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 1323 holiday cottages available in September
7 nights from £743 *
The Barn at Newton Creek
60553 bedroom, dog friendly cottage with estuary views in Newton Ferrers.
Escape to the spellbinding haven of The Barn at Newton Creek, a truly enchanting waterside retreat where time slows, hearts rest, and nature whispers its secrets. Set in an enviabl...
7 nights from £743 *
7 nights from £858
Plain An Gwarry
60644 bedroom, dog friendly cottage near Mevagissey, South Cornwall.
Nestled in the heart of the glorious Cornish countryside on the outskirts of the pretty village of St Ewe, close to the fabulous beaches of Gorran Haven and Mevagissey, Plain An Gw...
7 nights from £858
7 nights from £1200
Vanilla Skye
59431 bedroom self catering cottage with sea views near Portree.
Vanilla Skye is set in the most idyllic of locations overlooking the loch and mountains beyond. It is an ideal bolthole for couples looking to get away from it all and having a per...
7 nights from £1200
7 nights from £725
Pomona Annexe
60532 bedroom, dog friendly self catering cottage in Battle.
Located just a short drive from the stunning Sussex coast and a short ten-minute walk to the RSPB Fore Wood Nature Reserve and the iconic town of Battle, Pomona Annexe is a charmin...
7 nights from £725
7 nights from £1187 *
Rosmelin
60593 bedroom, dog friendly cottage near Wadebridge, North Cornwall.
Nestled in the heart of the Cornish countryside, Rosmelin is a truly stunning hideaway that invites you to wrap yourself in the lap of luxury and be embraced by the peace and calm ...
7 nights from £1187 *
7 nights from £840
The Byre
60661 bedroom self catering cottage near Taunton, Somerset.
Located in the picturesque Blackdown Hills near the Somerset and Devon border you will find The Byre. A one bedroom converted cowshed which combines original character with modern ...
7 nights from £840
7 nights from £840
The Stables
60651 bedroom self catering cottage near Taunton, Somerset.
Located in the famous Blackdown Hills near the Somerset and Devon border you will find The Stables. A luxurious one bedroom converted stable which combines original character with ...
7 nights from £840
7 nights from £1549 *
Higher Trennal Farm
60234 bedroom, dog friendly holiday cottage near Penzance, West Cornwall.
Step back in time at Higher Trennal Farm, an historic Cornish home dating back to 1740. Once known as Trenwall, this characterful farmhouse has been lovingly rebuilt and restored o...
7 nights from £1549 *
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25% off
22 Dec 2025 - 29 Dec 2025
From £2020.50 £1515.38
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
Palm Villa
179Palm Villa is a spacious town house just minutes from the beach
Ideal for families or groups of friends, Palm Villa is a tall, traditional 3 bedroom house, recently refurbished to a modern standard. A spacious open plan kitchen, dining and livi...
Seaspray
180Luxury beachfront retreat with panoramic sea views.
Seaspray is a luxurious 4-Star Gold self-catering retreat set right on the beach at Port Erin. Beautifully renovated throughout, this contemporary coastal haven combines comfort an...
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.
