Self Catering Holiday Cottages in Dorchester

This popular cottage is on a quiet road in the peaceful hamlet of Chaldon Herring, within walking distance of the village pub and the coastal footpath that leads to Durdle Door and Lulworth Cove, part of the Jurassic coast. Dorchester, Weymouth and Moreton area are all within a short drive, as are favourite Dorset attractions such as the Bovington Tank Museum and Monkey World. The Jurassic Coast makes an excellent holiday destination at any time of the year and this comfortable cottage, which sleeps up to six people in three bedrooms, is the perfect base for couples, families and friends from which to explore it.

Picture postcard pretty, Damers is a traditional thatched holiday cottage in the peaceful Dorset village of Chaldon Herring, just inland of the stunning Jurassic Coast. Perfect for a family holiday, this welcoming holiday retreat sleeps up to five guests in three bedrooms and unlike most Dorset cottages is spacious, has a safe staircase for children and older visitors and two bathrooms, though you still have to watch your head in some places. It also has the advantage of off-street parking.  As well as a large garden, there is a playing field opposite the cottage and a country pub a short stroll away with outside seating.  Durdle Door and Lulworth Cove are within easy reach without having to suffer the crowds whilst the many attractions of Dorset, Dorchester's dinosaur museums, Moreton church, Weymouth sands, The Bovington Tank Museum and Monkey World are all within easy reach.

Set back from a quiet country lane in the peaceful village of Chaldon Herring, and only a few minutes walk from the popular Sailor's Return pub, Rex Officio is a charming holiday home designed with couples in mind. Previously a store building, it has been transformed into a romantic retreat with a very comfortable open-plan living area and kitchen downstairs, and a spacious bedroom with ensuite upstairs. All of Dorset's favourite attractions are on your doorstep. You can easily reach Durdle Door, Lulworth Cove and the Jurassic Coast footpath, as well as drive to charming towns and villages including Dorchester, Moreton and Weymouth.  Bovington Tank Museum and Monkey World are also nearby, as are many walking and cycling trails to suit all abilities.

Accessed via the rockery and a few steps, Poacher's Cottage is a great choice with families and couples and has its own private sun terrace for relaxing during the warmer months. Ideally positioned just a mile from the gorgeous shingle beach at Ringstead Bay, there are a wealth of attractions for day trips out (Weymouth, Poole and Bournemouth are just a few of the highlights within easy driving distance), and superb walking with the South West Coastal Path easily accessible (a 7-mile walk takes you to Lulworth Cove via Durdle Door). A great base for a seaside break or as a base for enjoying all that Dorset has to offer. Tourist board rating: 4 Star Gold

Foxes Cottage ticks all the boxes for a holiday in Dorset, whether you simply want to relax on a beach, discover the many attractions of the area including its stunning Jurassic Coastline, or lace up your walking boots and explore the South West Coastal Footpath. Just a mile from Ringstead Bay beach, this well presented self-catering retreat is a popular choice with couples. Tourist board rating: 4 Star Gold

The perfect retreat just for two within easy reach of Lulworth Cove and Durdle Door on Dorset's World Heritage Jurassic Coastline. Right in the heart of Purbeck, this stylish holiday home provides all the right ingredients for a relaxing break and a great self-catering base for exploring the areas many attractions.  The RSPB Nature Reserve at Arne, from where the BBC Springwatch is broadcast, is very close by.

Whether you're travelling with your kids, extended family or a group of friends, everyone will love Gould's Farmhouse. Four large bedrooms, three bathrooms and three sitting rooms, together with a spacious country kitchen and fantastic garden mean you can enjoy being together while still having your own space. It's on a quiet lane in Milborne St Andrew, within walking distance of a great pub (The Royal Oak), the village shop and a kids playground, and close to the vibrant market towns of Dorchester and Blandford. The Jurassic Coast, Weymouth and Poole are all a short drive away, and there are beautiful National Trust properties like Hardy's Cottage to enjoy. Footpaths, including the South West Coast Path, bridle ways and cycle paths are plentiful so you can be as active as you like, or simply recline on a lounger in the garden with a good book and enjoy not having to please anyone but yourself. Ideal for those with limited mobility as there is a lift to the upstairs.

Sitting on Dorset's World famous Jurassic Coastline, Gamekeeper's Cottage is an excellent choice for couples wanting to explore the many attractions of this beautiful part of the South West. With superb walking (including a 7 mile each way walk to Lulworth Cove via Durdle Door), an abundance of attractions close by (Weymouth, Bournemouth and Poole to name just a few) and a lovely beach to walk to for relaxing, Gamekeeper's Cottage is perfect for a break away or holiday at any time of the year. Tourist board rating: 4 Star Gold

With a ground floor en-suite bedroom and nursery with cot on the first floor, Pheasants Cottage is a perfect choice for families. Sleeping six guests in comfort and style, this beautifully presented flexible cottage sits in a superb position just a mile from Ringstead beach on Dorset's stunning World Heritage Jurassic Coast. Fabulous walking with the South West Coastal Path easily accessible, an abundance of attractions close by including Lulworth, Durdle Door, Weymouth and Poole, and a beach for lazy days. All the right ingredients for a seaside holiday. Tourist board rating: 4 Star Gold

*************SPRING OFFER************ ******FOR THE MONTH OF MARCH 2026, WE ARE ABLE TO OFFER 50% DISCOUNT ON ALL WEEKLY BOOKINGS****** With just the birds and wildlife as your neighbours, the Trout Barn offers a peaceful and secluded getaway in the rural village of Hermitage on the edge of a Dorset Area of Outstanding Natural Beauty. With two trout and one carp fishing lakes, beautiful countryside walks from the front door and a number of attractions nearby, there is plenty to keep all ages entertained. The modern built accommodation can comfortably sleep eight guests in 3 bedrooms, all with en-suite facilities. The very spacious accommodation is on one level, making it easy access for all ages. The Trout Barn is the perfect self-catering holiday accommodation for families, friends and couples looking for a slice of beautiful rural Dorset, that'll not disappoint. We offer pet friendly accommodation, with a secure garden for your 4 legged friends. Come and enjoy a rural countryside break that so many others have enjoyed.

With a fabulous four-poster double, Owls Roost is a popular choice with couples looking for a luxurious retreat. Perfectly placed just a mile from Ringstead Bay beach on Dorset's world famous Jurassic coastline, guests can enjoy plenty of sea air, attractions including Durdle Door, Lulworth Cove, Poole and Weymouth, as well as miles of coastal footpath to explore. Tourist board rating: 5 Star

"The Haymow , Dorchester " is a 1 bed holiday Cottage sleeping up to 2 guests in Dorset. Recently renovated, The Haymow at Duntish Mill Farm is a wonderful light-filled single-storey property which has been carefully designed and styled to provide comfortable accommodation for a couple. With contemporary furnishings,and attractive...

"The Old School Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in Dorset. Tincleton is a tiny hamlet in Dorset, nestled in a beautiful rural setting within the valley of the River Frome. The hamlet is just five miles east of the county town of Dorchester which has many shops and attractions to discover. The area has...

"Happiness Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in Dorset. The pretty West Dorset village of Piddlehinton can be found in the quaintly named Piddle Valley, an Area of Outstanding Natural Beauty, only 8 miles from Dorchester, situated off the main road on a private track. The village is surrounded by...

"Norden House" is a 3 bed holiday Cottage sleeping up to 6 guests in Dorset. The delightful village of Maiden Newton rests in the heart of Dorset Area of Outstanding Natural Beauty, boasting a wealth of shops, a local pub and restaurant, and the historic church of St. Mary. Nearby rests the picturesque South Dorset...

"Manor Farmhouse, Dorchester" is a 4 bed holiday Cottage sleeping up to 8 guests in Dorset. Manor Farmhouse is beautifully presented, and has period features and a light airy feeling throughout. On the ground floor the front door opens to the entrance hall with, on one side the comfortable sitting room which has an open fireplace and...

"1 Bed Apartment in Dorchester" is a 1 bed holiday Apartment sleeping up to 2 guests in Dorset. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 1 twin bedroom - 1 en-suite shower room and WC - Electric oven and hob, microwave, fridge/freezer and washer/dryer - Night storage heater...

"Crumpet Cottage , Dorchester" is a 2 bed holiday Cottage sleeping up to 4 guests in Dorset. Crumpet Cottage, located in the pretty hamlet of Chebbard, has been lovingly refurbished to create a luxurious and comfortable holiday home, providing the perfect base for your Dorset adventures. Close to the quaint and attractive villages of...

"Willow" is a 2 bed holiday Cottage sleeping up to 4 guests in Dorset. Located in the county of Dorset, Maiden Newton is a town-sized village that is surrounded by an Area of Natural Beauty. Shops, a pub, and a restaurant may all be found in the village. The Church of St. Mary in Maiden Newton is another...

"Sunny Croft" is a 3 bed holiday Cottage sleeping up to 5 guests in Dorset. A trip to the county of Dorset would not be complete without visiting the market town of Dorchester, with its Roman roads, museums and a number of pubs and restaurants. Enjoy a picturesque walk around Maiden Castle or visit the County Museum...

"Church Cottage, Dorchester" is a 2 bed holiday Cottage sleeping up to 4 guests in Dorset. Church Cottage is an attractive, thatched cottage nestling proudly next to the church in this friendly and popular Dorset village with shop and pub. The cottage was constructed in 2013, and has been carefully and beautifully furnished with each...

"3 Bed Cottage in Higher Wraxall" is a 3 bed holiday Cottage sleeping up to 6 guests in Dorset. Additional information and rules. Please enquire if you wish to bring more than 1 dog - Sleeps 5+1 with additional pull-out full-size single bed available on request - 3 bedrooms - 2 doubles and 1 single (with additional single...

"Myrtle Cottage" is a 4 bed holiday Cottage sleeping up to 7 guests in Dorset. We adore this rural, traditional Dorset village with 2 pubs, surrounded by idyllic countryside and just a couple of miles from the stunning Jurassic Coast.. Ground Floor: Open plan living...

"2 Bed Cottage in Dorchester" is a 2 bed holiday Cottage sleeping up to 4 guests in Dorset. Additional information and rulesNo dogs allowed - 2 bedrooms - super-king-size zip-and-links (which can be made into a twin on request) - 1bathroom with bath, separate shower and WC - Electric Range master oven and hob,...

"Sea Views" is a 3 bed holiday Cottage sleeping up to 5 guests in Dorset. Abbotsbury is a historic and charming village lying on the Dorset Jurassic Coast. Home to the delightful Abbotsbury Subtropical Gardens, with a wonderful array of plants leading down to the long-stretching Chesil Beach, as well as Abbotsbury...

"3 Bed Cottage in Dorchester" is a 3 bed holiday Cottage sleeping up to 4 guests in Dorset. Additional information and rulesNo dogs allowed - 3 bedrooms – 1 super-king-size with additional sofa bed (please request this at point of booking) and 2 singles - 2 bathrooms - 1 wet room with shower and WC, 1 en-suite bathroom...

"Farm Cottage, Dorchester " is a 3 bed holiday Cottage sleeping up to 6 guests in Dorset. Recently renovated, Farm Cottage at Duntish Mill Farm is a stunning light-filled single-storey property, which has been designed to provide comfortable accommodation for four adults and two children. With air-conditioning, attractive and...

"3 Bed Cottage in Hilfield" is a 3 bed holiday Cottage sleeping up to 6 guests in Dorset. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 3 Bedrooms – 2 doubles and 1 bunk bedroom - 1 bathroom - shower over bath and WC - Electric oven and hob, microwave, fridge with ice...

"2 Bed Cottage in Dorchester" is a 2 bed holiday Cottage sleeping up to 4 guests in Dorset. Additional information and rulesNo dogs allowed - 2 bedrooms – 1 double and 1 twin - 1 bathroom with bath, handheld shower and WC - Kitchen - electric oven and induction hob, microwave, Nespresso coffee pod machine (pods not...

"5 Bed Cottage in Dorchester" is a 5 bed holiday Cottage sleeping up to 9 guests in Dorset. Additional information and rulesNo dogs allowed - 5 bedrooms – 2 king-size, 1 twin, 1 bunk room, 1 single (ground floor) - Please note: bunk room has restricted headroom, suitable for under 16's - 3 bathrooms - 1 bath with shower...

"4 Bed Cottage in Dorchester" is a 4 bed holiday Cottage sleeping up to 8 guests in Dorset. Additional information and rulesNo dogs allowed - 4 Bedrooms – 1 king-size, 1 twin and 2 super-king-zip-and-links (which can be made into twins on request at the point of booking) - 1 Bathroom with shower over bath and WC, 1...

"5 Bed Cottage in Dorchester" is a 5 bed holiday Cottage sleeping up to 10 guests in Dorset. Additional information and rules. Please enquire if you wish to bring more than 1 dog - Sleeps 10+2 with 2 single beds available in one of the double bedrooms, on request - 5 bedrooms - 1 super-king-size zip-and-link (which...

"Hurdlemakers Hut" is a 1 bed holiday Lodge sleeping up to 2 guests in Dorset. Only eight miles from Dorchester, in the charmingly called Piddle Valley, an Area of Outstanding Natural Beauty, is the charming West Dorset village of Piddletrenthide, which is off the main road on a private track. The community is surrounded...

"Parlour Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in Dorset. Set in stunning surroundings, this cosy traditional holiday cottage has a lot to offer. A fantastic base for exploring Dorset and Somerset for families, friends it really is a true countryside escape.. All on the Ground Floor:...

"Dorset Alpaca Shepherd's Hut" is a 1 bed holiday Cottage sleeping up to 2 guests in Dorset. Overlooking open countryside, this Shepherd’s Hut is the perfect place to relax all year round.. 3 steps to entrance. All on the Ground Floor: Open plan living space. Living area: (No TV),...