Clifftops - Pennsylvania Castle Estate
© Jonathan Gooding

My unforgettable clifftop getaway at the Dorset coast's most underrated destination

A stay at Clifftops on the Penn Castle Estate put the beautiful Isle of Portland firmly on the map for me

Updated: October 4, 2024

Cornwall and Devon have long held the top spots in British holidaymakers' hearts, but the Isle of Portland deserves to be on everyone's radar.

A stone's throw away from Weymouth, the southernmost point of Dorset is a hidden gem with luxury accommodation rivalling its (often eye-wateringly) expensive rivals.

© Jim Stephenson

Clifftops luxury lodges on the Penn Castle Estate put the Isle of Portland firmly on the map for me

The underrated summer staycation spot on England's south coast stands at just six kilometres long and 2.7 km wide – making it very drivable and the perfect place for a whistlestop visit.

The spectacular Clifftops luxury lodges provided the perfect backdrop to my 48-hour minibreak, which included an early morning sauna with locals, trekking along the iconic Chesil beach, and English sparkling tasting at Langham Wine Estate.

 Rooms with a view

© Laura Dean

The southernmost point of Dorset is a hidden gem with luxury accommodation rivalling its more expensive neighbouring counties

Newly opened in 2020, Clifftops is unlike any other self-catered accommodation I have stayed in. Forget your standard seaside Airbnbs: these five uniquely designed lodges are carved out of the Portland stone cliffs that sit on the edge of Penn Castle Estate wedding venue.

Secluded yet open to the elements, the beautiful Blue lodge brought the rugged landscape inside thanks to floor-to-ceiling windows in the living room, complete with a wildlife-watching nook featuring binoculars.

© Clifftops - Pennsylvania Castle Estate

The spectacular Clifftops luxury lodges provided the perfect backdrop to my 48-hour minibreak

The lodge, which is pet friendly, boasts two spacious bedrooms and two bathrooms, making it ideal for a family trip or two couples - and the master, with its heavenly mattress and sea view, was the cherry on top.

Immaculately designed with sleek, Scandi walnut cabinetry and Le Creuset kitchenware, the kitchen offered everything we needed to prepare meals. Meanwhile, a Bose portable sound system and a Samsung smart TV made our stay comfortable, providing the soundtrack for watching the sun setting over the UNESCO World Heritage Jurassic coast.

© Clifftops - Pennsylvania Castle Estate

The kitchen was immaculately designed with sleek, Scandi walnut cabinetry and Le Creuset kitchenware

One thing I particularly loved about Clifftops was the privacy of the place – while the reception team was on hand for emergencies and the Hayloft café was adjacent to the lodges, we didn't see a soul and found the lock-box check-in process seamless.

We also didn’t hear a peep from our neighbours despite their close proximity. The five lodges, each with a unique design focus inspired by the rugged natural landscape, can be rented individually or booked together to accommodate up to 20 guests. 

© Clifftops - Pennsylvania Castle Estate

The beautiful Blue lodge brought the rugged landscape inside thanks to floor-to-ceiling windows

The complimentary local gin got us into the party spirit as we toasted to a wonderful weekend from the spectacular glass-walled balcony with unparalleled views over the English Channel.

Getting back to nature

Tearing ourselves away from the luxury lifestyle, we woke at dawn for a visit to The Island Sauna. Newly opened in June, the tiny wooden cabin in a car park by the water’s edge has already become a mainstay with local residents.  

© The Sauna

The Island Sauna was worth the early morning alarm

Open every morning from 7.30 am and evenings from 5 pm, the sauna is a hugely popular pre-work activity. I crammed in with regular sauna-goers for an authentic experience, complete with a woollen hat to help regulate my body temperature.

Curating the perfect sauna experience is a fine art, and business owner Emma is now passionate about sharing her findings with others, crediting saunas for changing her perspective on life. 

© We Are Weymouth/Andy Cooke

I was left feeling euphoric from the early morning experience

While saunas are beneficial for everything from muscular pain to improving sleep and heart health, the mental benefits shouldn't be overlooked. My usually anxious mind was stilled and I was left feeling euphoric from the early morning experience after cooling off in the freezing water.

The nature high continued with a long walk on Chesil Beach, one of England’s only World Heritage sights, retracing the same steps from the iconic Saorise Ronan film based on the book of the same name.

© Clifftops - Pennsylvania Castle Estate

The secluded Church Ope Cove is accessible from Clifftops via a steep downhill footpath

After basking in the sun (walking on the pebbled beach is hard work), a visit to Church Ope Cove was in order. The secluded beach minutes from Clifftops is accessible via a steep downhill footpath. Lesser populated, the pretty cove is overlooked by dozens of local residents’ beach huts and a haven for wildlife.

Much to my amazement, I saw a seal basking in the sunshine, unbothered by tourists as it sunned itself in the late afternoon rays.

Vineyard visit

© Lara Jane Thorpe

Langham Wine Estate made for the perfect stop-off en route back to London

No weekend away would be complete without a liberal amount of wine consumed. Langham Wine Estate on Crawthorne Farm, northeast of Dorchester, made for the perfect stop-off en route back to London, breaking up the 3.5-hour drive (no drinking and driving occurred, Scout’s honour)

Head Winemaker Tommy Grimshaw imparted his wealth of knowledge as we traipsed around the vineyard, revealing how the 34-hectare operation in rural Dorset was born out of owner Justin Langham’s family passion and has grown from strength to strength.

© Lara Jane Thorpe

The 34-hectare operation in rural Dorset was the perfect pitstop en route home

Citing their biggest competition as France’s champagne houses rather than fellow British winemakers, it’s not hard to see why the award-winning English sparkling producers are at the top of their game.

The lush, green terroir harvests Chardonnay, Pinot Noir and Meunier grapes, and the newly renovated bar complete with outdoor seating area was ideal for putting the goods to the test. At the heart of their wine business is passion; a small, dedicated team who are truly invested in making the best quality sparkling – and after the wine tasting, I was converted.

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On the long drive back to London, I was left reflecting on how much the Isle of Portland has to offer. My staycation Clifftops was short and sweet, but it certainly made a big impression.

A stay at Clifftops' Blue lodge on the Isle of Portland starts at £663 for 3 nights. Find out more at thepennestate.co.uk/the-estate/clifftops.

48 hours on the Isle of Portland

DO

Watersports! The island is ideal for all manner of aquatic activities including kite surfing, windsurfing, paddle boarding, SCUBA diving and, of course, sailing.

VISIT

Portland Bill is a must-visit. Standing tall at 135 ft, the unique working lighthouse hosts daily tours – but be warned, they're not suitable for anyone with a fear of heights. Grab a bite for lunch at the bustling café to re-energise before conquering the rocky waterfront walk.

© We Are Weymouth/Andy Cooke

Portland Bill is a must-visit

BATHE

Church Ope Cove is a secluded summer haven. The pebbled beach is home to amazing wildlife.

DINE

Billy Winter's is hugely popular with locals: fairly priced and with a wide-ranging menu, it's the ideal spot for a post-swim bite to eat. The fish and chips hit the spot.

SNACK

The Hayloft Café is a sweet spot for mid-afternoon cake and coffee. Grab a pastry and a brew and soak up the afternoon sunshine on their outdoor terrace.

TOUR

Langham Wine Estate hosts highly informative tours – culminating in a tasting of their top English sparkling wines. A 1.5-hour Winemaker’s Tour costs £37.50 per person.

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