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High Street Vacation Packages

High Street Flight + Hotel Packages

Prices and availability subject to change. Additional terms may apply.
Alamanda Cottage at Serenity

Alamanda Cottage at Serenity

3 out of 5
Save 100% on your flight
per person
Jun 17 - Jun 22
Roundtrip flight included
Newark (EWR) to Montego Bay (MBJ)
Stay at this 3-star business-friendly cottage in Montego Bay. Enjoy free WiFi, free parking, and private yards. Popular attractions Doctor's Cave Beach and Rose Hall Great House are located nearby. Discover genuine guest reviews for Alamanda Cottage at Serenity along with the latest prices and availability – book now.
Riu Palace Aquarelle - All Inclusive

Riu Palace Aquarelle - All Inclusive

4 out of 5
per person
May 27 - Jun 1
Roundtrip non-stop flight included
Baltimore (BWI) to Montego Bay (MBJ)
Stay at this 4-star beach hotel in Falmouth. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Martha Brae River and Luminous Lagoon are located nearby. Discover genuine guest reviews for Riu Palace Aquarelle - All Inclusive along with the latest prices and availability – book now.
Riu Montego Bay - Adults Only - All Inclusive

Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Save 100% on your flight
per person
May 26 - May 30
Roundtrip non-stop flight included
Baltimore (BWI) to Montego Bay (MBJ)
Stay at this 4-star beach property in Montego Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Doctor's Cave Beach and Rose Hall Great House are located nearby. Discover genuine guest reviews for Riu Montego Bay - Adults Only - All Inclusive along with the latest prices and availability – book now.
Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

4.5 out of 5
Save 100% on your flight
per person
May 31 - Jun 4
Roundtrip non-stop flight included
Baltimore (BWI) to Montego Bay (MBJ)
Stay at this 4.5-star luxury property in Negril. Enjoy free breakfast, free WiFi, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Seven Mile Beach and Hedonism II are located nearby. Discover genuine guest reviews for Sunset at the Palms Resort - Adults Only - All Inclusive along with the latest prices and availability – book now.
Azul Beach Resort Negril, Gourmet All Inclusive by Karisma

Azul Beach Resort Negril, Gourmet All Inclusive by Karisma

5 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 15
Roundtrip non-stop flight included
Dallas (DFW) to Montego Bay (MBJ)
Stay at this 5-star luxury property in Negril. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Seven Mile Beach and Hedonism II are located nearby. Discover genuine guest reviews for Azul Beach Resort Negril, Gourmet All Inclusive by Karisma along with the latest prices and availability – book now.
RIU Ocho Rios - All Inclusive

RIU Ocho Rios - All Inclusive

3.5 out of 5
Save 100% on your flight
per person
May 27 - Jun 1
Roundtrip non-stop flight included
Baltimore (BWI) to Montego Bay (MBJ)
Stay at this 3.5-star beach property in Ocho Rios. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Dunn's River Falls and Mystic Mountain are located nearby. Discover genuine guest reviews for RIU Ocho Rios - All Inclusive along with the latest prices and availability – book now.
Riu Palace Jamaica - Adults Only - All Inclusive

Riu Palace Jamaica - Adults Only - All Inclusive

4.5 out of 5
Save 100% on your flight
per person
May 27 - Jun 1
Roundtrip non-stop flight included
Baltimore (BWI) to Montego Bay (MBJ)
Stay at this 4.5-star luxury property in Montego Bay. Enjoy free breakfast, free WiFi, and 3 outdoor pools. Our guests praise the breakfast and the bar in our reviews. Popular attractions Doctor's Cave Beach and Rose Hall Great House are located nearby. Discover genuine guest reviews for Riu Palace Jamaica - Adults Only - All Inclusive along with the latest prices and availability – book now.
Ocean Eden Bay - Adults Only - All inclusive

Ocean Eden Bay - Adults Only - All inclusive

5 out of 5
Save 100% on your flight
per person
May 26 - May 30
Roundtrip non-stop flight included
Baltimore (BWI) to Montego Bay (MBJ)
Stay at this 5-star luxury property in Falmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the restaurant in our reviews. Popular attractions Burwood Beach and Blue Waters Beach Club are located nearby. Discover genuine guest reviews for Ocean Eden Bay - Adults Only - All inclusive along with the latest prices and availability – book now.
Riu Reggae - Adults Only - All Inclusive

Riu Reggae - Adults Only - All Inclusive

4 out of 5
Save 100% on your flight
per person
May 27 - Jun 1
Roundtrip non-stop flight included
Baltimore (BWI) to Montego Bay (MBJ)
Stay at this 4-star beach property in Montego Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Doctor's Cave Beach and Rose Hall Great House are located nearby. Discover genuine guest reviews for Riu Reggae - Adults Only - All Inclusive along with the latest prices and availability – book now.
The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

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

5 out of 5
per person
May 27 - Jun 1
Roundtrip non-stop flight included
Baltimore (BWI) to Montego Bay (MBJ)
Stay at this 5-star luxury property in Falmouth. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions Luminous Lagoon and Blue Waters Beach Club are located nearby. Discover genuine guest reviews for The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive along with the latest prices and availability – book now.
RIU Palace Tropical Bay - All Inclusive

RIU Palace Tropical Bay - All Inclusive

4 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 18
Roundtrip non-stop flight included
Dallas (DFW) to Montego Bay (MBJ)
Stay at this 4-star beach property in Negril. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Seven Mile Beach and Hedonism II are located nearby. Discover genuine guest reviews for RIU Palace Tropical Bay - All Inclusive along with the latest prices and availability – book now.
Excellence Oyster Bay - Adults Only All Inclusive

Excellence Oyster Bay - Adults Only All Inclusive

5 out of 5
Save 100% on your flight
per person
May 27 - Jun 1
Roundtrip non-stop flight included
Baltimore (BWI) to Montego Bay (MBJ)
Stay at this 5-star luxury property in Falmouth. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Luminous Lagoon and Blue Waters Beach Club are located nearby. Discover genuine guest reviews for Excellence Oyster Bay - Adults Only All Inclusive along with the latest prices and availability – book now.

3-4 Night Vacations in High Street

Prices and availability subject to change. Additional terms may apply.
Riu Montego Bay - Adults Only - All Inclusive

Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Save 100% on your flight
per person
May 26 - May 30
Roundtrip non-stop flight included
Baltimore (BWI) to Montego Bay (MBJ)
Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

4.5 out of 5
Save 100% on your flight
per person
Jun 8 - Jun 11
Roundtrip non-stop flight included
Baltimore (BWI) to Montego Bay (MBJ)
Riu Palace Aquarelle - All Inclusive

Riu Palace Aquarelle - All Inclusive

4 out of 5
Save 100% on your flight
per person
Jun 18 - Jun 21
Roundtrip non-stop flight included
Baltimore (BWI) to Montego Bay (MBJ)
Casa Marina Montego Bay at Seawind

Casa Marina Montego Bay at Seawind

3 out of 5
Save 100% on your flight
per person
May 26 - May 29
Roundtrip non-stop flight included
Philadelphia (PHL) to Montego Bay (MBJ)

5-7 Night Vacations in High Street

Prices and availability subject to change. Additional terms may apply.
Riu Montego Bay - Adults Only - All Inclusive

Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
per person
May 27 - Jun 1
Roundtrip non-stop flight included
Baltimore (BWI) to Montego Bay (MBJ)
Alamanda Cottage at Serenity

Alamanda Cottage at Serenity

3 out of 5
Save 100% on your flight
per person
Jun 17 - Jun 22
Roundtrip flight included
Newark (EWR) to Montego Bay (MBJ)
Riu Palace Aquarelle - All Inclusive

Riu Palace Aquarelle - All Inclusive

4 out of 5
per person
May 27 - Jun 1
Roundtrip non-stop flight included
Baltimore (BWI) to Montego Bay (MBJ)
Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

4.5 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 18
Roundtrip non-stop flight included
Dallas (DFW) to Montego Bay (MBJ)

High Street Last Minute Hotel Deals

Waterloo Guest House
Waterloo Guest House
2.5 out of 5
44 High Street, Black River, St. Elizabeth Parish
Stay at this hotel in Black River. Enjoy free WiFi, free parking, and breakfast. Popular attractions Black River Heritage Buildings and High Street are located ...
Waterloo Guest House
Idlers' Rest Beach Hotel
Idlers' Rest Beach Hotel
2.5 out of 5
Parottee Road, A2, Black River, Saint Elizabeth
Stay at this beach hotel in Black River. Enjoy a beach locale, breakfast, and onsite parking. Popular attractions Black River Heritage Buildings and High Street ...
Idlers' Rest Beach Hotel
Deano's Cottages
Deano's Cottages
4.5 out of 5
Lot 165 Fullerswood District, 165, Black River, St. Elizabeth Parish
Stay at this 4.5-star luxury cottage in Black River. Enjoy free WiFi, free parking, and breakfast. Popular attractions Parrotee Pond Mangroves and Black River ...
Deano's Cottages
Rafjam West
Rafjam West
3 out of 5
south Sea Park, lot 336, Whitehouse
Stay at this 3-star beach B&B in Whitehouse. Enjoy free breakfast, free WiFi, and free parking. Popular attraction Fonthill Nature Reserve is located nearby. ...
Rafjam West
Kassion Corner
Kassion Corner
3 out of 5
Petersville, Whitehouse, Westmoreland Parish
Stay at this 3-star guesthouse in Whitehouse. Enjoy free WiFi, free parking, and breakfast. Popular attractions Fonthill Nature Reserve and Peter Tosh Monument ...
Kassion Corner
Champagne Villa
Champagne Villa
3 out of 5
Lot 1 Kings Pen, Whitehouse, Westmoreland
Stay at this 3-star beach villa in Whitehouse. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Fonthill Nature Reserve and Peter Tosh ...
Champagne Villa
Sandals South Coast - ALL INCLUSIVE Couples Only
Sandals South Coast - ALL INCLUSIVE Couples Only
4.5 out of 5
A2, P.O. Box 5000, Whitehouse, Westmoreland
Stay at this 4.5-star luxury property in Whitehouse. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the room service in our reviews. Popular ...
Sandals South Coast - ALL INCLUSIVE Couples Only
Jakes
Jakes
3.5 out of 5
Calabash Bay - Treasure Beach, Treasure Beach, Saint Elizabeth
Stay at this 3.5-star beach resort in Treasure Beach. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
Jakes
See all 666 properties in High Street
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.

Book the perfect getaway to High Street

With Hotwire, booking your next trip to Jamaica is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to High Street while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar High Street flight and hotel package for as low as $875.

Living it up in Jamaica means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s High Street, Jamaica vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in High Street for some of the best accommodations and flight deals.

FAQs about cheap High Street packages:

How to get cheap vacation deals to High Street?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $60.

How much are High Street packages?

Vacation packages to High Street vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $875.

How to find cheap car rentals near High Street?

Hotwire partners with some of the most reliable car rental companies in Jamaica to bring you the best car rental deals in High Street for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to High Street now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to High Street right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

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