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 79 self catering cottages in Castletown
Ard Beg
10Ard Beg is a delightful mid-terrace cottage situated 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 Lee
11Ard Lee is a charming mid-terrace cottage situated 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...
Ard Mor
12Ard Mor is an inviting end-terrace cottage situated 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...
Curlew Cottage
51Curlew cottage is a charming 18th century one bedroom traditional Manx stone cottage in Castletown
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...
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
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...
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.
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...
Gee's Cottage
65Gee's Cottage is located on the beachfront in Castletown, the ancient capital of the Isle of Man.
Gee's Cottage is a self-catering holiday cottage with panoramic views of Castletown Bay, located just across the harbour from the centre of Castletown and its' imposing Castle Rush...
