1 June 2026

Hotel 39 Jamaica
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 NZ$1,059 per night from 10 June to 11 June
NZ$1,059
10 June - 11 June
includes taxes & fees
9.4/10 Exceptional! (2,085 reviews)
"I enjoyed the property, the food was good and accommodation was excellent and clean. I loved the art decor throughout the resort displaying Jamaica culture. The staff were friendly and attentive. The resort lacked night time entertainment. I would have loved to see beach parties and parties on the ..."

Reviewed on 2 June 2026

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
See all 1,568 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$58
per adult
88% of travellers recommend
Club Mobay VIP Airport Lounge Service
Luminous Lagoon Experience

Luminous Lagoon Experience with Rum Punch & Transportation

NZ$119
per adult
Luminous Lagoon Experience with Rum Punch & Transportation
Jamwest Adventure Park

Jamwest Adventure Park

NZ$159
per adult
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.