Osmington Cottages

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Cosy seaside house with balcony in Preston, Dorset. Perfect for a small family or couples. WiFi. 30 mins walk to Weymouth. Two minute walk to the beach. (Ref. 994045)

    Last booked less than an hour ago

    7 nights from £516

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Lovely holiday home in Preston, South Dorset. Suitable for couples or small family. Wifi. Seaviews from the patio. Beach and pub 5 mins walk. Weymouth 2 miles. (Ref. 994026)

    7 nights from £488

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    Two bedrooms: 1 x ground floor twin single, 1 x double with en-suite with shower over, basin and WC. Ground floor shower room with basin and WC. Open plan kitchen with dining area and sitting area. (Ref. 994702)

    7 nights from £488

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Located close to the coast, this holiday home is perfect for a romantic retreat or small family holiday. Having sea views, a stones throw from the beach. Walking distance to the main town centre. Off road parking. Wifi. (Ref. 994645)

    7 nights from £488

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    • Sleeps6
    • Bedrooms3
    • PetsNo

    Situated in the beautiful Bowleaze Cove area of Weymouth, just seconds from a beach is this enchanting holiday home. (Ref. 994020)

    7 nights from £697

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    A modern ground floor annex in Weymouth, just moments from the beach. 1 well behaved pet, WiFi, parking for two cars. (Ref. 994726)

    Last booked yesterday

    7 nights from £516

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    A completely renovated contemporary bungalow in a quiet residential area with sea views, wood burner, Wifi, Welcomes 2 well behaved dogs. (Ref. 994501)

    7 nights from £465

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    Lovely early Victorian style Grade II listed cottage set in Warmwell village. Sleeps four guests. Garden. Welcomes two small dogs. Pub 3 miles. Shop 2 miles. Dorchester 6 miles. (Ref. 994760)

    7 nights from £449

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The seaside village of Osmington is home to some of our prettiest self-catering Dream Cottages. The picturesque country lanes are filled with beautiful thatched old stone cottages and farm houses and the network of country walks throughout the village, ensure that you have the best walking routes right on your doorstep.

Some of our Osmington cottages include thatched farm cottages, a 300 year old traditional slate roofed cottage, old characterful cottages with wood burning stoves or open fires as well as a modern converted lodge. The location of these properties is such that you can enjoy a really peaceful countryside break by the sea, yet you are so close to the bustling towns of Weymouth and Dorchester.

The village of Osmington itself is the quintessential English village. With its own free range dairy farm and tea room (which actually offers ‘Doorstep Delivery’s’ if this interests you) and a couple of great local pubs, there is always somewhere to rest after your countryside walk or village meander.

The Smugglers Inn, marks the halfway point on the South West Coastal Path between The Durdle Door and Weymouth so there are plenty of sights to behold on route. The pub is also just a 20 minute walk east to Ringstead Bay, where the sea is so calm and beautiful that it makes it the perfect place to launch your canoe or kayak.

Use your Osmington cottage as a base and explore the Jurassic coast. There are some fantastic fossil walks, whether organised by a company or adventured solo. The 195 million year old history stamped into the Jurassic Coast is what makes this area so wonderful. Dorset was tropical and in the centre of the giant Pangaea continent back then so any fossils found today from this time, have not been touched by a living thing for 195 million years, which is pretty incredible and the ease at which you will find complete ammonite fossils in this area makes for an extremely rewarding day.

Osmington Mills

The small but perfectly formed village of Osmington Mills is nestled in a small cove on the edge of the coast. With coastal paths and countryside walks in abundance, this spot is perfect for those seeking a peaceful getaway to one of the most beautiful parts of the country. Osmington Mills is home to The Smugglers Inn pub mentioned above. It is super dog friendly with a delicious menu and some great tales of the infamous smugglers who would have drunk tankards of ale there many moons ago. If you are staying in one of our Dream Cottages anywhere near Osmington Mills, then this pub should definitely form a resting point during one of your rejuvenating walks.

Osmington Mills Beach

Osmington Mills Beach is a hidden piece of paradise, favoured by the locals, as well as those who may not want the full Punch n Judy Show action found on Weymouth Beach, down the road. The beach is a mix of large rocks and pebbles, with patches of sand and rock pools in between. Perfect for picnics since the flat rocks can hold your glasses of wine just perfectly and crabbing in the rock pools will keep the youngsters entertained for hours. It’s a great beach for swimming too although footwear is advised, to make it more pleasurable.

Have a browse though some of our prettiest cottages and find one that suits you. Some are dog friendly too so make sure you check before booking!