Winter Short Breaks in Dorset

A fantastic three-bedroom house resting in Swanage, Dorset. Dog-friendly. Off-road parking. Near a beach. Close to amenities. Wareham 10.1 miles; Poole 20 miles.

Beautiful and spacious cottage over three floors in Weymouth. Next to the Old Harbour and close to town centre. Beach 1 mile. Pub and shop 5 min. Beach 1 mile. Dorchester 8.5 miles.

5 Red Sails, a beautifully-presented home in the stunning neighbourhood of Sandbanks in Poole, Dorset. Three-storey house. Terrace with barbecue. Close to beach. Poole 5.2 miles; Bournemouth 6.6 miles.

The BoBo House is a delightful terraced holiday home resting in the popular coastal town of Weymouth in Dorset set over four floors and near the beach. Dorchester 7 miles; Bridport 17 miles.

A period conversion apartment Bayview Loft is located in an upmarket development in a highly desirable area of Weymouth in Dorset. Renovated early 2023. WiFi.

Coastal Charm is a lovely first-floor apartment settled into the seaside town of Swanage, Dorset, with a balcony, and close by shops, pubs, and beaches. Wareham 10 miles; Bournemouth 12.9 miles; Poole 19.9 miles.

Perfectly located on the harbour side in the heart of Weymouth. Watch the boats sail by and the daily catch being landed.

6 Red Sails is a magnificent townhouse in Sandbanks, Dorset, with open-plan living, a balcony with garden views and is close to the beach. Poole 5.4 miles; Bournemouth 5.9 miles.

30 Fleet Street is a lovely, pet-friendly two bedroom cottage located in the delightful town of Beaminster, Dorset and can sleep up to 5 guests. Bridport 6.4 miles; Crewkerne 7.6 miles; Lyme Regis 15.5 miles.

A charming Victorian dwelling resting in the town of Wareham, Dorset. Period features. Woodburning stove. Central location. West Lulworth 8.7 miles; Dorchester 18.5 miles; Weymouth 19.7 miles.

Plain Sailing, a gorgeous holiday home located in the heart of the marvellous seaside town of Weymouth, Dorset. En-suite master. Lake view. Pet-friendly. Dorchester 7.8 miles; Bridport 18.6 miles.

Mackerel Cottage is a beautifully-designed, terrace cottage resting in the heart of Weymouth, Dorset. Woodburning stove. Pet-friendly. Near shop and pub. Dorchester 8.4 miles; Bridport 18.9 miles.

Magnolia cottage is situated in Osmington. Pretty, thatched and very well-equipped. High chair and cot. Wifi. Parking for two cars. Pub 5 min. Weymouth 4.5 miles.

Flat 4 is a second floor duplex apartment resting in the city of Bournemouth in Dorset. Romantic. Near to beach. Enclosed decking. Open-plan. Christchurch 5.7 miles; Poole 6 miles; New Forest National Park 13.7 miles.

A well-appointed, first-floor apartment resting in Weymouth, Dorset. Sea glimpses. Close to amenities, attractions and beach. Stylish. Off-road parking. Open-plan living. Near AONB. Dorchester 8.6 miles; Bridport 18.6 miles.

Sleeps 10, large open plan living kitchen dining room. 3 bathrooms, central Swanage location close to the beach. WiFi.

Glamping cabin on the Jurassic Coast with breakfast is a simple, pet-friendly cabin near Swanage, Dorset, with studio layout, garden views and barbecue. Studland 3.7 miles, Poole, 18.7 miles, Bournemouth 24.3 miles.

93 Abbotsbury Road is a bright pet-friendly house resting in Weymouth, Dorset, boasting an enclosed garden and proximity to local amenities and the beach. Dorchester 8.1 miles; Bridport 17.8 miles.

A well-presented, modern apartment on the rugged Isle of Portland. Far reaching sea views. Open plan living. Balcony with seating. Access to indoor swimming pool and gym. Close to pub, beach and shop. WIFI and allocated parking. Weymouth within 6 miles.

A fabulous, three-storey home resting near Weymouth's Old Harbour in Dorset. Close to amenities, beach and attractions. Near AONB. Open-plan living. Stylish. Dorchester 8.8 miles; West Lulworth 15.8 miles.