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Holiday rentals in Shillingstone

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Top-rated holiday rentals in Shillingstone

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Guest favourite
A charming view of the cottage garden framed by rustic brick walls is enhanced by a rainbow in the background. Lush greenery and colorful plants are visible, creating a serene outdoor space that invites relaxation.
Cottage in Iwerne Courtney

Beautiful Restored Cottage in the heart of Dorset.

A stunning, newly refurbished and tranquil, Dorset holiday cottage. Old School Cottage was built in 1851, and was originally part of the village school. Nestled at the foot of Hambledon Hill, in the village of Shroton, rural rambles are a few steps from the front gate! All the landscape photos shown are only a few metres from the cottage. This is a beautiful place to stay, with a stunning review record. www.oldschoolcottagedorset.co.uk https://www.instagram.com/oldschoolcottagedorset/ ​​​​

4.93 out of 5 average rating, 233 reviews
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.

4.99 out of 5 average rating, 278 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.

4.96 out of 5 average rating, 338 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

4.99 out of 5 average rating, 148 reviews
Top guest favourite
The main living area features a spiral staircase leading to an upper level and an open-plan kitchen with a large island and breakfast bar. Natural light enters through large windows and bifold doors, enhancing the space that includes comfortable seating and greenery.
Home in Stubhampton

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.

4.99 out of 5 average rating, 177 reviews
Guest favourite
The main living space features a warm-toned sofa alongside a dining table set for four. A sturdy wooden ladder leads to the cozy mezzanine area above. Modern kitchenette appliances, including a refrigerator and stove, are visible, enhancing the functionality of the space.
Tiny home in Child Okeford

The Studio: Unique 2-Bedroom Home

The Studio at Framley Orchard is a charming 2-bedroom home with a cozy mezzanine floor. Peaceful but with plenty to do it’s perfect for couples and families of all ages, with a garden featuring swings and climbing trees. You’re in a great spot—our village has an excellent pub, a village shop, and we’re right next to an Organic Farm Shop & Café with incredible food (Wednesday-Saturday). Off-road footpaths lead to the foot of Hambledon Hill. Plus, you’re close to the trailway for cycling too.

4.92 out of 5 average rating, 140 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.

4.96 out of 5 average rating, 186 reviews
Top guest favourite
A bright and inviting bedroom features a spacious king-sized bed dressed in soft linens with decorative cushions. A rustic chest of drawers complements the decor. Natural light filters through a window adorned with delicate curtains, enhancing the warm atmosphere.
Cottage in Stourpaine

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!

4.97 out of 5 average rating, 179 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.
Guest house 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.

4.98 out of 5 average rating, 140 reviews
Top guest favourite
Home in Durweston

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.

5.0 out of 5 average rating, 59 reviews
Top guest favourite
A set of double doors opens to a cozy bedroom area, featuring a bed draped in soft blue linens. Outside, a shaded seating area with a black table and chairs is visible, alongside potted plants, enhancing the serene outdoor setting.
Guest suite in Stourpaine

The self contained Garden Room Annex

The private Annex has it's own access via the rear garden and is connected to the house via a lockable door. The Annex is a bed sitting room with basic kitchen facilities, a shower room and outside area, all for your sole use. You can choose a Large double or 2 single beds in the room. Towels, soap and linen are provided. Teas/coffee/milk available in the room. TV, Fridge, microwave, kettle, toaster, fan, iron/board, plates, cutlery. There's an Airfryer available on request.

4.95 out of 5 average rating, 221 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

4.97 out of 5 average rating, 111 reviews

Popular amenities for Shillingstone holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Shillingstone

Guest favourite
Home in Dorset

Hambledon Hill Cottage with Private Hot Tub

5.0 out of 5 average rating, 12 reviews
Top guest favourite
A view through an open glass door reveals a lush garden with vibrant flowers and greenery leading up to a gently sloping hill. A wooden table with a bouquet of flowers and a candle holder is positioned in the foreground.
Cottage in Iwerne Courtney

Hambledon Hill Views and Sauna

4.94 out of 5 average rating, 64 reviews
Top guest favourite
An aviation-themed holiday home is shown, featuring a blue exterior with a circular insignia. The structure is perched on a gravel area surrounded by green grass, with outdoor seating arranged at a small table. Trees and open countryside are visible in the background.
Tiny home in Okeford Fitzpaine

RAF Mobile Aviation Control Tower

4.96 out of 5 average rating, 82 reviews
Guest favourite
Home in Winterborne Houghton

Dorset Country Home- 6 Bed - Hot Tub

4.94 out of 5 average rating, 31 reviews
Top guest favourite
The entrance features a charming brick façade with large windows, allowing natural light to fill the space. A wooden bench is positioned near the front door, surrounded by potted plants that enhance the welcoming ambiance.
Cottage in Dorset

No1. The Courtyard, Clyffe House

5.0 out of 5 average rating, 98 reviews
Top guest favourite
Cottage in Sturminster Newton

Lovingly restored cottage. Walkable shops and pubs

4.97 out of 5 average rating, 37 reviews
Top guest favourite
Guest suite in Child Okeford

Two bedrooms, shower and breakfast

4.89 out of 5 average rating, 45 reviews
Top guest favourite
The rustic entrance of a charming cottage is framed by lush greenery and vibrant flowering plants. A stone pathway leads to the pale green door, which is accented by a small lantern. The historic brick exterior and the surrounding garden create a welcoming facade.
Home in Winterborne Kingston

Cobblers Cottage, Dorset

5.0 out of 5 average rating, 52 reviews