Book Luxury Holiday Rentals in Osmington Mills

Award-winning homes from £98

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Home spotlights in Osmington Mills

The Bunker

The Bunker

  • 6 guests

  • 3 bedrooms

Osmington, Dorset

Originally built as a bunker for the RAF in 1941 and decommissioned in 1956, this truly remarkable home has been thoughtfully redesigned with its Grade II listing in mind. Retaining its original concrete walls as well as a range of other elements, this is a home you won’t soon forget – offering three bedrooms, two bathrooms and surrounded by the picturesque Dorset countryside, it’s simultaneously idyllic, modern and historic.

A Cottage by the Sea

A Cottage by the Sea

  • 4 guests

  • 2 bedrooms

Osmington, Dorset

If you love history, this former transmitter bunker serving RAF Ringstead during the Second World War will really appeal. Now a Grade-II listed home, it has stunning views over the sea from both the south-facing terrace and the living space.

Little Butterflies

Little Butterflies

  • 7 guests

  • 3 bedrooms

Dorchester, Dorset

Nestled on the water’s edge, this home has relaxation at its core. Inside is comfortable and homely, while the outdoor space boasts decking and opportunities for alfresco dining – all while enjoying the lake views, naturally.

Bowleaze Breeze

Bowleaze Breeze

  • 7 guests

  • 4 bedrooms

Preston, Dorset

With three pubs just moments away, as well as convenience stores, you'll have everything you need for a comfortable stay. This home is also just a stroll from Bowleaze Cove and a short drive from Weymouth with its bustling harbour and sandy beaches.


We selected the top 3% holiday homes in Osmington Mills Holiday Rentals

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Most popular homes in Osmington Mills

Rose of the Heart

Rose of the Heart

  • 6 guests

  • 3 bedrooms

Winfrith Newburgh, Dorset

Coastal Romantic

Coastal Romantic

  • 2 guests

  • 1 bedrooms

Weymouth, Dorset

Brine & Brew

Brine & Brew

  • 4 guests

  • 2 bedrooms

Weymouth, Dorset

Dorset Darling

Dorset Darling

  • 10 guests

  • 5 bedrooms

Dorchester, Dorset

Ocean & Beach Views

Ocean & Beach Views

  • 2 guests

  • 1 bedrooms

Weymouth, Dorset

Jurassic Coast Hideaway

Jurassic Coast Hideaway

  • 5 guests

  • 3 bedrooms

Osmington, Dorset

Marble & Charcoal

Marble & Charcoal

  • 12 guests

  • 6 bedrooms

Weymouth, Dorset

The Piazza

The Piazza

  • 4 guests

  • 2 bedrooms

Dorchester, Dorset

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Osmington Mills. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Osmington Mills has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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