Portland Cottages

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Your search returned 35 cottages.

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  • The Old Police Station

    Fortuneswell, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo
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    The Old Police Station is a fantastic house residing in Fortuneswell, Dorset. (Ref. 1082042)

    7 nights from £913

    Last booked yesterday
    Book now
  • The Shambles

    Fortuneswell, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    A well-presented two-bedroom cottage resting in Fortuneswell in Dorset. (Ref. 1082838)

    7 nights from £594

  • Sunrise Hill

    Castletown, Portland, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo
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    Sunrise Hill is a well-presented, modern apartment in Castletown on the beautiful Isle of Portland. (Ref. 1079649)

    7 nights from £403

  • Smallmouth Cottage

    Wyke Regis, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    A charming two-bedroom terrace house resting in Wyke Regis, Weymouth. (Ref. 1073525)

    7 nights from £647

  • Portland View

    Portland Bill, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    A beautifully presented apartment with stunning views across the bay and Portland Bill. (Ref. 1070193)

    7 nights from £494

  • Tidal Drift

    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes
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    A delightful, mid-terrace home just moments from the beach in the village of Wyke Regis, Weymouth. (Ref. 1071852)

    7 nights from £599

  • Osprey House Portland

    Portland, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo
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    Detached, large and modern house for large group of friends or big family. (Ref. 994499)

    7 nights from £634

  • St Johns View

    Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    St. (Ref. 994677)

    7 nights from £510

  • Jurassic Coast House

    Portland, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsYes
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    Modern and comfortable holiday house for up to 8 people in the Isle of Portland. (Ref. 994310)

    7 nights from £832

  • For Your View Only

    Portland Bill, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes
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    A spacious apartment with stunning views to sea and Portland Bill. (Ref. 1001824)

    7 nights from £555

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Our properties on the wonderful Isle of Portland range from modern contemporary lodges overlooking the sea to stunning harbourside properties with unrivalled sea views, just a stone’s throw from the beautiful Jurassic Coast.

Portland itself offers arguably the best sailing and windsurfing waters in the world, equipped with an abundance of rare wildlife, miles of stunning coastal walks and a beautiful marina to facilitate great fishing trips. Portland also plays host to beautiful beaches, some of which are dog-friendly all year round, fantastic pubs and some of the best cream teas in the whole of Dorset.

Portland Holiday Cottages

Our Portland holiday cottages are equally perfect for those wishing to enjoy the great outdoors, as well as those wishing to cosy up with stunning views right outside their cottage windows.

Our cottages sleep parties of all sizes, as well as many accommodating dogs and young children. Stay in the heart of Portland itself or stay in the surrounding area to bask in the beauty of the Dorset coast.

Places to visit near Portland

If you're looking to venture outside of Portland during your stay, then you won't be short for choice. With many other Dorset favourites just a short drive away, you can explore the likes of Chesil Beach and the Jurassic Coast in a day. Locations such as Abbotsbury, Osmington, West Bexington, Chesil Beach, West Lulworth and Weymouth are just as beautiful as Portland and offer all sorts of different attractions and days out.

Start your Portland adventure today by chatting to one of our helpful travel experts or continue browsing our secure website.