Cottages for large groups in South of the Island
These spacious UK getaways are perfect for reunions with friends or family get-togethers, with pools, balconies and games rooms galore. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 15 self catering cottages for a group in South of the Island
Bay View House
214Large town house in Port Erin with view of Bradda head
Bay View is a beautifully renovated six-bedroom townhouse in the heart of Port Erin, offering stylish and spacious accommodation for large families, groups of friends, and multi-ge...
Highfield
198Homestay registered property - only available for bookings during TT & MGP periods.
This beautiful property is registered with Homestay IOM Limited and is marketed exclusively through Island Escapes. Highfield is available for self-catering accommodation exclusive...
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!
Seaspray
180Luxury beachfront retreat with panoramic sea views.
Seaspray is a luxurious 4-Star Gold self-catering retreat set right on the beach at Port Erin. Beautifully renovated throughout, this contemporary coastal haven combines comfort an...
The Studio
140The Studio is a seaside escape based in the quiet hamlet of Derbyhaven, just outside Castletown in t
The Studio is a recently refurbished self-catering tourist accommodation based on the seaside in Derbyhaven, a quiet hamlet near Castletown in the south of the Isle of Man. Comf...
-
10% off
15 Aug 2026 - 28 Aug 2026
British Travel Awards 2025
Best company for UK holiday home rentals
Awelon
14A premium escape located on the sought after Port Erin beach
Awelon is a premium self-catering holiday home located on the beachfront of Port Erin, with fantastic views of the beach, Port Erin Bay and Bradda Head, featuring Milner's Tower. ...
The Arches Holiday Haven
120A beautiful large 5 star gold award property built recently to exacting specifications, situated at
Situated at the end of a quiet close, The Arches Holiday Haven self catering house is ideally placed for a family holiday, or several couples looking for somewhere for a convivial ...
Eary Cushlin
56In partnership with Manx National Heritage, we are pleased to present Eary Cushlin; a large house on
Hidden on the rugged western coastline just beneath Cronk ny Arrey Laa, sits the former home of eccentric recluse Colby Cubbon, who purchased the property hoping to escape the Germ...
Thie Fuinnee
145Thie Fuinnee is a spacious self-catering holiday home situated in the peaceful harbour-side village
Thie Fuinnee is a spacious self catering holiday home situated in the peaceful harbour-side village of Port St Mary on the Isle of Man. The property itself is located just round th...
Bradda Place
25Nestled in a peaceful location, just 100 yards from the promenade
Bradda Place is the perfect base for a holiday on the Isle of Man. With 4 guest bedrooms this versatile property caters for all from large family groups to friends and couples wish...
Salt Wood
101An incredible waterfront property on the harbourside of Port St Mary, Isle of Man
There are few properties on the Isle of Man like Salt Wood. From the moment you step inside you'll feel the care and attention gone into making this a truly magical home by the ...
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 more the merrier, when it comes to a South of the Island holiday. So get everyone together, friends, family even the pets and spend some quality time reacquainting with each other. Holidays are when the best memories are made so make sure none of your loved ones is missed out of the fun with one of our South of the Island cottages for a large group.
Why not make the most of your large holiday cottage and book a private chef to host you, and your group. Whether it's a family gathering, a friends' weekend or you're celebrating something special, you can now add an unforgettable dining experience to your stay - without lifting a finger.
