Cottages in Douglas
Douglas, the Island’s capital, is likely to be your first port of call on your Isle of Man holiday. This bustling town offers plenty of places to shop and dine, you can hop on the Isle of Man Steam Railway to visit Castletown or the Manx Electric Railway to explore the Island, and delve into the Island’s history with a visit to the Manx Museum. Stroll along the promenade, admire the beautiful Victorian buildings, and stop off at the popular Noa Bakehouse for a coffee, pastry, and a loaf of bread. Douglas Head is a great place for special views over the bay. And on the edge of the town, you’ll find Summerhill Glen, with its pretty streams and footpaths. In the autumn and winter months, the glen lights up with magical illuminations.
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 35 self catering cottages in Douglas
West View
150West View is a charming annex to a large traditional Mansion house set in it's own grounds just a fe
w minutes walk from the Isle of Man TT Grandstand in Douglas. Whilst located in the island's capital, the secluded nature of the property within the large wooded grounds provide...
Deaks Cottage
53Deaks Cottage is tucked away in a quiet corner of Douglas, just a short walk from the TT Grandstand!
Deaks Cottage is a charming cottage hidden away in the tranquil grounds of a gated Manor House. Its' location is hard to beat, as Douglas town centre and the TT Grandstand are just...
Woodcroft
152Woodcroft is a charming cottage located in wonderfully leafy surroundings right in the heart of Doug
Woodcroft is a charming cottage located in a wonderfully leafy corner of Douglas, Isle of Man. Its' location is hard to beat, as the town centre and the TT Grandstand are just minu...
Ballafletcher Farm Cottage
18Ballafletcher Farm Cottage is a recently renovated cottage situated down a small country lane
NEW FOR 2024 Originally a working farmhouse, Ballafletcher Farm Cottage has been recently renovated to a superb standard. The cottage features two spacious bedrooms, both wit...
Little Haven
84Just off the promenade in Douglas, Little Haven is a cosy cottage refurbished to a high standard.
Little Haven is located in a quiet neighbourhood set just off Summerhill Road, close to the promenade in Douglas, Isle of Man. Close to the Manx Electric Railway, the famous Dou...
Santa Rosa
102Santa Rosa offers captivating views from its elevated position overlooking Douglas bay, Isle of Man.
With 3 bedrooms, Santa Rosa is a self catering holiday cottage providing a perfect base for exploring the Isle of Man. Close to public transport links, the Manx Electric Railway, t...
Loft 11
163Stylish, boutique NYC-style loft in the heart of Douglas.
New for 2025! Tucked away just off Castle Street in the heart of Douglas, Loft 11 is a one-of-a-kind luxury self-catering loft apartment offering a bold and beautifully designed...
Buttermere Drive
29Homestay registered property - only available for bookings during the TT period.
This beautiful property is registered with Homestay IOM Limited and is marketed exclusively through Island Escapes. Buttermere Drive is available for self-catering accommodation ex...
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.
The Lodge
131The Lodge is a large spacious detached house set in its own grounds just a few minutes drive from th
The Lodge is a spacious family holiday home set in its own grounds, sleeping 6 in 3 bedrooms, with an additional double sofa bed in the 4th bedroom made up on request at an additio...
The Hayloft Studio at Rosehill Farm
129One of two apartments in a private location overlooking Douglas
Situated just outside of Douglas in a private location sits The Hayloft Studio, a first floor self catering apartment with panoramic views of the island's capital that stretch out ...
