Self-Catering Cottages in Dorset for September
See Dorset bathed in the late summer sunshine this September and enjoy the opportunity to unwind. September enjoys a slower pace with many of Dorset's summer crowds tapering off and the county truly relaxed under blue skies. Whether you are looking for a solo adventure, romantic retreat or catch up with friends in luxury accommodation, enjoy a dream holiday in a Classic cottage. Read more
From country to coast, make the most of Dorset's natural gems and patchwork of towns and villages this September. With life slowing down a gear as children go back to school and summer visitors head home, September is a wonderful time for a Dorset getaway. Walk, talk and explore by day and then when you are ready to turn in, open the door to your dream home-from-home. At Classic Cottages we know a thing or two about what makes holidays great and will always go the extra mile to make sure your whole experience is the best it can be. Across Dorset, our cottages are wide in variety and consistent in quality. Many are dog-friendly too, which is great news for your four-legged friend. Take a look at our 42 available cottages and secure your September retreat today.
Our exclusive ferry discounts will make your island trip with Classic plain sailing.
We have 42 Dorset cottages available in September
7 nights from £598
Pippins
53603 bedroom, dog friendly character cottage near Beaminster, Somerset.
Pippins is a picture postcard country cottage nestled in the charming Somerset village of North Perrott - not far from the Dorset border. This cosy home can cater for all of the fa...
7 nights from £598
7 nights from £1110
Seymour Barn
53142 bedroom, dog friendly barn conversion in Bridport, Dorset.
With the bustling market town of Bridport within striking distance, this beautiful barn conversion is the perfect home-away-from-home. A delightful spot to explore all the beauty a...
7 nights from £1110
7 nights from £1287
Acorns
48283 bedroom cottage in Corfe Castle, Dorset.
Set on a private, secluded plot, Acorns is a wonderful family holiday home. Recently renovated to a very high standard, this detached house in the historic village of Corfe Castle ...
7 nights from £1287
7 nights from £772
Bay Tree Cottage
48353 bedroom, dog friendly cottage near Bridport, Dorset.
Situated in a sleepy west Dorset village, just a short drive from the spectacular Jurassic Coast, you will find this pretty terraced cottage. Bay Tree Cottage offers all the deligh...
7 nights from £772
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.
7 nights from £778
Rectory Cottage
47952 bedroom cottage near Bridport, Dorset
Hidden away in the grounds of a Grade II Listed former rectory, this picture-perfect cottage is a delightful Dorset escape. From the moment you pull into the driveway you will love...
7 nights from £778
7 nights from £740
Fox Cottage
47121 bedroom stylish cottage in Beaminster, Dorset.
Tucked away in an oh-so-pretty part of historic Beaminster, Fox Cottage is a gorgeous retreat for two. As soon as you arrive at this picture-perfect terraced cottage, you will want...
7 nights from £740
From £100 per night
Toby's Hut
4723Luxury dog friendly shepherds hut with a hot tub near Lyme Regis, Dorset.
Located in the west Dorset Area of Outstanding Natural Beauty and just a 15 minute drive from fabulous Lyme Regis, Toby's Hut is a bespoke Shepherd's Hut, sitting in a perfect spot...
From £100 per night
From £86 per night
La Cabine Francaise
47261 bedroom, dog friendly Shepherds Hut near Dorchester, Dorset.
Welcome to La Cabine Francaise, a glorious expanse of glamping bliss with a French twist. Set in the stunning Dorset countryside, this exclusive spot for two provides the perfect r...
From £86 per night
7 nights from £537
Swallows' Rest
46441 bedroom, dog friendly cottage near Beaminster, Dorset.
The sleepy west Dorset countryside awaits you at this cute bolthole for two (plus your four-legged friends). Tucked away at the end of the owners' garden, this converted barn is hi...
7 nights from £537
7 nights from £1185
The Old Mill
45032 bedroom, unique, dog friendly converted mill near Dorchester, Dorset.
If you are looking for a beautifully unique and special property for a perfect Dorset holiday, then look no further than The Old Mill. Formerly a working mill, this gorgeous proper...
7 nights from £1185
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!
