Vacation rentals in Woolland

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Top-rated vacation rentals in Woolland

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Top guest favorite

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

4.98 out of 5 average rating, 225 reviews

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.

Guest favorite

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

4.97 out of 5 average rating, 294 reviews

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.

Superhost

The interior features two twin beds with colorful bedding arranged against wooden walls. A dining table is set with two glasses of red wine, a bottle, and a small vase of flowers. A window offers views of the surrounding greenery.

Shepherd’s hut in Dorset

4.89 out of 5 average rating, 190 reviews

Everdene shepherd's hut

Lovely views of the Blackmore Vale (amazing sunsets weather permitting!) Our huts are in a secluded area of the farm. Kingsize bed/twin beds opposite ends with curtains for privacy. Woodburner, hot/cold running water, fridge, hob, microwave, wardrobe. Picnic bench & fire pit outside. Wonderful walks, only 10 minutes on foot to village shop and pub. Great for families. Short walk to luxury wetrooms, w/m, drier. Fishing on farm. Indoor exercise pool payable locally. (Subject to availability)

Top guest favorite

A light-filled living area features a comfortable sofa with decorative cushions, a coffee table, and a dining table in the background. Wooden flooring adds warmth, and a small indoor plant enhances the space. Natural light streams in from an adjacent window, illuminating the cozy atmosphere.

Farm stay in Blandford Forum

4.94 out of 5 average rating, 139 reviews

Self-contained annexe on organic dairy farm

Whether you’re wanting to have a base for a holiday with family, staying for a wedding, or here on business, I would love to have you stay at Lower Farm. The Annexe is situated on a working organic dairy farm, nestled in the most idyllic part of Dorset; perfectly located for beaching, country pubbing or long walks in the rolling countryside that surrounds. The property has a kingsize bed and a sofa bed. I will always do my utmost to cater to your requirements, just pop me a message ☺️

Top guest favorite

The bright sitting area features a gray sofa adorned with decorative cushions. Large skylights fill the space with natural light, while a wooden coffee table and a minimalist media console are visible. Views of greenery can be seen through the windows, enhancing the bright ambiance.

Condo in Hilton, Blandford Forum

4.96 out of 5 average rating, 156 reviews

Stylish self-contained annexe in rural mid Dorset

A thoughtfully designed space for two in glorious, peaceful Dorset countryside. Located on the edge of the lovely village of Hilton, this is a perfect place to hunker down for a few days or to use as a base for exploring all the amazing places that Dorset has to offer, all within easy reach. We are a gentle half hour stroll from Milton Abbey which is set in a magnificent Capability Brown landscape. We are also an easy trip (approximately 20 miles) from the spectacular Jurassic coast.

Guest favorite

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 Blandford Forum

4.93 out of 5 average rating, 128 reviews

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).

Guest favorite

A well-maintained grassy area is framed by a wooden fence, featuring two buildings: a traditional thatched cottage with a bright yellow exterior and a separate annexe with a balcony. Lush greenery provides a peaceful backdrop, and clear skies complete the serene countryside setting.

Guesthouse in King's Stag

4.94 out of 5 average rating, 156 reviews

The Annexe

Peaceful annexe located within the 2 acre grounds of a traditional thatched cottage . Based within a small village in the beautiful North Dorset countryside. The annexe consists of a bright and airy bedroom/ sitting room upstairs and a kitchen diner with small shower room downstairs The sitting room leads onto a large balcony overlooking a large pond and countryside views The town of Dorchester is 15 miles away with access to the Jurassic coast about a 40 minute drive away

Guest favorite

The exterior of a stone cottage is presented, showcasing a blend of natural stone and brick accents. Two sets of windows frame the entrance, which is adorned with potted plants. A clear blue sky with scattered clouds serves as a backdrop.

Apartment in Droop

4.9 out of 5 average rating, 173 reviews

Locketts - self-contained stylish accommodation

Set in the heart of Dorset, we are situated close to the market towns of Sturminster Newton, Blandford Forum, Sherborne and Dorchester. With far reaching picturesque countryside views, it is also no more than forty-five minutes from the Jurassic Coast, famous for stunning beaches along the South West Coast Path. Dorset has a reputation for award-winning pubs and seafood restaurants. We're in a great spot if you want to break your journey to or on your return from Cornwall

Top guest favorite

The exterior of the restored coach house is shown, featuring a charming brick facade and a slate roof with multiple windows. A pebbled driveway leads to the entrance. Lush greenery surrounds the building and fluffy clouds are visible in the blue sky above.

Cottage in Okeford Fitzpaine

4.97 out of 5 average rating, 373 reviews

The Garden House Okeford Fitzpaine Dorset

The Garden House is a restored spacious 2 bedroom former 19th century Coach house, situated in the centre of an attractive rural village in the heart of the rolling North Dorset countryside. Okeford Fitzpaine, near Sturminster Newton is a picturesque, quiet and peaceful Dorset village with a shop /post office and a good local pub. A perfect destination for families, nature lovers, walkers, cyclists and anyone else wishing to escape to beautiful rural Dorset.

Guest favorite

A view from the studio's balcony reveals a spacious wooden deck furnished with two Adirondack chairs and a small side table. The surrounding countryside features lush green fields, distant hills, and a clear blue sky, creating a serene outdoor retreat.

Apartment in Stoke Wake

4.96 out of 5 average rating, 200 reviews

Willow Tree Farm Studio

Welcome to Willow Tree Farm. We have a lovely large private studio with stunning views from its own balcony across the Dorset countryside. Our space is perfect for two adults to escape the rat race and unwind. The studio has a country theme with a comfy Super King Bed, sofa, an indoor table for two, a TV as well as a large en-suite bathroom. Outside you'll find your own private balcony with garden furniture and a BBQ just down the steps below.

Superhost

A contemporary living area is illuminated by natural light, featuring large glass doors that frame scenic views of the surrounding fields. Two gray sofas are arranged around a central coffee table, creating a welcoming space. A wood burner is positioned against a textured stone wall, complementing the modern decor.

Home in Dorset

4.86 out of 5 average rating, 136 reviews

Melbury Lodge, Dorset - hot tub, stunning views

Stylish and contemporary lodge, located in a peaceful position within the pretty Dorset village of Ansty. The beautifully presented lodge is light and spacious throughout with stunning views from the open plan living, dining, kitchen area. Doors open to large decked area for alfresco dining. A cosy wood burner is perfect for the cooler evenings and of course the real highlight is the luxurious hot tub to be enjoyed all year round!

Top guest favorite

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 Hanford

4.98 out of 5 average rating, 131 reviews

Hanford Minima

Immaculate newly renovated three-bedroom cottage, (2 x double, 1 x twin) 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 village shop and an easy walk over the 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.