Portland Holiday Cottages

Find your perfect Portland holiday cottage including pet-friendly Portland holiday cottages. Whether you are looking for a romantic break or a family holiday, we have a great collection of cottages to choose from.
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Boatswain’s Watch - Fortuneswell

Boatswain’s Watch is a lovely semi-detached Victorian cottage resting in Fortuneswell, Dorset. Hosting two bedrooms: one double and one single with a pull-out bed, together sleeping up to four guests....

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £381
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The Chesil Lookout - Fortuneswell

The living areas in the property consist of a kitchen with an oven, hob, microwave, fridge, washing machine, tumble dryer, dishwasher, dining room with seating for 12 people and a...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £1326
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Sea Gem - Castletown

The living areas in this three-storey property include a kitchen/diner with an electric double oven and grill, gas hob, microwave, fridge/freezer, washer/dryer, dishwasher, coffee machine, breakfast bar for four, and...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £789
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Panoramic View - Castletown

Located on the rugged and beautiful Isle of Portland, Panoramic View is a well presented, modern apartment benefiting from an onsite indoor swimming pool and gym. This bright and airy...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £423
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Sunrise Hill - Castletown

Sunrise Hill is an excellent apartment perched on the coast in Castletown, Portland. Hosting one double bedroom, along with a bathroom, this property sleeps up to two guests. There is...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £364
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Sunset Lodge - Fortuneswell

Sunset Lodge is a modern contemporary apartment situated in Fortuneswell in Portland in Dorset and benefits from the sea-facing balcony. The cottage can sleep 6 people in 2 king-size double...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £486
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Schooner Cottage - Chiswell

Schooners Cottage is a refreshing Georgian terraced cottage set in the quaint village of Fortuneswell, Dorset. Hosting three bedrooms: one first floor double, one second-floor double and one second-floor day...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £465
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Jurassic Coast House - Fortuneswell

Located in a stunning residential development, The Officer’s Field, Jurassic Coast House was originally built to house athletes during the 2012 Olympic sailing events and situated on the edge of...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £751
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St Johns View - Fortuneswell

St Johns View is a contemporary detached house situated in Fortuneswell in Portland in Dorset with sea views. The house can sleep 4 people in a king-size double with en-suite...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £417
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Neptune Cottage - Fortuneswell

Neptune Cottage is a traditional Portland cottage situated in Fortuneswell, Portland, Dorset and benefits from its location on Chesil Beach. The cottage can sleep 5 people in 1 double, 1...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £444
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Charlton House - Easton

Charlton House situated on the Isle of Portland near Weymouth in Dorset can sleep six people in three bedrooms, 2 x double and 1 x twin and a family bathroom....

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £496
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Cytringham - Southwell

The living areas in this mid-terraced property consist of a kitchen with an electric oven, gas hob, microwave, fridge/freezer and washing machine, a living/dining room with Smart TV and electric...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £495
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