Vacation rentals in Winterborne Stickland

The Coach House, Duntish Mill Farm, EV Charging

Whether you're exploring Dorset's countryside and coastline or simply looking to switch off for a few days The Coach House offers a peaceful escape for two. Beautifully renovated it combines exposed beams, a cosy wood-burning stove and a luxurious walk-in rainfall shower with plenty of space to relax and unwind Set within Duntish Mill Farm between Sherborne and Dorchester and within easy reach of the Jurassic Coast, it's the perfect base for discovering some of Dorset's most beautiful landscapes

Ranmoor Estate - Hunters Cottage - Hot Tub & A/C

Welcome to Hunters Cottage – our most opulent luxury cottage at Ranmoor Estate, where refined comfort meets timeless countryside charm. This stunning, air-conditioned retreat is perfect for couples seeking a romantic escape. The main bedroom features a king-size bed and a beautiful slipper bath, creating the ultimate space to unwind. Outside, enjoy your private hot tub and BBQ area overlooking the rolling Dorset countryside — the perfect setting for relaxation, romance, and lasting memories.

Pretty thatched, historic Cottage in an ANOB area

The cottage is a lovely grade II, listed, historic, thatched cottage. It's in a conservation area which is also in an Area of Outstanding Natural Beauty. There are lots of great local country walks. It’s also a central base to visit all that Dorset has to offer; from beaches and beauty spots to country towns. The Crown pub is in the centre of the village, only 5 minutes walk away. Our Sports and Social Club has a a bar and play equipment. It is on the left at the north end of the village

Luxurious Shepherd’s Hut with Hot Tub

Get back in touch with nature at this luxury Shepherd’s Hut nestled in a quiet hamlet. Enjoy the large hut’s interior amid thoughtful industrial style decor and modern finishes and embrace outdoor living in your own large outdoor space, surrounded by breathtaking views of the countryside. Relax in the large fire fuelled hot tub, lounge on the deck in front of the fire pit or grab a bean bag and find a quiet spot in your own private paddock. This place offers luxurious comfort indoors and out.

Stylish Barn Conversion

The Barn is a converted property located at the head of the stunning Tarrant valley within the Cranborne Chase Area of Outstanding Natural Beauty. The main living area has dual aspect and bifold doors out onto an enclosed patio, garden and seating area. Two of the bedrooms have internal balconies into the main body of the barn and triple velux roof windows to enjoy the rural views. The third bedroom has bifold doors onto the patio and an en-suite with rainfall snail shower. TV/cinema room.

Hanford Minima

Immaculate newly renovated three-bedroom cottage, (1 super king en suite, 1 king and 1 twin sharing a family bathroom) dating from the 1840s in typical Dorset brick and flint. Nestled at the foot of Hambledon Hill – between Shaftesbury and Blandford – it's only a mile to the excellent village shop and an easy walk over Hambledon hill to The Cricketer's pub for lunch or a pint. Drive to the Jurassic coast (40 mins) to explore Lulworth Cove or visit the gorgeous beach at Studland or Weymouth

Cute cob cottage

Relax in cosy 2 bedroom cottage at the top of the Winterborne valley. Explore Hardys’ country straight from the door onto miles of bridleways and footpaths with far reaching views. Well equipped with books and games, a log burner, and an out door bbq there is something to do whatever the weather. An enclosed private rear garden for sunny days with use of a shared, adjacent pool upon request. The perfect bolt hole to explore Dorset from, with the famous Jurassic coast only 45 minutes away.

Tudor Rose Luxury thatched cottage Dorset.

A boutique and chic thatched cottage for 2 nestled within the beautiful village of Stourpaine in an AONB. Escape to this romantic couples hideaway for the ultimate luxury getaway. Finished and equipped to a high standard including king size bed with designer linens, roll-top bath and separate shower, cosy lounge, separate dining room, fully equipped kitchen and lovely sunny courtyard. Great walks and the superb village pub are just a short stroll away. 1 small dog is welcome to join you!

No1. The Courtyard, Clyffe House

Enjoy a tranquil break in our recently renovated Grade II listed cottage in the heart of Dorset. No.1 The Courtyard is nestled just outside the village of Tincleton and was originally part of the servant’s accommodation to Clyffe House (1842). We are situated 6 miles from Dorchester, and within easy reach of many Dorset attractions; Lulworth Cove, Durdle Door, Corfe Castle, The Purbeck Hills, Kimmeridge, Southwest Coastal Path, Bovington Tank Museum, Monkey World, Weymouth, Swanage.

Cobblers Cottage, Dorset

Relax and unwind in a newly renovated 18th Century cottage, combining period charm with modern convenience and luxury. Sleeping 6+ in three spacious double bedrooms, one en suite on the ground floor. The cottage also boasts a decadent bathroom, open plan kitchen diner, living room with inglenook fireplace, sun room and front & back cottage gardens. Within 20 minutes of Dorset's top attractions, you can combine rural charm with convenience to truly make the most of your trip!

St James Cottage – Luxurious Dorset Escape

St James Cottage is a beautifully restored four-bedroom, four-bathroom retreat set on Milton Abbas' iconic main street. Blending timeless charm with modern luxury, the home features three elegant living areas, a high-end kitchen, and three inviting fireplaces. Recently decorated to an exceptional standard, this spacious cottage offers the perfect countryside escape in one of Dorset’s most picturesque and historic villages — peaceful, idyllic, and full of character.

Stylish 2BR Barn conversion | Sunset Views

Beautifully renovated, spacious 2 bedroom barn conversion on a traditional Dorset farmyard. Ideal for couples, families, and dog-friendly stays. Set in the heart of the Blackmore Vale, The Flower Barn is half way between Sherborne and Shaftesbury, with quick access to A303 (20 mins) Perfect for short breaks, walking holidays, wedding guests, and half terms. Explore Stonehenge, Salisbury Cathedral, and the Jurassic Coast—all within an hour’s drive.