Deals on vacations and trips to Middlesex

Save when you book Middlesex package deals

Choose two or more items and save on your trip:

Middlesex flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Alamanda Cottage at Serenity

Alamanda Cottage at Serenity

3 out of 5
Ironshore
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Montego Bay (MBJ)
An outdoor pool, free self parking, and laundry facilities are featured at this cottage. Luggage storage and a virtual front desk are also provided.
Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

4 out of 5
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
This all-inclusive resort features a private beach, free water park access, and a full-service spa. Relax with beach cabanas, sun loungers, and beach umbrellas. Families will appreciate the waterslide and convenience store.
Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

4.5 out of 5
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Montego Bay (MBJ)
This all-inclusive resort features free water park access, a full-service spa, and 9 restaurants. Relax with beach cabanas, sun loungers, and beach umbrellas. Bring the family and enjoy the free kid's club, children's pool, and waterslide.
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
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
A full-service spa, 11 restaurants, and 2 outdoor pools are all featured at this all-inclusive property. Enjoy the 3 hot tubs and perks like free buffet breakfast and a free airport shuttle. 3 poolside bars and 10 bars/lounges are featured at this property, along with a 24-hour gym.
Ocho Rios Villa at the Palms V

Ocho Rios Villa at the Palms V

3 out of 5
per person
Sep 5 - Sep 12
found 10 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Montego Bay (MBJ)
A golf course and an outdoor pool are featured at this smoke-free villa. Traveling on business? Take advantage of the free WiFi in public areas and airport shuttle. Enjoy the 24-hour gym and perks like free self parking.

Top Middlesex hotels deals

Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

4.5 out of 5
Industry Cove, Green Island, Hanover
Get rates
This all-inclusive resort features free water park access, a full-service spa, and 9 restaurants. Relax with beach cabanas, sun loungers, and beach umbrellas. Bring the family and enjoy the free kid's club, children's pool, and waterslide.
Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

4 out of 5
Industry Cove, Green Island, Hanover
Get rates
This all-inclusive resort features a private beach, free water park access, and a full-service spa. Relax with beach cabanas, sun loungers, and beach umbrellas. Families will appreciate the waterslide and convenience store.
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
Free Cancellation
Reserve now, pay when you stay
Get rates
A full-service spa, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free property. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.
Deja Resort All Inclusive

Deja Resort All Inclusive

3.5 out of 5
92 Gloucester Avenue, Montego Bay, Saint James
Free Cancellation
Reserve now, pay when you stay
Get rates
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free property. Families will appreciate the onsite laundry facilities, kid-friendly dining, and free supervised childcare. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and free self parking.
SeaGarden Beach Resort - All Inclusive

SeaGarden Beach Resort - All Inclusive

3.5 out of 5
8 Kent Avenue, Montego Bay, Saint James
Free Cancellation
Reserve now, pay when you stay
Get rates
A nightclub, 3 restaurants, and 2 outdoor tennis courts are all featured at this all-inclusive property. Relax with a drink at one of the 4 bars/lounges and enjoy free perks like buffet breakfast and free self parking. Enjoy the outdoor pool and unwind at the beach bar and poolside bar.
Hotel Riu Palace Tropical Bay - All Inclusive

Hotel Riu Palace Tropical Bay - All Inclusive

4 out of 5
Norman Manley Boulevard, Bloody Bay Beach, Negril, Westmoreland
Get rates
A full-service spa, 5 restaurants, and 2 outdoor pools are all featured at this all-inclusive property. Enjoy a day at the beach snorkeling, or relax with sun loungers. Bring the family and enjoy the children's club, children's pool, and playground.
Don't see what you're looking for?
See all available properties in Middlesex
View all properties
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 are vacation packages to Middlesex?
Travelocity offers hotel and flight packages from as low as $1,069. With such great deals, you'll be saying hello to Middlesex in a flash.
Where can I get the best vacation package deals for Middlesex?
There are incredible Middlesex package deals waiting for you with Travelocity. Did you know we partner with 400 airlines and 1,000,000 worldwide properties? Keep that in mind the next time you're ready to check another destination off your travel bucket list.
Why should I book my Middlesex vacation package via Travelocity?
By booking your hotel, flights, activities and car rental altogether, you'll save big bucks as well as precious time. We have a dedicated team of experts available 24/7, and you'll know that you'll always be getting the best deal in town with our Price Match Guarantee. So, what's stopping you? Book your dream getaway today and start packing!
Will I save money on my Middlesex car rental if I bundle it with hotels and flights?
Bundling your hotel, car and flight into a Middlesex vacation package is a surefire way to land the best prices. Plus, having your own rental car gives you total freedom to find your way to all those landmarks you're itching to explore. Located 70 mi from Middlesex, Dunn's River Falls is one place that should be on your to-do list. Buckle up and make a day trip of it.
Which airport is best for Middlesex?
Jetting to Middlesex will see you touching down at Sir Donald Sangster Intl. Airport (MBJ). It's located 18 mi east of the downtown area.

Photos of local treasures

Browse Middlesex vacation photos for more inspiration