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Our writer Michelle found a new favourite family holiday getaway near this beautiful British seaside town, and a holiday home with stunning coastal views and luxury comforts
If you’re looking for a family-friendly getaway with windswept coastal views, a sprinkling of history and plenty of charm, the ‘tied island’ of Portland in Dorset delivers it all. We brought the whole family along, including our 11-month-old cockapoo, who enjoyed himself as much as the kids.
This rugged stretch of Dorset coastline has an untamed beauty about it, with dramatic cliffs tumbling down to hidden coves and curious little footpaths begging to be explored. Our go-to getaway is normally Cornwall, and this change of scenery was a welcome hit with our little ones.
Where to stay in Portland
Our home-from-home was Clifftops at Pennsylvania Castle Estate, a stay that felt luxuriously modern yet still deeply rooted in this ancient landscape.
Perched high above the coast, Clifftops is a collection of sleek lodges offering front-row seats to the sea. We stayed in Clifftops Blue, one of its beautiful two-bedroom apartments, and from the moment we walked in, we felt utterly spoiled. The apartment was immaculate and stylish, with an open-plan living space, a well-equipped kitchen and a state-of-the-art outdoor kitchen/barbecue area if you fancy grilling al fresco. Every detail felt premium yet inviting.
Floor-to-ceiling windows meant we could soak up those sea views at every moment, whether we were curled up on the sofa or enjoying a glass of something chilled on the terrace, which our dog quickly claimed as the best sunbathing spot.
It’s wonderfully dog-friendly; waiting for our pooch was his own welcome pack with dog treats and pet-friendly toiletries. And for us, there was a thoughtful tray with local Portland gin, tonics and snacks.
What to do in Portland
There’s plenty to fill your days in Portland, a mix of natural wonders and historic landmarks. We started at the iconic Portland Bill Lighthouse where we braved the steep spiral staircase to the very top, where we were rewarded with spectacular panoramic views; the friendly staff at Clifftops happily looked after our dog while we did the climb.
We also explored the romantic ruins of Rufus Castle, which overlooks Church Ope Cove, a pretty, pebbly beach where we collected seashells and walked past its famous ‘pirate grave’.
For something a little different, Tout Quarry Sculpture Park was a hit with the kids, who loved hunting for stone carvings hidden among the winding paths. And Portland Castle, a 16th-century coastal fortress, brought the area’s maritime history vividly to life.
Further afield
Weymouth is just a short drive away and perfect if you’re craving classic seaside fun. We headed there for a day of traditional bucket-and-spade beach time and also visited the Sea Life Adventure Park, which was an unexpected hit – we hadn’t realised there was a water play area, so the kids had an impromptu splash about (pack swimwear if you go). The aquarium itself has plenty of interactive zones, and makes for a great family outing if you want to mix up beach days with something indoors.
Of course, no seaside visit is complete without fish and chips, so we finished the day with a takeaway from King Edwards, eating together on a bench looking out to sea – perfection.
How much does it cost?
Clifftops’ luxury lodges start from £546 for three nights. Look out for midweek offers that get you an extra night for free.
