Bargain Madeira Holidays This Winter – Flights and 5 Star Hotel from €299pp!
Explore magical Madeira this winter! Check out these Madeira holidays with flights and 5 star hotels for the ultimate short escape.
Madeira holidays are having their moment! This stunning Portuguese island is the perfect winter escape, offering fewer crowds and excellent value. Whether you’d like to unwind on beautiful beaches, hike the Pico do Arieiro to Pico Ruivo trail, ride the Funchal cable car, try the traditional toboggan, spot whales and dolphins, or taste the world-famous Madeira wine, it’s an ideal choice for a short break.

You can fly direct from either Dublin or Shannon Airport. Ryanair operates direct flights from Dublin to Madeira on Mondays, Wednesdays, and Saturdays, and from Shannon to Madeira on Mondays and Fridays – so there are plenty of options for Madeira holidays in the winter season.
I’ve found return flights from both Dublin Airport and Shannon starting from as little as €48 per person this winter. I’ve outlined two hotel options: one that’s ideal if you enjoy dining out and discovering local restaurants, and another that’s perfect if you’d prefer to stay put and take advantage of all-inclusive food and drinks. Whatever your travel style, there’s a Madeira to suit you.
The dates I have chosen can be changed, simply edit the dates on the links below to suit your requirements.
5 Star Pestana Carlton Maderia, B&B, 3 Nights from €299pp, 4 Nights from €315pp

The Pestana Carlton Madeira sits on a cliffside with breathtaking views over the Bay of Funchal, the harbour, and the surrounding mountains. It’s in a prime location, just a 15 minute walk into the centre of Funchal. Despite being close to the action, the hotel feels like a getaway in itself, with panoramic sea views, direct access to the ocean, and even a cosy pub for relaxed evenings.

This luxury hotel offers four pools including an indoor one, plus a choice of restaurants. Alongside the main buffet, there’s an à la carte grill for something special, and your stay includes breakfast in the price.
Whether you’re soaking up the sun by the pool, enjoying the views, or heading out to explore Funchal’s shops, cafes, and attractions, the Pestana Carlton Madeira makes a convenient base. You can check out the great reviews on TripAdvisor here.
Dublin Departure 4 Nights 13th December
Shannon Departure 3 Nights 21st November
If you wish to go for longer or travel on different dates please edit the links to suit you.
5 Star Pestana Royal Ocean & Spa Resort, All Inclusive, 3 Nights from €350pp, 4 Nights from €448pp

The 5 star Pestana Royal All Inclusive Ocean & Spa Resort enjoys a clifftop setting just a short stroll from Formosa Beach and only a 10 minute taxi from Funchal’s city centre. This hotel has everything you need for a relaxing getaway, from a large pool with a swim-up bar to a choice of restaurants, including Italian, Madeiran and a buffet.
Guests can also unwind in the spa with treatments ranging from massages to facials, or sip cocktails in one of the two bars. With Madeira’s biggest beach nearby and all inclusive food and drinks included, Pestana Royal makes the perfect base for a stress-free holiday.
Dublin Departure 3 Nights 10th December
Dublin Departure 4 Nights 22nd November
If you wish to go for longer or travel on different dates please edit the links to suit you.
Things to do in Madeira

Depending on the type of holiday you are looking for, you may want to see some of the most popular attractions in Madeira. If you’re a football fan, don’t miss the CR7 Museum dedicated to Cristiano Ronaldo, if you like hiking then I’m sure you will love Madeira’s many amazing trails, or choose a more relaxing activity such as wine tasting or a sunset cruise.
If these Madeira holidays don’t suit we have many other options for winter short breaks and sun holidays below
Read: 10 Great Value Winter Breaks
Read: Escape The Cold This Winter: 12 Cheap Winter Sun Holidays
For more Madeira holidays with deposit options and payment plans available search below
I hope these bargain Madeira holidays will have you jetting off to explore the island soon. Prices and descriptions are correct at the time of issue but are subject to change. Please note that some of the links in this girly getaways post are affiliate links, where I will receive a small commission if a booking is made, but at no additional cost to you.








