Two night breaks in South of the Island
A weekend away or two night short break in South of the Island is so simple. No major preparations or need to pack up your life, just the perfect excuse to get away from it all for your favourite holiday cottage and slip under the radar of everyday life. With hand picked cottages across the UK, there are endless places to escape to for a two night break with Classic Cottages. Take a look and see...
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 88 holiday cottages available in South of the Island for a two night break
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...
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...
Calf View
206Tranquil Cregneash cottage overlooking the Calf of Man
Perched above the timeless village of Cregneash, Calf View is a serene cottage with views framed by sweeping Manx vistas stretching towards shimmering seas and the wild beauty of t...
Surby Mount
204A delightful rural setting near Port Erin, ideal for families.
Surby Mount is a beautifully appointed detached countryside retreat tucked away in peaceful Surby, just a few minutes from the coastal village of Port Erin. Surrounded by rolling f...
British Travel Awards 2025
Best company for UK holiday home rentals
Spring Cottage
203A cosy hideaway overlooking Port Erin and the south
Welcome to Spring Cottage, a beautifully refurbished self-catering holiday cottage set high above Port Erin and Port St Mary on Ballakillowey in the scenic south of the Isle of Man...
Abbey at Trail Lodge
174Stylish studio apartment located in an idyllic national glen.
Abbey at Trail Lodge is a modern self-catering studio apartment set within the beautifully restored Silverdale Corn Mill, surrounded by the peaceful Silverdale Glen near Ballasalla...
Silverburn at Trail Lodge
170Stylish studio apartment located in an idyllic national glen.
Silverburn at Trail Lodge is a modern self-catering studio apartment set within the beautifully restored Silverdale Corn Mill, surrounded by the peaceful Silverdale Glen near Balla...
Duxbury Lodge
201Dog-friendly elegant countryside lodge for two
Duxbury Lodge is a contemporary barn conversion set alongside Duxbury Cottage, offering a stylish rural retreat for two in the south of the island. Thoughtfully designed and beauti...
Sea Salt
199Refined boutique stay near Castletown’s harbour & history
Sea Salt is a beautifully refurbished hideaway on historic Queen Street, offering an indulgent blend of contemporary luxury and homely warmth in the heart of Castletown. Thoughtful...
Seaview
181An elegant coastal escape with uninterrupted sea views
Seaview is a beautiful coastal cottage set directly on the promenade at Port Erin beach, offering tremendous panoramic views of the sea from almost every room. Perfectly positioned...
British Travel Awards 2025
Best company for UK holiday home rentals
