Cottages for a five night break in Dorset
We have an exclusive handpicked collection of luxury cottages available for you to enjoy that precious time away in Dorset, so pick your next escape and get ready for a five night adventure. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 37 cottages available in Dorset available for five night breaks
7 nights from £1050
Hood's
60452 bedroom, dog friendly self catering cottage near Bridport, Dorset.
This stunning barn and milking parlour conversion is set within the glorious Dorset countryside, offering panoramic views across the Marshwood Vale and beyond. Hood's provides luxu...
7 nights from £1050
7 nights from £578
Loaf
60461 bedroom, dog friendly self catering cottage near Bridport, Dorset.
Loaf is a gorgeous and sympathetic restoration of an ancient Dorset granary with panoramic views across the Marshwood Vale. Its interiors are straight out of a magazine with design...
7 nights from £578
7 nights from £555 *
Freshfields
57064 bedroom self catering cottage near Dorchester, Dorset.
Freshfields is a truly outstanding property in a picturesque Dorset village. Recently renovated throughout, the house provides space and privacy for all the family. Just a short dr...
7 nights from £555 *
7 nights from £495 *
Bluebells
56242 bedroom, dog friendly cottage in walking distance of Bridport, Dorset.
Tucked away in a quiet location, yet just a stone's throw from bustling Bridport and the Jurassic Coast, you will find Bluebells. Situated at the end of a pretty row of cottages, t...
7 nights from £495 *
7 nights from £752
The Old Dairy
55512 bedroom, dog friendly cottage near Wimborne Minster, Dorset.
Situated within the southern neolithic ring of Knowlton Church and Earthworks and perfectly positioned under a Dark Sky Reserve, is The Old Dairy; a stylish and modern conversion t...
7 nights from £752
7 nights from £392 *
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 £392 *
7 nights from £472 *
Woodville Cottage
51513 bedroom, dog friendly home near the beach in Lyme Regis.
Woodville Cottage is a pretty and charming property, an annexe to a Grade II Listed Georgian building. Hidden away from the hustle and bustle of the elegant seaside town of Lyme Re...
7 nights from £472 *
7 nights from £1093
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 £1093
7 nights from £556 *
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 £556 *
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20% off
17 Oct 2025 - 24 Oct 2025
From £597.00 £477.60
7 nights from £462 *
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. As you pull into the spacious parking-area you will get ...
7 nights from £462 *
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20% off
20 Oct 2025 - 27 Oct 2025
From £462.00 £369.60
A five night break in the UK allows you the opportunity to extend your short break just that little bit longer, giving you that much desired extra time to explore the area, unwind a little more and make the most of your time off. With gorgeous properties in Cornwall, Devon, Somerset, Dorset, Sussex and the Isle of Wight, you have plenty of options to choose from...
