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Osprey Holiday Cottages

Portland, Dorset

  • Osprey Holiday Cottages
  • Osprey Holiday Cottages
  • Osprey Holiday Cottages
  • Osprey Holiday Cottages

31 Easton Square Portland, DT5 1BU

Tel: 01305 818118

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Holiday accommodation in Weymouth & Portland.

Choose from our hand-picked self-catering holiday accommodation, from country cottages to luxury bolt-holes - all set in the spectacular location of Weymouth & Portland in the heart of the Jurassic Coast.

Find out more by viewing and booking online at www.ospreycottages.co.uk, by emailing us at hello@ospreycottages.co.uk or by calling 01305 818118!

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Latest Portland Features

10 Nov 2025
Father Christmas Visits Dorset Whether you call him Santa Claus, Father Christmas, St Nicks or simply Santa, your little one will want to meet the real Santa in Dorset this year. Lucky for you, many of Dorset's businesses have arranged magical experiences and Santa's Grottos throughout Dorset for you and your family to do just that. Maybe you're looking for breakfast with Santa, a magical winter wonderland, or a SEN Santa visit. We are building up all the best local events, so take a look at ... Read more...
9 Nov 2025
Christmas Shopping in Dorset You'll find the perfect present while Christmas shopping in Dorset, find unique gifts, local art, Dorset food and drink and much more. We've put together a few ideas to help get you started! 1 – Have you got a tank enthusiast in the family? Take a look at the Tank Museum online shop: from baubles to model kits and themed T-shirts, their shop has something for everyone. 2 – Looking for some foodie gifts this ... Read more...
4 Nov 2025
Towns of Culture - Reveal Portland & Weymouth Portland & Weymouth Revealed! Reveal - Portland & Weymouth Towns of Culture 2025 is a celebration of the vibrant cultural scene in Portland and Weymouth. Showcasing the rich tapestry of artistic expression, local talent, and diverse events that define the two towns. Join in, exploring the unique stories, traditions, and creativity that make Portland and Weymouth the cultural gems of 2025. What to expect! Thanks to funding from the Arts Development Company, Portland ... Read more...
8 Oct 2025
Half-term Events in Dorset So, it’s the October half term and you may be wondering how you’re going to keep the kids entertained! Well don’t worry, whether you are local resident or are staying in Dorset on a break, there’s lots to do throughout the half term holidays. If you're looking for things to do in Dorset we have found lots of Dorset events to keep you entertained. Our Resort family has children of different ages, here are some of the things we plan to enjoy during the ... Read more...
1 Sep 2025
Portland Bill Lighthouse Tour Iconic, Historic, with a Touch of Romance – Portland Bill Lighthouse Portland Bill - Scoop of Dorset As a local Weymouth girl, I’ve always admired Portland Bill Lighthouse. Our Resort offices were once within striking distance of this iconic landmark, yet until last week I had never climbed to the top. Over the years I’ve walked around its base, picnicked on the rocks, watched winter storms roll in, dined at the Lobster Pot, and shared countless memories with ... Read more...

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