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 29 available cottages and secure your September retreat today.
We have 29 Dorset cottages available in September
7 nights from £508
Phoebes House
29242 bedroom, rural self catering cottage near Beaminster, Dorset.
A stunning west Dorset location, amazing rural views and a truly luxurious property, Phoebes House is a hidden gem just a short drive inland from the famous Jurassic Coast. This de...
7 nights from £508
7 nights from £483
Meadowbank
26443 bedroom holiday cottage near Bridport, Dorset.
This sunny south-facing cottage enjoys a quiet rural position on the edge of the beautiful village of Netherbury, a short drive from the beaches and cliffs of the World Heritage Ju...
7 nights from £483
7 nights from £502
The Parlour
26622 bedroom, rural cottage near the beach near Bridport, Dorset.
The Parlour is an excellent choice for a family, with French windows opening out onto an enclosed gravelled patio, comfortable accommodation for five guests – one of the three sing...
7 nights from £502
7 nights from £567
Hatts Barn
20932 bedroom, rural holiday cottage near Shaftesbury, Dorset.
Semi-detached Hatts Barn is a contemporary, reversed level barn conversion on a wide south-facing terrace. The large en suite master bedroom and a twin bedded family room (the beds...
7 nights from £567
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20% off
29 Mar 2019 - 5 Apr 2019
£536.36 £429.09
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 £635
Old Down Cottage
19343 bedroom, dog friendly cottage near Wimborne Minster, Dorset.
This is an excellent base for exploring rural and coastal Dorset. Cranborne Chase (an Area of Outstanding Natural Beauty) is on the doorstep, and the beaches of the Jurassic Coast ...
7 nights from £635
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20% off
5 Apr 2019 - 12 Apr 2019
£730.28 £584.22
7 nights from £649
Barn Owls Cottage
30153 bedroom, dog friendly self catering cottage near Bridport, Dorset.
Barn Owls Cottage, a semi-detached cottage converted from an 18th Century stone barn, has retained much of its original character with inset fossils and huge oak beams. The kitchen...
7 nights from £649
7 nights from £652
Sturthill Stable
28293 bedroom, dog friendly self catering cottage near Bridport, Dorset.
This beautiful barn conversion at the heart of a working dairy farm is just inland from Dorset's spectacular Jurassic Coast and its beaches. The rural setting will please all the f...
7 nights from £652
7 nights from £701
Tolpuddle Cottage
37523 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.
This very pretty thatched cottage is in the tranquil historic village of Tolpuddle, surrounded by beautiful countryside and just 15 miles from the World Heritage Jurassic Coast. Wi...
7 nights from £701
7 nights from £704
Dairy Cottage
31923 bedroom, dog friendly holiday cottage near Lyme Regis, Dorset.
Imagine spending a week in a fabulous former dairyman’s cottage with all mod-cons! This very stylishly furnished, yet quirky, semi-detached cottage is in the village of Morcombelak...
7 nights from £704
7 nights from £720
2 Penny’s Cottages
25313 bedroom holiday cottage in Corfe Castle, Dorset.
You will be completely spoilt for choice in this stunning part of Dorset – along the Jurassic Coast and within very easy reach are Lulworth Cove and Durdle Door with their famous c...
7 nights from £720
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.