Featured Weymouth Properties
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Trinity Cottage
Weymouth, Dorset
Experience the true character of Dorset when you stay at this exquisite cottage in Weymouth. A charming base with room for four guests, the delightful retreat is situated in an enviable position...
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Sun Beam Weymouth
Weymouth, Dorset
This property is conveniently set in a residential area within easy reach of all that vibrant Weymouth has to offer. This coastal town has a sandy beach backed with shops, cafés and...
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Jurassic Hideaway
Weymouth, Dorset
Less than half a mile from the award-winning beaches of Weymouth sits this picture-postcard holiday cottage with cosy decor and ample space for a family of four. This property is ideal for guests...
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Seascape Weymouth
Weymouth, Dorset
Boasting stunning, panoramic views of Weymouth Bay, this modern semi-detached house is situated in a desirable beach-side location. Only a few hundred metres from Overcombe Beach, a popular...
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Billabong Weymouth
Weymouth, Dorset
Enjoy the many attractions of Weymouth from the comfort of this apartment set within a handsome period building. Sleeping four guests, the two-bedroom retreat sits in a residential area and yet is...
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Honeypot Cottage Weymouth
Weymouth, Dorset
Originally part of a farmhouse, this ancient stone and cob cottage is shielded by trees as it sits back from the main road leading into Weymouth, offering a peaceful location to be enjoyed. Head...
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4 Puddledock Cottages
Weymouth, Dorset
This charming three-bedroom cottage is located on a quiet lane in Sutton Poyntz, with ample space for up to six people. With village amenities on your doorstep, plus a location almost equidistant...
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Sunset Cottage Portland
Portland, Dorset
Take a family holiday on the quirky island of Portland. This property is a Grade II-listed building, which has been lovingly restored and made into a charming cottage. Pack up your family and...
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Chesil Lookout
Portland, Dorset
Situated on a one-way street, the house enjoys panoramic views over Chesil Cove to Clay Ope and Chesil Beach. Reached via a causeway from Weymouth, the Isle of Portland is an unique destination,...
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The Cabin At Cackleberry Farm
Broadway, Dorset
Nestled in the peaceful village of Upwey, this charming property is situated on a smallholding with sheep and chickens, offering guests a tranquil countryside retreat. With a plethora of walking...
View PropertyDiscover Your Perfect Coastal Retreat in Weymouth & Dorset
Explore our handpicked collection of holiday homes across Weymouth, Lyme Regis, Dorchester and Portland, from beachfront apartments overlooking Weymouth Bay to countryside cottages in the Dorset hills. Walk the world-famous Jurassic Coast. Visit historic Lyme Regis harbour. Discover Thomas Hardy's Dorchester. Marvel at Portland Bill lighthouse. Whether you're planning a romantic weekend, family beach holiday or group gathering, find your ideal seaside escape today.
Why choose Weymouth Retreats? We offer competitive pricing on quality properties across prime coastal locations. Our portfolio includes pet-friendly homes, luxury lodges with hot tubs, family-sized cottages near golden sandy beaches, and characterful properties close to Dorset's top attractions. Book direct and access genuine availability across Weymouth's seafront, West Bay's dramatic cliffs, Chesil Beach and charming Dorset villages.
From traditional stone cottages to modern sea view apartments, we match every taste and budget. Fancy fossil hunting along the Jurassic Coast? Want easy access to Weymouth's Victorian pier? Need space for multi-generational holidays? Our properties put you steps from beaches, country pubs and Dorset's coastal paths.
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Special Features
Romantic Lodges
Intimate retreats designed for couples, featuring luxurious amenities and secluded settings for unforgettable romantic getaways.
View Couple HideawaysPet Friendly
Your four-legged family members are welcome here, with secure gardens and thoughtful pet amenities at every property.
Dog-Welcoming BreaksEnclosed Gardens
Private, secure outdoor spaces where families can relax with peace of mind while children and pets play safely.
View Garden PropertiesHot Tub Weymouth Lodges
Unwind in your own private hot tub while taking in breathtaking views of the Lake District's natural beauty.
View All LodgesHoliday Ideas
View allRomantic Coastal Hideaways
Intimate retreats for couples seeking Dorset charm
Unwind in characterful cottages and bijou seafront apartments overlooking Weymouth's Georgian harbour, where candlelit dinners feature fresh Dorset crab and scallops whilst watching spectacular sunsets across Portland Bill and the glittering waters of Weymouth Bay.
Pet-Friendly Coastal Escapes
Tail-wagging adventures along the Jurassic Coast
Bring your four-legged friends to dog-welcome properties featuring enclosed gardens and direct access to sandy beaches at Bowleaze Cove, Overcombe and Greenhill, plus miles of coastal path walks where dogs can explore ancient fossils and dramatic Dorset cliffs.
Family Beach Adventures
Action-packed seaside escapes for all generations
Base yourselves in spacious homes featuring enclosed gardens perfect for children, whilst exploring rock pools at Sandsfoot Castle, discovering fossil-rich beaches near Lyme Regis, building sandcastles on three miles of golden sand, and visiting SEA LIFE Centre and Nothe Fort.
Large Group Gatherings
Spacious properties for celebrations and reunions
Toast special occasions in our largest properties featuring expansive entertaining areas, modern kitchens perfect for group dining, and generous gardens where everyone can gather beneath Dorset skies whilst sampling local wines from Furleigh Estate and fresh seafood from Weymouth's famous harbour.