Hip Strip Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Hip Strip Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Caves
West End
$1,734
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Charlottesville (CHO) to Montego Bay (MBJ)
Book a stay at this business-friendly hotel in Negril. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Seven Mile Beach and Negril Cliffs are located nearby.
Villa Sweet Villa
$3,741
per person
Oct 4 - Oct 10
found 17 hours ago
Roundtrip non-stop flight included
Charlottesville (CHO) to Montego Bay (MBJ)
Book a stay at this beach villa in Montego Bay. Enjoy free WiFi, free parking, and private pools. Popular attractions Rose Hall Great House and Doctor's Cave Beach are located nearby.
Modern 4BR Hillside Villa Pool Beach Club Access
$6,523
per person
Oct 4 - Oct 10
found 17 hours ago
Roundtrip non-stop flight included
Charlottesville (CHO) to Montego Bay (MBJ)
Stay at this villa in Montego Bay. Enjoy free parking and a garden. Popular attractions Rose Hall Great House and The Shoppes at Rose Hall are located nearby.
Secluded 3BR Garden Villa Pool Ocean Views
$4,192
per person
Oct 4 - Oct 10
found 17 hours ago
Roundtrip non-stop flight included
Charlottesville (CHO) to Montego Bay (MBJ)
Stay at this villa in Sandy Bay. Enjoy free parking and a garden. Popular attraction Chukka Ocean Outpost at Sandy Bay is located nearby.
Tranquil 4BR Villa Pool Spa Resort Access
$6,905
per person
Oct 4 - Oct 10
found 17 hours ago
Roundtrip non-stop flight included
Charlottesville (CHO) to Montego Bay (MBJ)
Stay at this villa in Montego Bay. Enjoy free parking and a garden. Popular attractions Rose Hall Great House and Doctor's Cave Beach are located nearby.
Ocho Rios Villa at the Palms IV
$2,120
per person
Oct 4 - Oct 10
found 17 hours ago
Roundtrip non-stop flight included
Charlottesville (CHO) to Montego Bay (MBJ)
Book a stay at this golf villa in St. Ann's Bay. Enjoy free WiFi, free parking, and a golf course. Popular attractions Cranbrook Flower Forest and Priory Beach are located nearby.
We were greeted by Ms Kathy who took us on a tour of the villa. It was very nice and more than enough space for me and my 4 girls. The pool/clubhouse was very very nice. I was very skeptical of doing this online and this place did not disappoint. I will be returning! Big ups to Kathy!!!
Reviewed on Mar 23, 2018
Top Hotel Deals
Deja Resort All Inclusive
92 Gloucester Avenue Montego Bay Saint James
Book a stay at this beach property in Montego Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
7 Jimmy Cliff Blvd Montego Bay Saint James
Book a stay at this beach property in Montego Bay. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our ...
Toby's Resort
1 Kent Avenue Montego Bay Saint James
Stay at this hotel in Montego Bay. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in our reviews. ...
Hotel 39 Jamaica
39 Jimmy Cliff Boulevard Montego Bay
Book a stay at this luxury hotel in Montego Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Montego Bay Club Beach Resort
11 Queens Drive Montego Bay St.James
Stay at this aparthotel in Montego Bay. Enjoy free parking, a 24-hour front desk, and an airport shuttle (surcharge). Popular attractions Doctor's Cave Beach ...
Montego Bay Club Apartments
11 Queens Drive Montego Bay St. James Parish
Stay at this apartment in Montego Bay. Enjoy free WiFi, free parking, and an airport shuttle (surcharge). Popular attractions Doctor's Cave Beach and Walter ...
Polkerris Bed & Breakfast
13 Corniche Road Montego Bay Saint James
Stay at this B&B in Montego Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Hip Strip Vibe
46 Jimmy Cliff Boulevard Montego Bay St. James Parish
Stay at this guesthouse in Montego Bay. Enjoy free WiFi, housekeeping, and climate control. Popular attractions Doctor's Cave Beach and Walter Fletcher Beach ...
Ocean View Suit-Montego Bay Club Resort
11 Queens Dr Montego Bay
Book a stay at this beach apartment in Montego Bay. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Doctor's Cave Beach and Walter Fletcher ...
Hotel Riu Montego Bay - Adults Only - All Inclusive
Mahoe Bay, Ironshore Montego Bay Saint James
Book a stay at this beach property in Montego Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our ...
Hotel Riu Palace Aquarelle - All Inclusive
Falmouth Falmouth
Book a stay at this beach hotel in Falmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Hotel Riu Reggae - Adults Only - All Inclusive
Montego Bay Montego Bay
Book a stay at this beach property in Montego Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our ...
Iberostar Waves Rose Hall Beach - All Inclusive
Rose Hall Beach Main Road Montego Bay Saint James
Book a stay at this luxury property in Montego Bay. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms ...
Grand Palladium Jamaica Resort & Spa All Inclusive
The Point Lucea Hanover
Book a stay at this luxury resort in Lucea. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. ...
Grand Palladium Lady Hamilton Resort & Spa All Inclusive
The Point Lucea Hanover
Book a stay at this luxury resort in Lucea. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Oct 19 - Fri, Oct 30
JFK
John F. Kennedy Intl.
MBJ
Sir Donald Sangster Intl.
$318
Roundtrip
found 2 days ago
Mon, Oct 26 - Tue, Nov 10
EWR
Newark Liberty Intl. Airport
MBJ
Sir Donald Sangster Intl.
$318
Roundtrip
found 17 hours ago
Mon, Sep 21 - Thu, Oct 8
JFK
John F. Kennedy Intl.
MBJ
Sir Donald Sangster Intl.
$322
Roundtrip
found 2 days ago
Mon, Nov 2 - Thu, Nov 5
JFK
John F. Kennedy Intl.
MBJ
Sir Donald Sangster Intl.
$324
Roundtrip
found 4 days ago
Sat, Sep 19 - Mon, Sep 28
LGA
LaGuardia
MBJ
Sir Donald Sangster Intl.
$344
Roundtrip
found 1 day ago
Best points of interest in Montego Bay
- Doctor's Cave Beach Vacations
- Rose Hall Great House Vacations
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- Half Moon Golf Course Vacations
- Montego Bay Cruise Ship Terminal Vacations
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- Saint James Parish Church Vacations
- Montego Bay Marine Park Vacations
- Blue Diamond Shopping Centre Vacations
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More Types of Hotels
- Beach Hotels in Hip Strip
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- Hotels with Air Conditioning in Hip Strip
- Hotels with a Pool in Hip Strip
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- Family Hotels in Hip Strip
- Hotel with wifi in Hip Strip
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- Hotel with a Concierge in Hip Strip
- Resorts & Hotels with Spas in Hip Strip
- Hotels with smoking rooms in Hip Strip
- Hotels with Hot Tubs in Hip Strip
- Casinos in Hip Strip
- Hotels with Free Airport Shuttle in Hip Strip
- Scuba Diving in Hip Strip