Portland Holiday Search

Find your perfect Portland Cottage

Read more

Alpen Rose Cottage - Easton

A restored traditional fisherman’s cottage situated on the Isle of Portland.

  • From £458
Read more

Quarr Cottage - Wakeham

Quarr Cottage is a traditionally-styled cottage sitting in the hamlet of Wakeham on the Isle of Portland, Dorset. The dwelling has two bedrooms consisting of a double and a twin,...

  • From £394
Read more

Little Lodge - Wakeham

Little Lodge is a charming semi-detached property resting in the Pennsylvania Castle Estate on the Isle of Portland. Hosting one double bedroom, along with a bathroom, this property can sleep...

  • From £467
Read more

Telltales - Fortuneswell

Telltales is a charming, contemporary cottage resting amidst Fortuneswell on the Isle of Portland, Dorset. There are two bedrooms in the property sleeping four guests, made up of a double...

  • From £467
Cosy up by the wood burner in the living room
Read more

Chesil Lookout - Fortuneswell

Situated on a one-way street, the house enjoys panoramic views over Chesil Cove to Clay Ope and Chesil Beach. Reached via a causeway from Weymouth, the Isle of Portland is...

Secure your 2021 Portland holiday cottage with just a 33.3% deposit when booking 9 weeks or more in advance.
  • From £619
Read more

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....

  • From £496
Read more

Portland View - Portland Bill

Portland View is a two-bedroom apartment located on the Isle of Portland with sea views from the balcony and perfect for those that love walking and the outdoors. With everything...

  • From £450
Read more

Castle View - Castletown

Castle View is an end-terrace property resting within Castletown, Portland. It houses two bedrooms, comprising of a double bedroom and a twin bedroom, each using the family bathroom with a...

  • From £408
Exterior | Jurassica House, Portland
Read more

Jurassica House - Fortuneswell

Jurassica House is part of our Olympic legacy, home to the Swedish sailing team during the sailing events in 2012. A great location for water sports enthusiasts, walkers, cyclists, rock...

  • From £848
Read more

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....

  • From £381
Read more

The Old Council Chamber - Fortuneswell

The Old Council Chamber is a delightful second-floor apartment lying in the village of Fortuneswell on the Isle of Portland in Dorset. Hosting one king-size bedroom along with a shower...

  • From £328
Read more

The Old Portland Courthouse - Fortuneswell

The Old Portland Courthouse is a Grade II listed converted house situated in Fortuneswell, Portland in Dorset with antique furnishings and sea views. The house can sleep 8 people in...

  • From £944

Sign In