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
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 46 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.
Select from 46 Somerset cottages available for September
7 nights from £516
Hayloft
24032 bedroom dog friendly holiday cottage near Ilminster, Somerset.
Hayloft is in the heart of Barrington near the historic market town of Ilminster in south Somerset. This welcoming barn conversion is within a small group of historic barns and ...
7 nights from £516
7 nights from £669
Bumble Bee Barn
23802 bedroom, rural holiday cottage with a hot tub, near Taunton, Somerset.
Set in the vale of Taunton, halfway between Exmoor National Park and the beautiful Quantock Hills and an easy drive from the coast, this is a perfect base from which to discover th...
7 nights from £669
7 nights from £583
The Pump House
20981 bedroom, dog friendly holiday cottage near Beaminster, Dorset.
Seize a unique opportunity and book a stay in this stunning converted pump house on the Somerset/Dorset border, close to the dramatic beaches and clifftop walks of the Jurassic Coa...
7 nights from £583
7 nights from £412 *
Cleveland Cottage
19682 bedroom cottage near the market town of Dulverton, Somerset.
Offering a 20% discount for parties of 2 (unless a special offer is already in place), this pretty cottage is situated on the eastern edge of Exmoor National Park, which can make i...
7 nights from £412 *
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20% off
24 May 2024 - 31 May 2024
£782.00£625.60
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 £479
Week Cottage
16361 bedroom, rural dog friendly cottage near Dulverton, Somerset.
Sitting in the heart of Exmoor National Park, Week Cottage dates back to the 1690s and is all picture-book old world charm inside. A spacious boot-room, perfect for muddy boots (an...
7 nights from £479
7 nights from £641
Manor Farm Lodge
16162 bedroom, dog friendly holiday cottage near Beaminster, Somerset.
Manor Farm Lodge is situated on the Somerset/Dorset border, with easy access to Devon. This beautifully presented cottage, surrounded by its traditional cottage garden, is the idea...
7 nights from £641
