Special Offer Cottages

Portland self-catering accommodation with offers, discounts or deals

New Cottages

New cottages that have been recently added to Portland Holiday Cottages

Pet Friendly Cottages

We have 15 Portland pet friendly cottages to choose from.

Swimming Pools

Browse 4 Cottages With Pools

Hot Tubs

Luxury holiday cottages with hot tubs

Near the Sea

A refreshing cottage holiday by the sea

Romantic Breaks

Romantic Holiday Cottages for couples

5 Star Luxury Cottage Breaks

Enjoy a luxury stay in one of these 5 star rated cottages.


Large Cottages

Holidaying with a large family or group of friends?

Real fire

Enjoy a break all year round with a real fire

Sea View

Portland Cottages with a sea view

Portland Bill

All our cottages located at Portland Bill

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.