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Popular Cottages
- Waltham House
- The Arched House
- Purbeck View Kingston
- Mermaid House
- Anchor House
- Drackenorth
- Pebbles Reach
- The Old Forge West Lulworth
- Lamperts Dairy
- Gone Fishing
- Thomas Hardys Old School House
- Tillicum
- Home From Home
- Bay Cottage
- Poorton Hill
- Stapleford Farm
- Shore View
- Sea Gem
- Arne at The Studio
- Skylark
- Manor Farm Barn
- Chalross
- The Blue Cottage
- Hove To
- Glyde House
- Brooklands
- Old Post Office Cottage Osmington
- Coombe Street Cottage
- Beach Haven
- Picardy Cottage
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.
- Multiple bedroom group accommodation
- Spacious social living areas
- Dorset countryside location
- Near Weymouth Beach access
- Off-road parking available
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- 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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- 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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- 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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Visitor Rating
4.6
- Sleeps seven guests comfortably
- Four bedrooms two bathrooms
- Enclosed private rear garden
- Off-road parking two cars
- Ten minutes to Weymouth centre
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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
3.8
- Central Weymouth location
- Four bedrooms sleep eight
- Enclosed private courtyard
- Woodburning stove comfort
- Beach just 0.4 miles
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Visitor Rating
4.5
- Sleeps 12 guests comfortably
- Multiple bathrooms for groups
- Ample parking spaces available
- Near Jurassic Coast beaches
- Peaceful Dorset countryside 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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