Holiday cottages with 5 bedrooms in South England
Browse the 11 large holiday cottages with 5 bedrooms in South England that we’ve selected for our portfolio. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 11 self catering cottages with 5 bedrooms in South England
Kingston Barns
7 nights from £2663.93 booking fees included
7 nights from £2043 booking fees included
Pickeridge Barn
52166 bedroom, dog friendly self catering home near Haywards Heath.
This beautifully converted eco-friendly barn is rather unique, the perfect holiday home for those looking for a multi-family getaway in the heart of the Sussex countryside. Situat...
7 nights from £2043
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7 nights from £2790 booking fees included
St Andrews
46416 bedroom, dog friendly holiday home with hot tub near the beach in Yarmouth, Isle of Wight.
Looking for a truly unique getaway? This beautiful, converted church offers an unforgettable Isle of Wight escape, blending historic charm with modern convenience. Perched in an el...
7 nights from £2790
Kingston Barns
7 nights from £2013.00 booking fees included
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £2195 booking fees included
Redworth
45415 bedroom self catering home near the beach in Bembridge, Isle of Wight.
This impressive five bedroom house is located on Ducie Avenue, a charming unmade road leading to the beach, in the village of Bembridge. Located within a few minutes walk of the lo...
7 nights from £2195
7 nights from £2363 booking fees included
Cara Cottage
48465 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Welcome to Cara Cottage, a stunning detached property located in the heart of Bembridge village. This eye-catching holiday home with soft pink 'Spanish inspired' exterior is beauti...
7 nights from £2363
7 nights from £2102 booking fees included
Ridge House
39915 bedroom, dog friendly holiday home close to the beach, near Lymington.
On the edge of the New Forest this fabulous home is the perfect summer escape. Set in the stylish seaside village of Milford on Sea and within a 10 minute walk of the beach, Ridge ...
7 nights from £2102
7 nights from £1220 booking fees included
Creekside
35885 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.
Aptly named and perfectly positioned on the banks of pretty Wootton Creek on the north coast of the Isle of Wight, Creekside is a gorgeous waterfront holiday home with delightful v...
7 nights from £1220
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15% off
17 Jul 2026 - 24 Jul 2026
From £2170.00 £1853.95 booking fees included
7 nights from £1561 * booking fees included
Pepita
57195 bedroom, dog friendly holiday cottage with sea views in Seaview.
With breathtaking sea views and the beach only a few steps from the front door, two former coastguard cottages and the adjoining boathouse have been transformed into an island gem,...
7 nights from £1561 *
7 nights from £847 * booking fees included
6 Seafield Terrace
35625 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
6 Seafield Terrace is a charming, spacious terraced cottage set in the pretty village of Seaview. It would ideally suit a large family, several couples or a group of friends travel...
7 nights from £847 *
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.
A holiday cottage in South England with five bedrooms makes the perfect base for a family reunion or a group of friends to get away together. With a range of bedroom types available, there are plenty of options to choose from: doubles, singles, twins and the occasional bunk. But never a sofa bed or put-me-up – we only accommodate as many people as there are proper beds. Use the filters on the left to help find the right one for you.
