Holiday rentals in Shillingstone

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Top-rated holiday rentals in Shillingstone

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Top guest favourite
The exterior of the cottage is highlighted by its stone and brick façade, framed by greenery. A solid wood door with glass panels offers an inviting entrance. Windows allow natural light to enhance the warm tones of the building, situated along a quiet lane.
Cottage in Sturminster Newton
5.0 out of 5 average rating, 105 reviews

Unique Cottage with Private garden

The Sexton's cottage was restored to a high standard, bringing the charm of the original cottage with that of modern day living. There is a light and airy living, dining & kitchen area upstairs, with a double bedroom and Shower room downstairs. The cottage has a large private south facing garden with a dining area under a pergola, along with a BBQ and a raised decking area ideal for your morning cup of tea or an evening drink. Sturminster Newton is well positioned to explore Dorset and Somerset.

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
4.93 out of 5 average rating, 232 reviews

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/ ​​​​

Top guest favourite
A luxury hot tub filled with bubbling water welcomes relaxation, framed by lush greenery and open fields under a clear blue sky. The spacious area includes a basketball hoop for added enjoyment, creating an inviting outdoor atmosphere.
Guest house in Tarrant Gunville
4.88 out of 5 average rating, 209 reviews

The Retreat ~ Hot Tub~ Sauna ~ Charming & Cosy Gem

Step into the stylish and comfortable 1BR 1Bath guest house nestled in the picturesque village of Tarrant Gunville. It offers a relaxing oasis with a luxury hot tub, sauna, and a perfect base to explore natural attractions and historical landmarks of Dorset County. Modern design and a rich amenity list will satisfy your every need. ✔ Comfy BR with a Double Bed ✔ Bright Living Space ✔ Kitchenette Amenities ✔ Garden ✔ Hot Tub ✔ Sauna ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Free Parking See more below.

Top 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
4.99 out of 5 average rating, 147 reviews

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

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
4.99 out of 5 average rating, 174 reviews

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.

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
4.92 out of 5 average rating, 140 reviews

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.

Top guest favourite
The exterior of Willow Brook Barn showcases a charming wooden facade with a mix of wood and brick. Lush greenery surrounds the property, and a gravel path leads to the entrance. Clear blue skies complete the serene countryside setting.
Guest house in Okeford Fitzpaine
5.0 out of 5 average rating, 37 reviews

Delightful barn in scenic North Dorset

Welcome to Willow Brook Barn, a beautifully appointed two-bedroom property on a no-through lane in Okeford Fitzpaine. Nestled at the foot of Okeford Hill in North Dorset's stunning countryside, this cosy retreat offers comfort and tranquillity. The village provides essentials, including a pub, shop, and Post Office. Adjacent to the owner's home, it ensures privacy and a friendly atmosphere. Enjoy peaceful mornings and relaxing evenings on the private terrace. Ideal for exploring or relaxing.

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
4.97 out of 5 average rating, 177 reviews

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!

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
4.98 out of 5 average rating, 135 reviews

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.

Top guest favourite
Home in Durweston
5.0 out of 5 average rating, 58 reviews

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.

Top guest favourite
Earthen home in Dorset
4.98 out of 5 average rating, 53 reviews

Wellness retreat, Sauna & Hot Tub - Shaftesbury

Melt your stresses away swinging in a hammock,soaking in a hot tub or laying back in a Sauna.Escape the buzz of modern life unwinding in your own idyllic space. Enjoy a massage surrounded only by views. Angels Hut nestles into a hill overlooking Shaftesbury. It's situated amongst a 65 acre farm with woodland’s, and wild deer, with animal welfare and sustainability at its core.Let the owls serenade you providing a perfect backdrop to a blissful night you will remember for years to come!

Top guest favourite
An open living area features a modern, plush sectional sofa facing a large glass wall that connects to the outdoor space. Two small, round tables, one with a decorative tray, are positioned in front. Natural light fills the room, highlighting the simple decor.
Bungalow in Somerset
4.99 out of 5 average rating, 293 reviews

Modern & spacious house in the countryside.

The Pavilion is a modern, purpose built holiday house in the quiet Somerset village of Yarlington. It has all the conveniences: Wood burning stove, underfloor heating, Washer & tumble dryer, Iron & ironing board, fast fibre optic broadband and a charging station for an electric or plug in hybrid car, but sadly the mobile phone signal is very poor. The house is next to the pub and a stones throw from the church. The Newt and Hauser Wirth Gallery in Bruton are within a 15 minute drive.

Popular amenities for Shillingstone holiday rentals