Holiday houses in Woolland

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Top-rated holiday rentals in Woolland

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Top Guest favourite

The exterior of Oak Tree Barn displays rustic brick walls complemented by wooden window frames. A small tree is planted in a pot near the entrance, while a bench sits on a gravel path, surrounded by a tranquil rural landscape.

Cottage in Dorset

Lovely cosy place to stay in the heart of Dorset

Oak Tree Barn is a self-catering holiday accommodation in the heart of the village of Hazelbury Bryan, Dorset. The conversion was completed in early 2012 using locally reclaimed materials and keeping many of the original features. The Barn is warm and cosy in winter and cool in summer, the detached Barn has a large open-plan lounge and kitchen with views towards the local hills. The two bedrooms (one double with bath, one twin with shower) overlook paddocks where sheep graze and chicken forage.

LocationValueCheck-in

4.99 out of 5 average rating, 277 reviews

Guest favourite

Home in Winterborne Houghton

Dorset Country Home- 6 Bed - Hot Tub

Spacious dog-friendly 6-bed home in Winterborne Houghton with two en-suites, main family bathroom and a downstairs wet room. Enjoy an open-plan kitchen/dining/living area plus a separate lounge/cinema room. Set in nearly an acre with swings for children, a hot tub, and stunning Winterborne Valley views from every window. Incredible walks start right from the drive, with Milton Abbas, Blandford Forum, and the Jurassic Coast nearby — the perfect countryside escape for families, friends, and dogs.

ValueFamilyView

4.94 out of 5 average rating, 31 reviews

Superhost

A charming barn exterior is featured, surrounded by greenery and blooming white flowers. A shaded outdoor dining area with a round table and chairs is visible on a pebble pathway, offering a serene and inviting space for outdoor relaxation.

Holiday home in Dorset

Cheerful cosy rustic retreat

The Barn at Ridouts is beautifully converted 2 bedroom barn in the Dorset National Park, the heart of Hardy Country. It is peaceful and surrounded by wildlife - comfortable, spacious, light and airy - you can enjoy the log-burner and underfloor heating. Listen to the owls and enjoy starry skies. It is a perfect base for putting your feet up and relaxing, or for getting out walking, cycling and exploring . Find fascinating old towns, pretty villages, great pubs, local shops and places to visit.

FamilyValueAccuracy

4.67 out of 5 average rating, 70 reviews

Top Guest favourite

The exterior of the barn features a wooden facade with large glass doors leading to a private outdoor space. A gravel patio is bordered by wooden seating and surrounded by farmland. Overcast skies add a tranquil ambiance to the scene.

Home in Dorset

The Barn @ Star Farm

Set in the heart of the Blackmore Vale in rural North Dorset, The Barn@Star Farm is a spacious 2 bedroom self catering holiday let furnished and equipped to a high standard. Recently converted the barn has its own private track and has wonderful views over unspoilt farmland. The property is quietly on the outskirts of the village of Hazelbury Bryan and is within a 45 minute drive to the Dorset Coast. The market towns of Sherborne, Blandford Forum and Dorchester are all within 20 minutes drive.

ValueLocationSleep quality

4.96 out of 5 average rating, 338 reviews

Guest favourite

A historic thatched cottage is surrounded by a vibrant display of white daisies in the foreground. Windows with simple curtains are visible, and the thatched roof creates a charming rural appearance. The building features soft curved lines, contributing to the overall appeal.

Cottage in Winterborne Stickland

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

LocationValueHeating

4.92 out of 5 average rating, 126 reviews

Guest favourite

A charming brick and flint cottage stands under a clear blue sky. Symmetrical gabled roofs and evenly spaced windows enhance its facade. Lush greenery from nearby plants adds to the welcoming approach. A pathway leads to a wooden front door, inviting guests into a serene retreat.

Home in Child Okeford

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

LocationFamilyTV

4.99 out of 5 average rating, 148 reviews

Top Guest favourite

A charming Georgian house presents a whitewashed façade, featuring large windows and a wide blue front door. The building is flanked by brick walls and mature greenery, creating a welcoming entrance on a quiet lane.

Townhouse in Blandford Forum

Old Red Lion House in Market Town

A beautiful listed building located on a quiet lane in the centre of the pretty market town of Blandford Forum, offering the perfect place to explore Dorset or simply relax in one of the cosy sitting rooms and indulge in one of the house's many books. Plenty of board games and DVDs will keep the younger ones entertained or get outside to the nearby River Stour to spot otters and kingfishers (just a 5 minute walk from the house) or head in any direction to Dorset's spectacular countryside.

FamilyLocationAccuracy

4.96 out of 5 average rating, 186 reviews

Top Guest favourite

A cozy living area features a large window offering views of the serene outdoor landscape. A wood-burning stove stands against a brick wall, providing warmth. A rounded coffee table complements the soft seating arrangement, styled with cushions and throws for comfort.

Guesthouse in Child Okeford

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.

FamilyValueKitchen

4.98 out of 5 average rating, 140 reviews

Top Guest favourite

Barn in Woolland

Mount Pleasant Barn in Woolland, North Dorset

🏡 Mount Pleasant Barn | Beautiful conversion with Hot Tub Situated within the triangle of the Dorset towns of Sherborne, Shaftesbury and Dorchester and within easy reach of the Jurassic Coast - stay at this state of the art conversion with uninterrupted views, a wood-fired hot tub and dog-friendly walks on the doorstep. Lovingly restored by the Miller family, this stylish barn with modern comforts, is ideal for families or friends looking for peace, privacy, and a taste of Dorset life.

LocationFamilyBarbecue

5.0 out of 5 average rating, 31 reviews

Guest favourite

A Scandinavian-style cabin nestled within a lush, green woodland. Tall Douglas firs frame the property, contrasting against the clear blue sky. The path leading to the cabin is surrounded by vibrant grass and dense trees, enhancing the secluded and tranquil setting.

Cabin in Milton Abbas

Woodland Cabin with Brand New Sauna

In the heart of ancient Dorset woodland, the Cabin enjoys forest views from every room, a log burning stove, al fresco terrace dining, outdoor showering, sauna, hammock and private wildlife garden. 40 minutes away from the World Heritage Jurassic coast, a perfect destination for nature lovers, walkers and cyclists, this countryside hideaway is perfect for those in need of a digital detox. Unfortunately, it isn’t suitable for children under 5 or large/active dogs (see House Rules).

LocationFamilyHeating

4.94 out of 5 average rating, 150 reviews

Top Guest favourite

Home in West Orchard

Luxurious & rustic renovated Dorset Coach House

The perfect location to get away from it all! Relax in this spacious and self-contained coach house in the North Dorset countryside, stylishly furnished and decorated with a rustic luxe feel, and featuring a sizeable garden for children to play freely. Conveniently located, an ideal springboard for exploring this beautiful corner of England. Cook in the fully stocked kitchen, and dine in the generous living space or on the outside terrace overlooking rolling fields

ValueLocationLayout

4.97 out of 5 average rating, 111 reviews

Guest favourite

The exterior of The Parlour cottage is depicted, featuring a brick façade with large windows that allow natural light to fill the interior. A spacious gravel area surrounds the cottage, providing convenient access. The tranquil countryside can be glimpsed in the background under a clear blue sky.

Cottage in Duntish

The Parlour, Duntish Mill Farm, EV Charging

The Parlour is a 3 double bedroom cottage which is part of Duntish Mill Farm that has recently been lovingly renovated. There is open plan living with vaulted ceilings and a cosy log burner. French doors that lead onto a large private patio area. Located in an AONB of Dorset, we are surrounded by plenty of stunning countryside centrally located between the historic towns of Sherbourne and Dorchester, which is also only a short drive away from the Jurassic Coast.

LocationFamilyBathroom

4.94 out of 5 average rating, 197 reviews