Holiday Cottages for September
September is around the corner and a holiday in a self-catering cottage is beckoning. With the last of the summer sunshine, warm sea temperatures from months of hot weather and the crowds starting to dwindle, September is a fantastic time to enjoy a holiday in a home-from-home. Solo retreat, family holiday or gathering with friends, our cottages provide an idyllic base from which to enjoy a perfect getaway. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 1384 holiday cottages available in September
7 nights from £1275
Dormy House
60843 bedroom, dog friendly holiday cottage near the beach in Hunstanton.
Dormy House is single-storey beach house, nestled in an idyllic spot, just moments away from the stunning beaches of this much-loved village, along the north west Norfolk coastline...
7 nights from £1275
7 nights from £582
The Bothy
61251 bedroom, dog friendly self catering cottage near Skipton.
If you are craving a cosy getaway for two or a quiet friend's weekend, The Bothy is a great choice. It is a traditional, restored stone cottage sitting right in the heart of the de...
7 nights from £582
From £900 per night
The Retreat
61215 bedroom, dog friendly self catering cottage near Crickhowell.
The spellbinding beauty of the Bannau Brycheiniog (Brecon Beacons) are calling you for your next celebration or larger get-together. Escape to the hills at the exquisite The Retrea...
From £900 per night
7 nights from £1120 *
12 Castle Street
61304 bedroom, dog friendly self catering cottage near Ruthin.
Step into a world of timeless elegance and sheer comfort in 12 Castle Street, where classic charm meets modern luxury and pure relaxation. Escape to this superbly renovated Victori...
7 nights from £1120 *
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £585
Caban Tarren
6115Cabin in Wales with wood-burner and outdoor kitchen.
Full of charm and soul, this cabin nestled in the heart of the Welsh countryside offers the ultimate escape, surrounded only by rolling hills and mountain views – dreamy. Built...
7 nights from £585
7 nights from £1020
Harecroft
60974 bedroom, dog friendly cottage near the beach in Old Hunstanton.
Harecroft is a single-storey holiday home, set within generous gardens and sleeping up to six guests across four bedrooms. Nestled within a quiet, leafy lane in one of Norfolk's mo...
7 nights from £1020
Rycroft House
205Where light, space, and coastal calm meet in style
Tucked away at the top of a quiet cul-de-sac in the heart of Laxey, Rycroft House is a striking contemporary retreat where thoughtful architecture and coastal calm come together ef...
7 nights from £855
La Cabana
61023 bedroom cottage with sea views in Portscatho, South Cornwall.
Portscatho is a rather charming coastal village on the Roseland peninsula with gorgeous views over Gerrans Bay, easy access to the wonderful coast path and a vibrant centre with a ...
7 nights from £855
7 nights from £1599 *
Oak Tree House
61124 bedroom, dog friendly holiday cottage near Dorchester, Dorset.
Oak Tree House is a particularly special property for gathering friends and family (plus the four-legged variety) together. Set in stunning grounds in the little village of Frampto...
7 nights from £1599 *
Surby Mount
204A delightful rural setting near Port Erin, ideal for families.
Surby Mount is a beautifully appointed countryside retreat tucked away in the peaceful Surby, just a few minutes from the coastal village of Port Erin. Surrounded by rolling farmla...
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 beaches are inviting, the sea's had all summer to warm up and the schools have gone back, so make the most of quieter scenes still drenched in warm sunlight and give yourselves something to smile about. With our range of self-catering cottages, guests of all ages will settle straight in. Whether you are looking for a cottage nestled in the heart of lush countryside, a seaside sanctuary affording spectacular sea views or a town hub offering access to lots of local amenities, we will help you pave the way to your dream holiday this September. Offering a wide range of facilities, from enclosed gardens with barbecues, to homes with private swimming pools to properties with games rooms for kids, let your imagination run wild thinking about all the possibilities for your holiday in a Classic cottage.
Holiday Cottages for September
At Classic Cottages we pride ourselves on marketing only the finest quality self-catering accommodation around. Combining the highest level of customer service with luxury cottages, we want your whole holiday to be the best it can be. Browse our portfolio for September and find your favourite now.
