Weymouth Cottages
A town of two halves - the old town forms a cluster of quirky mismatched cottages around the harbour, while the new town is an elegant parade of Georgian town houses on the seafront.
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 16 self catering cottages in Weymouth to show you...
7 nights from £730
Halcyon Cottage
46932 bedroom cottage close to the beach, Lulworth Cove and Dorchester, Dorset.
Less than two miles from Lulworth Cove, part of the only World Heritage Site in England, Halcyon Cottage is a pretty, detached stone cottage in the heart of the village of West Lul...
7 nights from £730
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25% off
15 Aug 2025 - 22 Aug 2025
From £1358.00 £1018.50
7 nights from £490
Beehive Cottage
40732 bedroom thatched, dog friendly cottage near Dorchester, Dorset.
Beehive Cottage is a charming and cosy cottage, on a quiet lane opposite St Mary's church in the village of Puddletown. Surrounded by farmland, the pretty village is nestled in the...
7 nights from £490
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 £639
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. From the moment you pull into the driveway you will love...
7 nights from £639
7 nights from £583 *
Tolpuddle Cottage
37523 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.
This pretty thatched cottage is in the tranquil historic village of Tolpuddle, just 15 miles from the World Heritage Jurassic Coast. An ideal base for a family holiday or perfect f...
7 nights from £583 *
7 nights from £415 *
Sturthill Stable
28293 bedroom, dog friendly barn conversion set within a working farm near Bridport, Dorset.
This beautiful barn conversion at the heart of a working farm is just inland from Dorset's spectacular Jurassic Coast and its beaches. The rural setting will please all the family ...
7 nights from £415 *
7 nights from £599 *
Barn Owls Cottage
30153 bedroom, dog friendly cottage near Bridport, Dorset.
Barn Owls Cottage is a semi-detached cottage that has been converted from an 18th Century stone barn. Despite having stylish modern fittings, it has still retained much of its orig...
7 nights from £599 *
West Hembury Farm
7 nights from £1017
7 nights from £419
Badgers Cottage
30141 bedroom, dog friendly cottage near Bridport, Dorset.
This pretty semi-detached cottage for two is nestled within an Area of Outstanding Natural Beauty (now known as National Landscapes) on West Hembury Farm. Badgers Cottage is an ...
7 nights from £419
Each and every one of our cottages is fully equipped with everything you’ll need on holiday.
Fully equipped cottages
All of our cottages have a standard list of equipment that goes above and beyond. As well as fluffy towels and readymade beds, our bare minimum includes everything you’ll need and more, from plenty of teaspoons to added extras such as gravy boats so no matter where you stay, you’ll be able to make your favourite home-cooked dishes.
Each inventory is regularly checked and counted so you won’t be stuck without a ladle and can leave your hairdryer at home, plus you’ll find a starter set of toiletries and cleaning products so you can get on with your holiday.
7 nights from £529
Ivy Cottage
41222 bedroom, dog friendly cottage in Cattistock near Dorchester, Dorset.
Imagine life in a tranquil Dorset village and Ivy Cottage is just the sort of place you may picture in your mind. Set in the midst of a National Landscape, the cottage is situated ...
7 nights from £529
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20% off
18 Jul 2025 - 25 Jul 2025
From £1005.00 £804.00
7 nights from £969
Beech Cottage
28875 bedroom, dog friendly cottage with views over the nature reserve near Bridport, Dorset.
This beautiful stone farmhouse has something very special indeed - it comes with a 450 acre nature reserve and a unique relationship with Dorset Wildlife Trust, offering comfortabl...
7 nights from £969
