Vacation rentals in Winterborne Stickland

Cute cob cottage - own garden

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. The perfect bolt hole to explore Dorset from, with the famous Jurassic coast only 45 minutes away. We also have a pool available on our other listing.

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

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

Cosy Countryside 2-Bedroom Guest House

Escape to our cosy countryside annexe in Child Okeford within walking distance to historic Hambledon Hill. Set beside a peaceful stream with woodland views and birdsong, it’s perfect for a rural getaway. The self-contained space has 2 bedrooms (one with cot), a fully equipped kitchen for home cooking, and a shower room with washer and dryer. Enjoy the wood fire, private deck with grill, village shop and pubs. A peaceful home away from home to unwind and explore the charm of rural Dorset.

Quiet Comfort in the Countryside

Damson Cottage is a private, detached holiday retreat offering beautiful countryside views. With three spacious bedrooms, it comfortably sleeps five. The chef's kitchen provides an ideal space for entertaining. Enjoy the large garden and the tranquillity of this ideal escape. Being located in the heart of Dorset and surrounded by ancient history the cottage is ideally placed for country walks. The cottage is also located near a wide range of golf courses all within a twenty mile radius.

The Covey - 1 Bedroom Annex with Country Views

Situated in beautiful Wessex this self-contained annex located on the outskirts of Blandford is within walking distance of amenities but retains a countryside feel overlooking fields. With one bedroom and separate living area it’s perfect for singles or couples A walk thru video of the property is available on YouTube on searching for TheCoveyBlandford Nearest pub - 10 mins walk Driving mins Nearest shop - Lidl 3 Blandford centre - 5 Poole & Bournemouth / beaches 30-40 Purbecks -40

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.

The Manor House Suite

The Manor Suite is a newly renovated, self-contained retreat in the heart of Milborne St Andrew, a quiet Dorset village. The suite sits in the shadow of a 13th century church, offering a truly peaceful base to explore the region. The Jurassic Coast, Weymouth and Dorchester are all within easy reach. The village is wonderfully quiet and unhurried, with The Royal Oak pub just a short stroll away and Langham's Vineyard nearby for wine tastings and dining.

Luxury Coastal Bolthole · Hot Tub · Beach Access

Walk past what looks like a garage and discover a stunning coastal bolthole all your own. Perfectly formed for two, with uninterrupted sea views, an open-plan living space opening onto a sun terrace, and your own private steps down to Castle Cove beach. Soak in the hot tub, fire up the BBQ, and watch the boats drift by. All towels, toiletries, and even beach kit provided. A romantic, characterful hideaway on the Dorset coast.

No.3

No.3 is a self-contained property which was the extension of the original farm cottage built in 1907, now part of the hosts’ residence (number 4). It has it’s own separate access off a quiet unclassified road leading out of the village of Winterborne Whitechurch with off-road parking. The property has been adapted to provide all the comforts for a quiet enjoyable stay but public transport is infrequent so a car is recommended.