Rent Luxury Holiday Cottages in Isle of Portland

Fortune's Well

• 6 guests

• 3 bedrooms

England, United Kingdom

Escape to the stunning Jurassic Coast and stay at this coastal retreat. It’s just along the shore in Castletown on the Portland peninsula, making this an excellent choice for a seaside getaway – you’ll be close to Chesil Beach and Weymouth.

Sweet Like Taffy

• 6 guests

• 3 bedrooms

Weymouth, Dorset

Step through this cottage's pink front door and you'll find breezy living spaces bathed in light and more than enough room for the whole family to spread out. The pared-back design has some subtle coastal influence – no surprise, given the proximity to Weymouth Harbour – and features like traditional ornamental fireplaces and vintage furniture add just a touch of character.

Cottage Greens

• 6 guests

• 3 bedrooms

Weymouth, Dorset

Offering a tranquil escape on the Jurassic Coast, this charming cottage is perfect for a family. It’s less than a five-minute walk from the sandy beach at Castle Cove and the Rodwell Trail.