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Popular Cottages
- Northern Byre
- Stone House
- Lightkeepers Cottage
- Sunshine Cottage West Bexington
- Idle Hours Worth
- Braeside
- Weymouth Bay Apartment C
- Agua de Plata
- Sea Gem
- Big Oak View
- The Old Barn
- Sea View Villa
- Piddle Inn
- All Views
- Waltham House
- Speedwell Cottage
- Old Orchard Melbury Osmond
- The White Cottage
- Hillside Cottage
- The Stable House
- Court Close
- The White House
- Fieldfare
- Bay Tree Cottage
- Hamilton House
- The Old Forge West Lulworth
- Brook House
- Purbeck View Kingston
- Harbourside House
- Lower Farm
Osmington Holiday Cottages
Our curated collection of Osmington cottages has something for everyone... Whether you're idea of a great holiday is a modern glamping pod, or a rustic thatched cottage that's a hundred years old, we've got you covered! Each of our rentals features a private hot tub and everything you need for your next family holiday, romantic retreat or that getaway with a group of friends. Discover find your perfect Osmington holiday home today.
- Grade II-listed thatched cottage
- Sleeps eight across four bedrooms
- Enclosed garden with summer house
- Traditional AGA in equipped kitchen
- Two miles from coastal paths
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Visitor Rating
4.8
- Indoor swimming pool facility
- Games room with entertainment
- Five en-suite bedrooms available
- Enclosed garden with BBQ
- Near Jurassic Coast beaches
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Visitor Rating
4.2
- Pool table for group fun
- Stunning sea and countryside views
- Two minutes from Smugglers Inn
- Large garden with fruit trees
- Direct coastal path access
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Visitor Rating
4.8
- Four bedrooms sleeping seven
- Enclosed garden with patio
- Off-road parking two cars
- Walking distance Bowleaze Cove
- Fully-fitted kitchen facilities
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Visitor Rating
4.8
- Sleeps 8 guests comfortably
- Four well-appointed bedrooms
- Open-plan social living space
- Private enclosed garden area
- Near Jurassic Coast attractions
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Visitor Rating
4
- Sleeps 10 with games room
- Four en-suite bedrooms available
- Large enclosed garden for dogs
- Four miles from Lulworth Cove
- Three car parking spaces included
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Visitor Rating
4.9
- Stunning sea views to Portland
- Sleeps 7 in 3 bedrooms
- Garage parking space included
- 2 minutes walk to beach
- Dog-friendly with secure garden
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Visitor Rating
4.9
- Stunning sea views from bedrooms
- Just 2 minutes to beach
- Sleeps 7 across 3 bedrooms
- Secure garage parking space
- Shared garden for groups
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Visitor Rating
4.5
- Sleeps 12 across six bedrooms
- Multi-level garden with play area
- Near Weymouth beach and attractions
- Jacuzzi bath and spacious interiors
- Off-road parking for two cars
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Visitor Rating
4.3
- Sleeps 15 across seven bedrooms
- Six bathrooms prevent morning queues
- Kitchen table seats 14 people
- Ground floor bedroom and facilities
- Blue Flag beach 0.3 miles
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Visitor Rating
4.9
- Direct seafront location
- Multiple group bedrooms
- Spacious living areas
- Georgian period features
- Walking distance harbour
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Visitor Rating
5
- Six themed bedrooms sleeping twelve
- Games room with Xbox entertainment
- Enclosed garden with astro turf
- Just 0.1 miles from beach
- Walking distance to major attractions
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Visitor Rating
4.8
- Sleeps 12 across six bedrooms
- Seven bathrooms including ensuites
- Five minutes walk to beach
- Contemporary kitchen with high-spec appliances
- Ground floor bedroom for accessibility
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Visitor Rating
4.8
- Sleeps nine across four bedrooms
- Three bathrooms including ground floor
- Enclosed garden with patio furniture
- Off-road parking for two cars
- Walking distance to Weymouth Beach
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Visitor Rating
4
- Five bedrooms sleeping nine
- Beach just 0.3 miles away
- Enclosed garden with patio
- Pet friendly for dogs
- Central Weymouth location
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- Victorian elegance sleeps 8
- Kitchen with Aga dining 9
- Parking for 4 cars
- Play area with toys
- Rural estate location
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- Victorian elegance with modern comfort
- Four bedrooms sleeping eight guests
- Large courtyard with BBQ facilities
- Parking for four cars included
- Two miles from historic Dorchester
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- Two Palladian houses sleeping 19
- 8 bedrooms with 6 bathrooms
- Jurassic Coast 10 minutes drive
- Lift access and play area
- Came Estate countryside location
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Visitor Rating
4.5
- Sleeps 9 across 4 bedrooms
- 3 minutes walk to beach
- HD TVs in every bedroom
- Enclosed garden with storage
- Two car parking permits
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Visitor Rating
4.9
- Lakeside home with private jetty
- Swimming pool and gym access
- Sleeps 8 in four bedrooms
- Open-plan living for groups
- Peaceful Dorset estate location
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Visitor Rating
3.9
- Spacious group lodge accommodation
- Multiple vehicle parking spaces available
- Minutes from Weymouth sandy beaches
- Open plan living areas
- Close to Portland Bill Lighthouse
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Visitor Rating
3.7
- Direct beachfront Georgian house
- Five en-suite bedrooms available
- Spectacular sea views throughout
- Sleeps ten guests comfortably
- Prime Weymouth seafront location
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- Beachfront location with sea views
- Sleeps 8 adults in 3 bedrooms
- Three bathrooms including two en-suites
- Walking distance to bars and restaurants
- Large Smart TV and games room
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Visitor Rating
5
- Sleeps 13 across six bedrooms
- 30 seconds from Weymouth beach
- Games room with arcade machine
- Off-road parking for two cars
- Six bathrooms prevent morning queues
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Visitor Rating
4.5
- Seafront location with sea views
- Five bedrooms sleeping ten guests
- Two cosy woodburning stoves
- Pet-friendly for two dogs
- Walking distance to attractions
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Visitor Rating
4.7
- Minutes from beach and harbour
- Three bedrooms sleeping seven guests
- Open-plan living and dining area
- Recently added en-suite bathroom
- Central Weymouth town centre location
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Visitor Rating
4.4
- Central harbour location
- Steps from beach access
- Sleeps 8 across levels
- Ground floor apartment available
- Pet-friendly for dogs
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Visitor Rating
4.8
- Harbourside location with spectacular views
- Three en-suite bedrooms sleep eight
- Open-plan living space for groups
- Steps from Weymouth attractions
- Immaculately clean and well-equipped
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Visitor Rating
4.6
- Spacious group accommodation
- Multiple bedrooms available
- Large social areas
- Beautiful Dorset countryside
- Near famous coastal attractions
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Explore more of Dorset
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Abbotsbury Arne Askerswell Beaminster Bere Regis Blandford Forum Bournemouth Bridport Burton Bradstock Cerne Abbas Charmouth Chetnole Chideock Christchurch Corfe Castle Crossways Dewlish Dorchester East Chaldon Eype Farnham Fleet Hengistbury Head Hilton Holwell Kimmeridge Langton Herring Langton Matravers Lilliput Lyme Regis Maiden Newton Mapperton Milton Abbas Mudeford Netherbury Northport Nottington Osmington Overcombe Piddletrenthide Poole Powerstock Purbeck Sandbanks Seatown Shaftesbury Sherborne Shipton Gorge Southwell Studland Sturminster Newton Swanage Symondsbury Tolpuddle Trent Upwey Wareham West Bay West Lulworth Weymouth Whitchurch Canonicorum Wootton Fitzpaine Worth Matravers Wyke Regis