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Portland Holiday Cottages
Our curated collection of Portland 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 Portland holiday home today.
Visitor Rating
4.9
- Four bedrooms sleep seven guests
- Ground floor bedroom with ensuite
- Enclosed courtyard with play area
- Private parking for two cars
- Walking distance to Portland Marina
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Visitor Rating
4.5
- Sleeps eight across four bedrooms
- Sea views from first floor
- Enclosed AstroTurf garden with putting
- Five minutes walk to beach
- Off-road parking for two cars
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Visitor Rating
4.7
- Sleeps 8 guests comfortably
- Beach 5 minutes walk
- Off road parking spaces
- Open plan group living
- Ground floor bedroom access
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Visitor Rating
4.6
- Grade II listed 1904 courthouse
- Sleeps 8 across 4 bedrooms
- Spectacular Chesil Beach views
- Antique dining table seats 12
- Beach just 5 minutes walk
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Visitor Rating
4.9
- Sleeps 15 across seven bedrooms
- Hot tub and sauna facilities
- Medieval hall with oak panelling
- 7000 acre estate with golf
- Japanese pavilion retreat experience
From £5,579 for 7 Nts
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Visitor Rating
4.7
- Georgian mansion sleeps 33
- Hot tub and games room
- 14 bedrooms 14 bathrooms
- Beautiful walled gardens
- Near Stourhead and Longleat
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Visitor Rating
5
- Swimming pool with pool house
- Seven bedrooms sleeping 12 guests
- Games room with entertainment
- Two acres of private grounds
- Parking for 10 cars
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Visitor Rating
4.8
- Outstanding countryside views
- Ground floor accessible bedroom
- Dual kitchen setup
- Spacious rooms throughout
- Beautiful peaceful location
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Visitor Rating
4.9
- Wood-fired hot tub
- Five ensuite bedrooms
- Open-plan group living
- Countryside wildlife views
- Near Shaftesbury attractions
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Visitor Rating
4
- Spacious farmhouse for large groups
- Peaceful fishing ground setting
- Multiple vehicle parking spaces
- Close to Stourhead and Longleat
- Pet friendly Dorset countryside retreat
From £969 for 7 Nts
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Visitor Rating
4.9
- Sleeps 8 in 4 bedrooms
- Private wood-fired hot tub included
- Games barn with table tennis
- Countryside walks from the door
- Near Shaftesbury and Longleat Park
From £1,213 for 7 Nts
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Visitor Rating
4.8
- Hot tub in private courtyard
- Pool table and table tennis
- Sleeps 8 with enclosed garden
- Three bathrooms, well-equipped kitchen
- Near Sherborne, welcomes three dogs
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Visitor Rating
4.9
- Hot tub and games room
- Sleeps 8 with 3 bathrooms
- Six off-road parking spaces
- Welcomes up to three dogs
- Six miles from Sherborne attractions
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Visitor Rating
4.5
- Sleeps 16 across 8 bedrooms
- All bedrooms have en-suites
- Parking for 7 cars
- Museum Inn next door
- Enclosed garden for pets
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Visitor Rating
4.8
- Three separate barn conversion cottages
- Games room with entertainment facilities
- Sleeps 20 across 10 bedrooms
- Parking for 8+ cars included
- Ground floor accessible accommodation
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Visitor Rating
4
- Indoor heated swimming pool access
- Sleeps 8 in 4 bedrooms
- Play area and football pitch
- Two lakes in extensive grounds
- Wood burner and open-plan living
From £899 for 7 Nts
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Visitor Rating
4
- Sleeps 10 in five bedrooms
- Three bathrooms including two en-suites
- Games room with table tennis
- Expansive grounds with resident animals
- Parking for up to eight cars
From £1,592 for 7 Nts
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Visitor Rating
4.9
- Five spacious double bedrooms
- Four bathrooms plus downstairs WC
- Large kitchen with AGA
- Two separate sitting rooms
- Beautiful rural Dorset location
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Visitor Rating
4
- Four en-suite bedrooms sleeping eight
- Open-plan living with vaulted ceiling
- Outdoor kitchen with plancha grills
- Enclosed garden and shared paddock
- Near Bournemouth and New Forest
From £1,265 for 7 Nts
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Visitor Rating
5
- 200-year-old Dorset farmhouse
- Spacious group accommodation
- Near Sherborne town centre
- Sympathetically refurbished throughout
- Beautiful countryside setting
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- Sleeps 16 luxury cottage
- Heated swimming pool available
- Private tennis court included
- Games room entertainment facilities
- One acre private gardens
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- Private hot tub for groups
- Rural Dorset countryside location
- Multiple bedrooms and bathrooms
- Close to coast and attractions
- Spacious open-plan living areas
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Visitor Rating
5
- Hot tub in private garden
- Four bathrooms for eight guests
- Parking for four cars
- Woodburning stove and underfloor heating
- Near historic Sherborne
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Visitor Rating
4
- Sleeps seven across four bedrooms
- Games room with table tennis
- Large enclosed garden for dogs
- Two bathrooms plus ground floor WC
- Six miles from Sherborne attractions
From £666 for 7 Nts
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Visitor Rating
4
- Sleeps 8 in 4 bedrooms
- Parking for 4 cars
- Split-level garden with BBQ
- Pet-friendly welcomes 2 dogs
- Walking distance to village pub
From £979 for 7 Nts
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- Stylish contemporary barn conversion
- Rural West Dorset countryside setting
- Close to Jurassic Coast
- Spacious group social spaces
- Near Mapperton and Bridport
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Visitor Rating
4.4
- Traditional thatched Dorset cottage
- Piddle Valley AONB countryside
- Minutes from Cerne Abbas Giant
- Easy reach of Jurassic Coast
- Quiet rural village setting
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Visitor Rating
4.8
- Grade II listed working water wheel
- Games room with pool and cinema
- Island garden with footbridge access
- Sleeps eight across four bedrooms
- Six miles from Dorset beaches
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Visitor Rating
4.7
- Hot tub and enclosed garden
- Four bedrooms sleep eight guests
- Ground floor bedroom and bathroom
- Dog friendly with secure garden
- Multiple living areas for groups
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- Large group Dorset countryside property
- Spacious communal living and dining
- Wimborne Minster one mile away
- Kingston Lacy three miles away
- Bournemouth Beach 25 minutes drive
From £7,340 for 7 Nts
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Explore more of Dorset
Popular towns and villages in and around Portland
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