Winter Short Breaks in Dorset

This charming, one-bedroom holiday home rests in Winterborne Stickland near Blandford Forum, Dorset. Smart TV. Off-road parking. Romantic. Pet-friendly. Thornicombe 5.8 miles; Child Okeford 7.3 miles; Moors Valley Country Park & Forest 21.7 miles.

A warm and restful converted annex in West Bay, Dorset. Off-road parking. Close to the coast. Bridport 1.5 miles; Lyme Regis 10.9 miles.

A beautiful, second-floor apartment overlooking the harbour in Weymouth, Dorset. Romantic. Sea views. Close to beach. Close to local amenities. Dorchester 8.3 miles; Bridport 19.1 miles.

A detached barn conversion set within the village of Long Bredy. Woodburning fire. WiFi. Weymouth 12 miles; Yeovil 20 miles.

A beautifully furnished annexe cottage on the edge of the little hamlet of Hazelbury Bryan in Dorset. Stunning spiral staircase. Open plan. Conservatory. Sherborne 10 miles

A modern studio apartment on the seafront on Weymouth, Dorset. Open-plan living. Sea views. Perfect for couples.

A superb cottage situated in the rural settlement of Farrington in Dorset. Woodburning stove. WiFi. Pizza oven. Shaftesbury 5.6 miles; Blandford Forum 9.5 miles.

The Pebble is a delightful holiday cottage in Melbury Osmond near Yetminster, offering an enclosed garden and private parking. Closworth 2.8 miles; Beer Hackett 4.6 miles; Sherborne 9.3 miles.

Beck House, a welcoming mews house within a secure gated development in the heart of Weymouth, just a short walk from the harbour, beach and amenities. Dorchester 1.3 miles; Bridport 20.3 miles.

Pets welcome. Parking. 5 minute drive to Bridport, perfect couple romantic retreat. Wifi. Coastal views.

The Halt is a delightful, romantic holiday annex situated in the lovely little village of Maiden Newton in Dorset with a studio-style living space. West Bay 12.2 miles; Weymouth 17.2 miles; Lyme Regis 22.7 miles

Chandlers Nook is a romantic ground-floor studio-style apartment in Portland, Dorset, boasting a harbour view, proximity to the beach and local amenities. Weymouth 5.2 miles; Dorchester 12.6 miles; Bournemouth 42.1 miles.

Perfect cottage for 2, close to Swanage, Open plan living area for two people, dog friendly. Excellent location for local coastal walks.

Swanny View is a welcoming caravan featuring open‑plan living, enclosed decking with furniture, EV charging on‑site and easy access to local amenities. Wareham 9.5 miles; Poole 19.4 miles.

Cosy property located in the coastal village of West Bexington. Perfect for couples with pets. Shop 4 miles, pub 10 min. Beach 10 min. Bridport 6.5 miles.

Tane, a welcoming, pet-friendly home in the heart of a sought-after Dorset village, offering proximity to the village pub and scenic walks and footpaths.

An eye-catching stone cottage resting on the outskirts of Shaftesbury, Dorset. Juliet balcony. Open-plan living. Country views. Shaftesbury 2.6 miles; Child Okeford 8.5 miles.

Beautiful thatched terrace cottage in the heart of Corfe Castle, Dorset. Close to Corfe Castle. Garden. Beach 8 miles. Pub and shop 1 min. Swanage 6 miles.

Located in countryside village of Piddlehinton, Way’s Forge is a lovely cosy holiday retreat. Sleeps 3 people. Garden. Welcomes 2 dogs. Shop 2-3 miles. Pub 2 min. Dorchester 6 miles.

A delightful, romantic bolthole in the third-floor in Weymouth, Dorset. Balconies. Romantic. Sea views. Close to beach. Close to local amenities. Dorchester 8.3 miles; Bridport 19.1 miles.