Holiday Cottages in Weymouth
Self-Catering Cottages and Exploring Weymouth Like a Local
If you’re searching for holiday cottages near Weymouth, you’ll find plenty to love here. Weymouth blends the relaxed atmosphere of a traditional seaside town with plenty to explore. There’s a long, sandy, award-winning beach with calm, shallow waters, ideal for swimming and families. Nearby, the working harbour has its own charm, shaped by fishing boats, waterside restaurants, pubs, and cafés, all offering views across to the historic Nothe Fort.
Our current collection of cottages sits just outside town, close to Dorchester’s historic streets and surrounding countryside, and offers a comfortable base for exploring both coast and country. From dog‑friendly stays and relaxed family bases to more luxurious countryside homes, each one has been chosen for its comfort, space and location.
Discover Things to See & Do in Dorset
Whether you’re seeking rugged coastal walks, charming market towns, or the freshest seafood the south coast has to offer, our guide to Dorset has everything you need, from the best places to eat and drink, to unmissable attractions and outdoor adventures to make the most of your visit.
Frequently Asked Questions
With calm, shallow waters, it’s perfect for swimming, paddleboarding, and family days by the sea. After a day at the beach, our children always enjoyed an ice cream from Rossi’s — made fresh according to a family recipe that’s been closely guarded since the 1930s. Beyond the main beach, there are quieter spots too, from the secluded Castle Cove Beach to the shingle stretch at Greenhill, and, a little further along, the more untouched, open shoreline at Ringstead Bay.
View our Explore guide for more recommendations on the best beaches to visit in Weymouth.
Eating out in Weymouth is part of the enjoyment of staying here. The harbour is full of pubs and restaurants right by the water. We often recommend Catch at the Old Fish Market for something a little more special, Enzo’s Ristorante for classic Italian opposite the beach, and Olivetto for its views across the bay.
Brewer’s Quay, on the far side of the harbour, is another good option. Popular places to visit include The George Bar & Grill, Bennetts Fish and Chips takeaway, and Sticks & Bones, where board games and retro arcade games keep children happily entertained. Just outside town, welcoming country pubs such as The Smuggler’s Inn and The Springhead are some of our favourites.
View our Explore guide for more recommendations for places to eat and drink in Weymouth.
Weymouth is a destination that appeals to all ages and interests. SEALIFE Weymouth is popular with families, featuring underwater tunnels that allow visitors to walk beneath sharks. The town’s history is also easily explored, from harbour walks and the Tudor House Museum to Nothe Fort, a Victorian fort overlooking the harbour that has been restored and is open to visitors. For a more adventurous experience, boat trips and exhilarating RIB rides depart from the harbour, offering a memorable way to explore the Jurassic Coast.
Explore our things to do guide.
Weymouth is perfectly positioned for exploring some of Dorset’s most distinctive landscapes and landmarks. Portland Bill is located at the tip of the island, and watching the sea crash against the rocks makes it a memorable place to visit at any time of year. Nearby, Chesil Beach extends for miles along the coast, offering a striking contrast to the sandy beaches around Weymouth. To the east, Durdle Door is one of Dorset’s most recognisable sights, best visited early or late in the day. Inland, the historic streets of Dorchester run alongside rolling countryside, with landmarks such as the Cerne Abbas Giant.