September Holidays in Somerset
Squeeze out the last drops of summer and head to Somerset for an unforgettable holiday. Enjoy the September sunshine illuminating Somerset's beautiful landscapes and spend your days making the most of the late summer vibes. Then, when you are ready to turn in, return to your own slice of paradise in a luxury self-catering retreat. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.Select from 32 Somerset cottages available for September
7 nights from £1098 * booking fees included
The Cygnet - Lodge 11
60442 bedroom self catering cottage near Lyme Regis, Somerset.
Situated on the Cricket St Thomas estate and close to the borders of Somerset, Dorset and Devon, is The Cygnet - Lodge 11, a luxury Scandinavian style lodge. It is part of the sele...
7 nights from £1098 *
7 nights from £860 * booking fees included
The Old Dairy
60822 bedroom, dog friendly self catering cottage near Taunton, Somerset.
The Old Dairy is a warm and cosy conversion set in the picturesque rolling hills of north Somerset. It offers spacious accommodation for up to four guests and will really strike a ...
7 nights from £860 *
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20% off
31 Jul 2026 - 7 Aug 2026
From £919.80 £748.44 booking fees included
Choose from our exclusive collection at the best prices with real time availability.
Exclusive cottage collections
Our calendars show live availability, so if your pick of dates are available, you can reserve them safe in the knowledge that they won’t get sold anywhere else.
It can be unpredictable using aggregator websites that collect up information from across multiple websites. Our website stands alone, so you know what to expect and what you will get, for the best price. You won’t find this collection of cottages anywhere else, so pick your perfect place to stay from our exclusive portfolio.
7 nights from £771 booking fees included
The Byre
60661 bedroom self catering cottage near Taunton, Somerset.
**The Byre can accommodate flexible check in days – please contact us to request.** Located in the picturesque Blackdown Hills near the Somerset and Devon border you will find T...
7 nights from £771
7 nights from £837 booking fees included
The Stables
60651 bedroom self catering cottage near Taunton, Somerset.
**The Stables can accommodate flexible check in days – please contact us to request.** Located in the famous Blackdown Hills near the Somerset and Devon border you will find The...
7 nights from £837
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £829 booking fees included
Florian
5939Dog friendly converted shipping container with outdoor bath tub near Cheddar.
This bijou beauty is just perfect for romantic getaways or for solo travellers seeking to escape the everyday. A stunning converted shipping container, it boasts idyllic countrysid...
7 nights from £829
Wheelwrights Cottages
7 nights from £1383.83 booking fees included
7 nights from £692 * booking fees included
The Smithy
58322 bedroom, dog friendly holiday cottage near Glastonbury, Somerset.
If a stunning conversion bursting with original features situated in a sleepy Somerset village sounds attractive then The Smithy is the place for you. Situated in close proximity t...
7 nights from £692 *
7 nights from £2015 booking fees included
Merryfields
55724 bedroom, dog friendly self catering cottage near Bath.
This spacious detached Victorian house is set on a two acre site in the rural village of Colerne, occupying a spectacular position over Box Valley with views of Salisbury Plain in ...
7 nights from £2015
7 nights from £942 booking fees included
The Cottage at Ford Barton
54672 bedroom cottage in the Blackdown Hills near Wellington, Somerset.
Within the pretty Somerset village of Churchinford, this tranquil cottage has been furnished with comfort in mind. There is so much to explore locally with the Blackdown Hills Nati...
7 nights from £942
7 nights from £539 * booking fees included
Pippins
53602 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 £539 *
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.
If you are not quite ready to let summer go yet, book yourself a September holiday in Somerset. Last-minute or planned well in advance, a September getaway in Somerset will let you do your summer justice and leave you feeling relaxed and revived. Whether you are looking for a one-bed retreat, dog-friendly holiday cottage or big house with space enough for all the family and friends too, we will help you find the right cottage for you. With every one of our holiday cottages personally inspected and carefully selected onto our books, we make sure you can enjoy the best of the best. Browse our 32 cottages available for a September break in Somerset and let the good times commence. Your holiday with Classic Cottages will be so good you'll wish you could do it twice.
