Special Offer Cottages
Portland self-catering accommodation with offers, discounts or deals

Osprey View - Fortuneswell
This terraced house has an open-plan living space with a kitchen, a dining area for four guests, and a sitting area with a TV with Freeview. Amenities include an electric...
- 4 2 1 0
- More Details

The Shambles - Fortuneswell
The Shambles is a charming terraced cottage resting in Fortuneswell in Dorset. Hosting two bedrooms, including a double and a twin along with a bathroom, this property can sleep up...
- 4 2 1 0
- More Details

Sea Reach - Chiswell
This townhouse has a first-floor kitchen/diner with an electric oven, gas hob, microwave, fridge/freezer, dishwasher and dining table for six, and a first-floor sitting room with Smart TV. The bedrooms...
- 6 3 2 0
- More Details

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...
- 7 4 4 0
- More Details

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...
- 4 2 1 0
- More Details

Pebbles Reach Fortuneswell - Fortuneswell
The living areas in this terraced, three-storey house include a kitchen/diner with seating for seven, an electric oven and hob, microwave, fridge/freezer and dishwasher, a utility/cloakroom with washing machine, and...
- 7 3 2 1
- More Details

Gone Coastal - Southwell
The living areas in the property consist of an open-plan living area with a kitchen with an oven, hob, microwave, fridge/freezer, washing machine, and a sitting room with a TV....
- 2 1 1 1
- More Details

Apartment 2 Portland - Southwell
This second-floor apartment consists of a studio-style layout with a kitchen with a combi oven/microwave, fridge with icebox, kettle toaster, dining seating for two and a sitting area with sofa...
- 2 1 1 0
- More Details

5 Coastguard Cottage - Fortuneswell
The living areas in the property consist of a kitchen/diner with oven and hob, microwave, fridge, dining seating for two people, a sitting room with TV and a conservatory with...
- 2 1 1 0
- More Details

Kimberlin - Chiswell
The living space includes a kitchen/diner with an electric oven and hob, microwave, fridge/freezer, dishwasher, washing machine, tumble dryer, dining seating for six, while the sitting room has a TV....
- 6 3 2 0
- More Details
New Cottages
New cottages that have been recently added to Portland Holiday Cottages

The Shambles - Fortuneswell
The Shambles is a charming terraced cottage resting in Fortuneswell in Dorset. Hosting two bedrooms, including a double and a twin along with a bathroom, this property can sleep up...
- 4 2 1 0
- More Details

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...
- 7 4 4 0
- More Details

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...
- 4 2 1 0
- More Details

Pebbles Reach Fortuneswell - Fortuneswell
The living areas in this terraced, three-storey house include a kitchen/diner with seating for seven, an electric oven and hob, microwave, fridge/freezer and dishwasher, a utility/cloakroom with washing machine, and...
- 7 3 2 1
- More Details

5 Coastguard Cottage - Fortuneswell
The living areas in the property consist of a kitchen/diner with oven and hob, microwave, fridge, dining seating for two people, a sitting room with TV and a conservatory with...
- 2 1 1 0
- More Details

Kimberlin - Chiswell
The living space includes a kitchen/diner with an electric oven and hob, microwave, fridge/freezer, dishwasher, washing machine, tumble dryer, dining seating for six, while the sitting room has a TV....
- 6 3 2 0
- More Details

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...
- 12 6 2 1
- More Details

Spring Rose Cottage - Fortuneswell
Spring Rose Cottage is a superb property resting in Fortuneswell, Dorset. Here, you will find three bedrooms, comprising of a family bedroom with twin beds and a bunk bed, and...
- 8 3 1 1
- More Details

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...
- 6 3 3 2
- More Details

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....
- 4 2 1 2
- More Details
Portland Holiday Cottages
Portland may only be 4 miles long by 2 miles wide but it packs in the attractions and activities like nowhere else in Dorset. Portland has a great mix of sports activities to experience. The windsurfing, sailing and kitesurfing are world-class but also good for beginners. The diving is excellent with many wrecks to explore and there are over 1,000 routes for climbers. There is a rich history to explore from D-Day to a Mesolithic site dating back 8,000 years. For ornithologists, Portland lies on a migration route and has many rare visitors. Walkers will enjoy the many routes almost always accompanied by stunning sea views. There is even a sculpture park with pieces from leading artists and local talent.
There is a good mix of holiday cottages on Portland. We have quaint fisherman’s cottages made from Portland stone. Or new apartments with views over Portland Harbour. With 39 cottages, we have one of the biggest choices of Portland self-catering accommodation.