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Our featured holiday lets in Weymouth & Portland
A hand-picked selection of quality self-catering holiday accommodation including houses, apartments and more...
Featured
From £115/night
Dory Cottage
Fortuneswell, Portland, Dorset, United Kingdom- 3 Bedrooms
- 2 Bathrooms
- 5 Guests
- Houses
Featured
From £110/night
Portland View
Southwell Park, Portland, Dorset, United Kingdom- 2 Bedrooms
- 2 Bathrooms
- 4 Guests
- Apartments
Featured
From £137/night
Vindelis Cottage
Chesil Mews, Chesil Beach, Portland, Dorset, United Kingdom- 2 Bedrooms
- 1 Bathrooms
- 4 Guests
- Houses
Featured
From £160/night
Stone’s Throw
Old Harbour, Weymouth, Dorset, UK- 3 Bedrooms
- 2.5 Bathrooms
- 6 Guests
- Houses
Featured
From £220/night
Sally Hall House
Easton, Portland, Dorset, UK- 4 Bedrooms
- 2.5 Bathrooms
- 9 Guests
- Houses
Featured
From £150/night
Quayside Apartment
Atlantic House, Castletown, Portland, Dorset, UK- 3 Bedrooms
- 2 Bathrooms
- 6 Guests
- Apartments
Why Osprey Holiday Cottages?
Hand-picked holiday cottages & lets
All of our holiday cottages & lets are hand-picked and regularly inspected giving you peace of mind
Find my holiday letManaged by a local team - 7 days a week
We're based where we offer holiday rentals so we know our surroundings and if you need us, we're never far away
Get in touch with usWe're looking for hosts & owners
Our portfolio is growing, but we're still looking for more of the right type of holiday properties. Talk to us today!
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