Portland Cottages

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    • Sleeps5
    • Bedrooms3
    • PetsNo

    A modern terraced house on Portland, sleeps 5, close to Portland Bill. Sea views and coastal footpaths on the doorstep. Short walk to shops, WiFi. (Ref. 994573)

    Last booked yesterday

    7 nights from £516

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    Located on the Isle of Portland, with plenty of walks and views to enjoy. Two well behaved dogs welcome. (Ref. 994520)

    7 nights from £418

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    A beautiful stone cottage, complete with garden on the quieter end of Portland, however situated on the main bus route to Weymouth and beyond. (Ref. 994021)

    7 nights from £417

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    • Sleeps5
    • Bedrooms3
    • PetsYes

    A stone Fisherman's cottage on Portland, WIFI, ideal location for exploring Portland, sail at the National sailing academy and the Jurassic Coast. (Ref. 993918)

    7 nights from £488

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    • Sleeps8
    • Bedrooms4
    • PetsYes

    A Portland house with Stunning views, sleeps 8, tucked away in a private road, parking for 3 cars, close to the national sailing academy, (Ref. 994554)

    7 nights from £653

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    • Sleeps6
    • Bedrooms3
    • PetsNo

    Bright contemporary property perfect groups of guests in the Isle of Portland. Sea views. WiFi. Shop 10 min. Pub 5 min. Beach 5 min. Weymouth 4.9 miles. (Ref. 994754)

    7 nights from £634

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    • Sleeps6
    • Bedrooms3
    • PetsNo

    Three bedrooms on Portland, moments from Chesil beach. Balcony overlooking sea and coastline. (Ref. 994701)

    7 nights from £516

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    • Sleeps5
    • Bedrooms3
    • PetsYes

    Neptune cottage situated in the Isle of Portland is very cosy and comfortable. Perfect for fog walks. Beach 2 min. Welcomes two dogs. Pub 5 min, shop 10 min. Weymouth 5 miles. (Ref. 994425)

    7 nights from £465

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    Traditional cosy terraced cottage on Portland, close to Chesil Beach, WIFI, parking for one car. Close to Portland Bill and Weymouth. (Ref. 994744)

    Last booked yesterday

    7 nights from £445

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    Situated in the Isle of Portland, Langham Cottage is very comfortable and spacious holiday home. Accepts one dog. Pub and shop 5 min. Beach 5 min. Bridport 23 miles. (Ref. 994321)

    7 nights from £431

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We have a wide variety of self-catering holiday cottages on the wonderful Isle of Portland, from modern contemporary lodges overlooking the sea, to old stone cottages in charming village locations, stunning harbour side properties with unrivalled sea views and luxurious holiday homes, just a stone’s throw from the beautiful Jurassic coast.

Portland is a wonderful holiday destination. It offers arguably the best sailing and windsurfing waters in the world, an abundance of rare wildlife since Portland is a major migrating point for birds, miles of stunning coastal walks, great fishing trips straight from Portland Marina, beautiful beaches, some of which are dog friendly all year around, fantastic pubs and some of the best cream teas in Dorset.

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.

Meander through the pretty villages filled with old stone cottages, cobbled streets, traditional shops and cafes and stop for cream tea and lashings of luscious cake. The main village of Portland is Easton, which sits on the plateau. Then there is Fortuneswell, which lies on a steep hill and was described by Thomas Hardy as being ‘houses above houses, one man’s doorstep rising behind his neighbour’s chimney’. Southwell is another charming village, filled with quaint quarrymen cottages and a village pub in the heart of the village. Park here to access the glorious cliff walks along the South West Coastal Path.

Portland Attractions

Portland Bill Lighthouse and Visitor Centre

If you are staying in a Portland holiday cottage, you will pass by the iconic red and white striped lighthouse on the southernmost tip of Portland which features on many a Dorset postcard. Portland Bill Lighthouse is a must see for all Portland holiday makers. The visitor centre has had a huge amount of money spent on it in recent years to make it all the more exciting for children (and adults). Let them experience a stormy sea journey in the ‘Into the Dark’ interactive zone and then all climb the lighthouse tower and take in the views for miles and miles, along the stunning Jurassic coastline. From here you get the best view of the Portland Race too, which is the treacherous part of the sea for vessels and the reason why the Portland Bill Lighthouse is still a working lighthouse today.

Portland Castle

Portland Castle, overlooking Portland Harbour was constructed under Henry VIII in the early 1540’s to defend the south coast against the ever-present threat of French and Spanish invasion.

Walk along the gun platforms and look out to the beautiful Dorset seas. Meander through the Contemporary Heritage Garden, see inside the Tudor kitchen and then eat cake in the Captain’s Tearoom. A lovely day out for all!

Portland Museum

Portland Museum is in two beautiful early 17th century stone cottages, just above the cove at Church Ope, housing many old pieces associated with the history of the island. Thomas Hardy used one of the cottages as inspiration for the home of one of the heroines in his novel ‘The Wellbeloved’.

Church Ope Cove

Church Ope Cove is an idyllic little beach, used by the locals and dog friendly all year round. Be warned, there are quite a few steps which you need to take to get to it! If you walk down through the old church graveyard, be sure to look out for the graves of the pirates!