Cottages for 5 people in South England
For a family escapes or with groups of friends in South England we have hand-picked 82 holiday cottages that sleeps five or more!
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 82 cottages that sleep 5 in South England
7 nights from £717 booking fees included
7 Sandpipers
35683 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
Perfectly situated in the heart of the popular sailing village of Seaview on the eastern side of the Isle of Wight, 7 Sandpipers is a well-equipped town house set across three floo...
7 nights from £717
7 nights from £924 booking fees included
10 Shanklin Manor
35113 bedroom, rural self catering apartment near the beach in Shanklin, Isle of Wight.
This superb two-storey, first floor apartment dating back to 1863 is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interior and the use of a la...
7 nights from £924
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £943 booking fees included
Limpets
46223 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
This gorgeous home, just a stone's throw from the seafront, has sea views from the sitting-room and the luxury of your very own private garden, giving it all the ingredients for a ...
7 nights from £943
From £239 per night + £53 booking fees
Stargazers' Retreat
5125Luxury Yurt for 5 with sea views and outdoor bathtubs near Ventnor, Isle of Wight.
Welcome to Stargazers' Retreat, a heavenly glamping yurt nestled in rural splendour on the southerly tip of the Isle of Wight with blissful views of Reeth Bay and beyond. Situated ...
From £239 per night
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £676 booking fees included
25 Palmerston Road
35383 bedroom self catering cottage near the beach in Shanklin.
Welcome to 25 Palmerston Road, a delightful holiday home perfectly situated in the charming town of Shanklin and just a short stroll away from the golden sandy beach and a good sel...
7 nights from £676
7 nights from £686 booking fees included
Lucaster
43073 bedroom, dog friendly holiday cottage near the beach in Fishbourne, Isle of Wight
This gorgeous, cosy, former coastguard's cottage sits in a peaceful setting in Fishbourne and is just a few yards from the sea and the welcoming local pub. Lucaster is perfectly pl...
7 nights from £686
7 nights from £693 booking fees included
East Gull Sands
35953 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Seaview is a much sought-after and very charming village on the Isle of Wight and East Gull Sands sits in a magical position overlooking the beach, just a short stroll away from th...
7 nights from £693
7 nights from £695 booking fees included
Lawn End
36173 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Tucked away in a quiet corner of the delightful village of Seaview, Lawn End is a cosy island retreat, tastefully furnished to offer contemporary living for families or a group of ...
7 nights from £695
7 nights from £712 booking fees included
Bentinck
57243 bedroom cottage near the beach in Ventnor.
With everything you could wish for on your doorstep for a blissful Isle of Wight holiday experience with family or friends, Bentinck is a great base to explore all that this Island...
7 nights from £712
7 nights from £730 booking fees included
Pandora Lodge
36423 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
Perfectly situated in the heart of the delightful village of Seaview on the Isle of Wight, Pandora Lodge is a lovely, spacious ground floor apartment forming part of a larger prope...
7 nights from £730
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.
