Deals on vacations and trips to Middlesex

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

Alamanda Cottage at Serenity

3 out of 5
Ironshore
Price was $2,909, price is now $1,094 per person
$1,094
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Ocho Rios Villa Azul at Coolshade XIII

Ocho Rios Villa Azul at Coolshade XIII

3.5 out of 5
Price was $2,414, price is now $1,155 per person
$1,155
per person
Jan 28 - Feb 4
found 10 hours ago
Roundtrip flight included
New York (JFK) to Montego Bay (MBJ)
This vacation home features an outdoor pool and a 24-hour gym. Free self parking, a terrace, and a garden are also offered.
Ocho Rios Treasure Villa at Coolshade XII

Ocho Rios Treasure Villa at Coolshade XII

3.5 out of 5
Price was $2,408, price is now $1,152 per person
$1,152
per person
Jan 28 - Feb 4
found 10 hours ago
Roundtrip flight included
New York (JFK) to Montego Bay (MBJ)
This vacation home features an outdoor pool and a 24-hour gym. Free self parking, a terrace, and a garden are also offered.
Excellence Oyster Bay - Adults Only All Inclusive

Excellence Oyster Bay - Adults Only All Inclusive

5 out of 5
Price was $3,425, price is now $1,686 per person
$1,686
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
This all-inclusive property features a private beach, a full-service spa, and 11 restaurants. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. Enjoy the 2 outdoor pools and perks like free WiFi.
Ocean Eden Bay - Adults Only - All inclusive

Ocean Eden Bay - Adults Only - All inclusive

5 out of 5
Price was $2,737, price is now $1,378 per person
$1,378
per person
Mar 8 - Mar 14
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
This all-inclusive property features a private beach, a full-service spa, and a nightclub. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a lazy river and a bowling alley, and families will appreciate the onsite laundry facilities.

Top Middlesex hotels deals

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
$250 nightly
The price is $275 total per night
$275 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
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.
Pool
Hot Tub
Azul Beach Resort Negril, Gourmet All Inclusive by Karisma

Azul Beach Resort Negril, Gourmet All Inclusive by Karisma

5 out of 5
Norman Manley Blvd Negril Westmoreland
$371 nightly
The price is $431 total per night
$431 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
A full-service spa, 6 restaurants, and 7 outdoor pools are all featured at this all-inclusive property. Dine at the beachfront restaurant and relax with beach umbrellas. There's fun for all ages with a free kid's club and a children's pool, and families will appreciate the picnic area.
Pool
Breakfast included
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.
Pool
Breakfast included
Grand Palladium Jamaica Resort & Spa All Inclusive

Grand Palladium Jamaica Resort & Spa All Inclusive

5 out of 5
The Point Lucea Hanover
$257 nightly
The price is $296 total per night
$296 total
Jan 20 - Jan 21, 2026
Total with taxes and fees
This all-inclusive resort features a private beach, free water park access, and a full-service spa. Relax with sun loungers and beach umbrellas, and enjoy a drink at one of the 3 beachside bars. There's fun for all ages with a free kid's club and mini golf, and families will appreciate the onsite laundry facilities.
On private beach
Pool
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
$370 nightly
The price is $430 total per night
$430 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
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.
Pool
All inclusive
Hotel Riu Negril - All Inclusive

Hotel Riu Negril - All Inclusive

3.5 out of 5
Norman Manley Blvd Negril Westmoreland
Get rates
This all-inclusive property features a private beach, a full-service spa, and a nightclub. There's fun for all ages with a free kid's club and a children's pool, and barbecue grills are available on site. Enjoy a meal in one of the 6 restaurants and perks like free buffet breakfast and free self parking.
On private beach
Pool
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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 $1,094. 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

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