Holiday Cottages in Weymouth, Dorset
Holiday Cottages in Weymouth for Relaxing Dorset Escapes
Looking for holiday cottages in Weymouth? It’s easy to see why this much-loved seaside town has remained one of Dorset’s most popular holiday destinations for generations. From its award-winning golden beach and picturesque harbour to its colourful fishing boats, independent restaurants and easy access to the Jurassic Coast, Weymouth offers the ideal base for exploring the very best of Dorset.
Perhaps it’s an early-morning stroll along the Esplanade before the beach comes alive, watching fishing boats unload the day’s catch in the harbour, or simply enjoying fish and chips by the sea as the evening sun begins to set over Weymouth Bay.
As locals, we keep returning to Weymouth throughout the year. Whether we’re walking through Nothe Gardens with Smarty, meeting family for lunch with a view of the harbour, or exploring the coastline towards Portland and Ringstead Bay, each visit reminds us why it’s one of our favourite places in Dorset.
Our carefully selected collection of holiday cottages in and around Weymouth lets you experience everything this special corner of Dorset has to offer. Some guests prefer to stay close to the coast, while others enjoy returning each evening to the peace and tranquillity of the surrounding countryside after a busy day by the sea.
Whether you’re planning a family beach holiday, a romantic coastal break, a luxury Dorset escape, or a dog-friendly adventure along the Jurassic Coast, you’ll find the ideal base for exploring Weymouth and beyond..
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.
Weymouth Beach and the Beautiful Beaches Nearby
Weymouth Beach is undoubtedly one of the finest family beaches in the UK. Its gently sloping golden sands and calm, sheltered waters have made it a favourite with generations of visitors, and it’s easy to see why. Whether you’re building sandcastles, swimming, hiring a paddle board, or simply relaxing with an ice cream from Rossi’s, it perfectly captures the charm of a traditional British seaside holiday.
And there are so many other beaches within easy reach, too. A walk takes you to Greenhill and Overcombe Beach or in just a short drive you can visit Castle Cove, Sandsfoot Beach, Bowleaze Cove, Ringstead Bay and the spectacular coastline around Chesil Beach. Each offers something different, from family-friendly swimming and watersports to peaceful coves and dramatic Jurassic Coast scenery.
To help explore Weymouth’s beaches, we’ve put together a detailed guide, including local tips and recommendations to help you choose the perfect spot.
Discover Weymouth’s Harbour Food Scene
One of the things we love most about Weymouth is the wide choice of places to eat. And for a harbour of its size, the quality and variety of independent restaurants are genuinely impressive. Whether you’re looking for freshly landed seafood with water views, authentic Italian cooking, a traditional Dorset pub, or simply some of the best fish and chips on the south coast, Weymouth Harbour has quietly become one of Dorset’s best places to dine.
We’ve celebrated family birthdays at Catch at the Old Fish Market, the only restaurant in Weymouth featured in the Michelin Guide. Enjoyed homemade pasta and cocktails at Bonita, tucked into fish and chips from the much-loved Bennett’s Fish & Chips while watching the fishing boats come and go. And discovered newer favourites such as Rice & Sail, which has quickly earned an excellent reputation among locals and visitors alike.
Of course, there’s plenty more to discover. So we’ve put together a dedicated guide featuring Weymouth Harbour’s restaurants, cafés and pubs we genuinely return to, along with local recommendations, hidden gems and our favourite places for everything from brunch and seafood to special occasions.
Explore the Best of Weymouth and Beyond
One of the things we love most about Weymouth is just how much there is to discover beyond its famous beach. Venture a little further and you’ll uncover another side to this beautiful part of Dorset.
Spend the morning exploring the historic harbour before climbing the ramparts of Nothe Fort for spectacular views across Weymouth Bay. Wander through Nothe Gardens, enjoy fresh seafood overlooking the marina or take to the water on a harbour cruise or exhilarating RIB ride along the Jurassic Coast.
Just beyond the town, Dorset opens up in every direction. Head west to the Isle of Portland, where dramatic cliffs, Portland Bill Lighthouse and the sweeping expanse of Chesil Beach offer some of the county’s most memorable coastal scenery. Travel east and you’ll discover Ringstead Bay, Lulworth Cove and the iconic limestone arch of Durdle Door. While inland you’ll find the county town of Dorchester, with picturesque villages and miles of rolling countryside just waiting to be explored.
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 Weymouth 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.
Popular places to visit in the Harbour include The Ship Inn, 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, in Osmington and The Springhead, Sutton Poyntz, are some of our favourites.
View our Explore guide for more recommendations for places to eat and drink in Weymouth. Or read our guide on the best places to eat in Weymouth Harbour.
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.
Yes. Many of our holiday cottages welcome dogs, making it easy for the whole family to enjoy a holiday in Dorset together.
We’ve explored many of the local walks with our dog, Smarty, including Nothe Gardens, Ringstead Bay, Sutton Poyntz and sections of the South West Coast Path. They’re all places we’d happily recommend to guests bringing their four-legged companions.