Vacation rentals in Osmington

The Annex @14

Welcome to The Annex @14, a newly renovated ground floor property and great base for exploring historic Dorset and a perfect getaway for two! Self-contained with its own private entrance .The annex is attached to our home at the end of a quiet cul-de-sac in the village of Crossways near Dorchester. There is a hot tub available for your own exclusive use! In the heart of Hardy Country, ideal for walkers and cyclists. Lulworth Cove, Durdle Door, the beautiful sands of Weymouth Bay are close by.

The Old Reading Room West Stafford

The Victorian Reading Room of West Stafford is of historical importance. Used before the war as a Reading Room for the villagers and estate workers, the newspapers were provided, the village shop in the late 1930s, then a workshop and a store room for the church. We have now lovingly restored, decorated and furnished this amazing building into a cosy self catering holiday retreat, "far from the madding crowd" Open plan, comfy double sofabed, wood burner, country walks and fabulous village pub.

Discover Little Drey: Your Perfect Getaway

At Little Drey, you'll find comfort, and warm hospitality, all while being conveniently close to Dorchester. A variety of restaurants, cafes, and shops are all within walking distance. Close to some of the best places to visit in Dorset, and within easy reach of famous beauty spots and amazing places to visit. Parking on property along with self-check-in, makes it super easy to have a relaxing, enjoyable break. Your host lives next door and is on hand to make your stay the best possible.

Old Dorset Cottage

Relax with the whole family in this peaceful traditional Dorset Cottage. Set in the tranquil village of Osmington, this Cottage has all the traditional features with the exposed stonework, beams and large inglenook fireplace. It has been tastefully modernised to make it fit for a family get away. With a new kitchen, large farmhouse dining room and all facilities to help you feel right at home. Outside enjoy the gardens, bbq and patio and easy access to country walks and beaches.

Live the coastal cottage dream in Dorset AONB

Welcome to Heather Cottage – the charming coastal retreat you've been dreaming of! With its idyllic pink doors and picture-perfect cottage appeal, it's everything you could want in a coastal getaway. If you've ever imagined living the coastal cottage dream, this could be your perfect escape. Just like us, when my partner and I were searching for our first home, now, we're thrilled to share its beauty with you. Come and make your own memories here – we can't wait to welcome you!

Coppice Barn, farm stay, nr Durdle Door & Lulworth

Sorry no Pets Suitable for only one infant. A barn conversion two miles from the South Dorset Coast. Set within its own private garden with unspoilt views of Galton Farm overlooking Moreton forest and Tadnoll Heath. Ten minutes drive to Durdle Door, Lulworth Cove and Ringstead Bay. Plenty of coastal and country walks to choose from. The barn consists of one bedroom with a superking bed. Large bathroom and open plan kitchen, dining and sitting area all delightfully decorated.

Beautiful Annex situated on the Jurrasic Coast.

Pixon Barn is situated on a working farm on the Jurassic Coastline within an easy driving distance to Weymouth, Lulworth Cove, and Abbotsbury. It is located next to numerous bridlepaths, perfect for avid walkers, cyclists and lovers of the countryside. We welcome any and all well behaved dogs. There are several pubs all within a 5 minutes distance by car, as well as our own farm cafe and shop located on the main road into Weymouth. Best ice-cream around.!

The Condo (Indoor Pool available May- end Sept)

Self contained detached cottage in a tranquil location close to the famous 'Jurassic Coast' ; Durdle Door, Lulworth, Corfe Castle, Weymouth and Dorchester are all a short drive away. Further attractions close by are Monkey World, Bovington Tank Museum, and Sculpture by the lakes. There is a well stocked village shop and good village pub. Dorset has so much to offer, with beautiful coastline and breathtaking scenery. Relax in the pool at your leisure!

Luxury Cottage with Copper Bath and Scenic Trails

Escape to Granary Cottage – a romantic one-bedroom hideaway in the Dorset countryside. Soak in the copper bath after days exploring dramatic coastal cliffs, hidden coves and rolling hills. With walking trails from the door and the South West Coast Path moments away, adventure is never far. After a day outdoors, retreat to your cosy, stylish space made for two. A perfect blend of rustic charm, comfort and wild beauty.