Cottages in Castletown
Brimming with history and charm, Castletown, the ancient capital of the Island, makes for a fantastic place to visit on your Isle of Man holiday. Wander the picturesque streets, admire the harbour, and explore Castle Rushen, a majestic medieval castle overlooking the harbour. The Nautical Museum is a fascinating place to visit, where you can see the oldest schooner in the world, Peggy. And after your day of adventures, there are plenty of fantastic restaurants and pubs to stop at for a delicious meal, including The Garrison, Kizuna, and Stanley’s.
Planning an Isle of Man break? We’ll redirect you to our sister company, Island Escapes, but you can hop back anytime to keep exploring UK getaways.
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.
We have 96 self catering cottages in Castletown
Ard Beg
10A delightful mid-terrace cottage in the heart of Castletown
Ard Beg is a delightful self-catering cottage sleeping three people. The master bedroom has a double bed, bedside tables & wardrobe. There is also a spacious single bedroom with be...
Ard Mor
12An inviting end-terrace cottage in the heart of Castletown
Ard Mor is a delightful self-catering cottage sleeping three people. The master bedroom has a double bed, bedside tables & wardrobe. There is also a spacious single bedroom with be...
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.
Ard Lee
11A charming mid-terrace cottage in the heart of Castletown
Ard Lee is a delightful self-catering cottage sleeping three people. The master bedroom has a double bed, bedside tables & wardrobe. There is also a spacious single bedroom with be...
Curlew Cottage
51Curlew cottage is a charming 18th century one bedroom traditional Manx stone cottage in the heart of
Curlew cottage is a charming 18th century one (double) bedroom traditional Manx stone cottage which retains some original features a stone fireplace and open beam ceilings in loung...
British Travel Awards 2025
Best company for UK holiday home rentals
Ivy Cottage
216Charming Castletown cottage with large private garden
Set in the heart of historic Castletown, Ivy Cottage is a beautifully presented holiday home offering spacious accommodation, charming interiors and a surprisingly large private ga...
Dove Cottage
54A delightful stone cottage located in Castletown, minutes from the historic town centre and its pubs
Set within the grounds of a 19th century water mill, this delightful single level self-catering holiday cottage has the perfect mix of private rural setting and easy access to Cast...
Croft End
47Croft End is a newly renovated family friendly home located on a desirable street in Castletown
Croft End is a newly renovated self catering family friendly home located on a desirable street in Castletown, Isle of Man. A spacious open plan ground floor area features a cla...
Mariner's Cottage - Castletown
86Mariner's Cottage is nestled in the historic town centre of Castletown, home to the medieval Castle
A traditional cottage in the heart of Castletown, Isle of Man, a short stroll from the impressive medieval Castle Rushen, picturesque harbour, local bars, shops and restaurants. ...
Ellan Vannin
59An historic home and listed building on the waterfront in the heart of Castletown, the ancient capit
Ellan Vannin is one of a collection of refurbished listed buildings in an historic area of Castletown in the south of the Isle of Man. Adjoining the Bailey Scott designed former Po...
Seafarer's Cottage
109Seafarers Cottage is located on the beachfront in Castletown, the ancient capital of the Isle of Man
Seafarer's Cottage is a traditional cottage with panoramic views of Castletown Bay and beyond. Setting out on foot you could find yourself in the historic town centre within just a...
We are Gold accredited with the Green Tourism Business Scheme.
Green Tourism Business Scheme
As a company, we look across our business and try to make sustainable changes and decisions. From using recycled paper in our printers to putting in measures for using less energy in our offices, we keep an eye on our impact on the environment.
Beyond our offices, we have passed on the same ethics to our holiday cottage owners by setting up our own Green Scheme that they can join. Each property has to tick off a certain number of actions to be included in the scheme, many of which go above and beyond the GTBS requirements.
