We have 96 self catering cottages in Castletown
The Pines
137The Pines boasts a spectacular elevated position overlooking the coastal village of Port Erin, with
Tucked into the Bradda hillside overlooking Port Erin in the south of the Isle of Man, The Pines is sufficiently removed from the village to provide a private, idyllic feel yet clo...
Spaldrick View Cottage
115A historic former fisherman's cottage with breathtaking views over Port Erin bay
Perched above Spaldrick Beach, Spaldrick View Cottage is a charming former fisherman's cottage with panoramic views of the Calf of Man and Bradda Head. A hidden gem on the Isle of ...
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
Sound of the Sea
114A spacious apartment with stunning elevated panoramic views across Port Erin bay and out to sea.
Sound of the sea is a newly refurbished 3 bedroom apartment in a lovely location sitting overlooking Port Erin bay, in the south west of the Isle of Man. Located on the top floo...
Shee Dy Vea
112Shee Dy Vea is a beautiful home in a peaceful area overlooking Port Erin bay.
Shee Dy Vea is a charming, family-run self-catering holiday home set in a peaceful spot overlooking the beautiful bay of Port Erin in the south of the Isle of Man. With its relaxed...
Thie Aash
155A modern countryside retreat with a wood-fired hot tub.
Nestled just off the Ballamodha Straight in the heart of the Isle of Man, Thie Aash offers a sleek and stylish countryside retreat. Surrounded by open landscapes and rolling hills,...
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15% off
28 Aug 2026 - 31 Aug 2026
Thie Ny Shee
156A modern countryside retreat with a wood-fired hot tub.
Tucked away just off the Ballamodha Straight, Thie Ny Shee offers a peaceful escape in the heart of the Isle of Man's countryside. This beautifully presented single-storey property...
The Milking Parlour (Port Erin)
133The Milking Parlour is a recently refurbished farm building in a rural setting overlooking Port Erin
, Isle of Man. The property consists of a double bedroom, twin bedroom and shower room on the ground floor with stairs leading up to a spacious open plan lounge, kitchen and din...
The Views Cottage
143The Views Cottage is a stone farmhouse overlooking Port Erin bay, with panoramic views stretching as
The Views Cottage is a self-catering stone built farmhouse. Situated on Bradda hill and overlooking Port Erin bay, there are panoramic views from Langness to the Calf of Man. Th...
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!
Corner Cottage at Corlea Farm
42A stunning cottage set in private grounds in the south of the Isle of Man.
Corner Cottage is a stunning self catering holiday cottage finished to a superior standard in private grounds. This cottage boasts stunning coastal views to the front and access...
The Old Stables at Corlea Farm
136The Old Stables is a stylish and well-equipped self-catering cottage nestled at the base of South
The Old Stables is a traditional stone build, renovated to provide modern comforts while retaining its rustic charm. This cottage is located in the tranquil countryside of the I...
