Holiday rentals in Winterbourne Steepleton

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Top-rated holiday rentals in Winterbourne Steepleton

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Cottage
4.87 out of 5 average rating, 102 reviews

The Coach House, Duntish Mill Farm, EV Charging

Whether you're exploring Dorset's countryside and coastline or simply looking to switch off for a few days The Coach House offers a peaceful escape for two. Beautifully renovated it combines exposed beams, a cosy wood-burning stove and a luxurious walk-in rainfall shower with plenty of space to relax and unwind Set within Duntish Mill Farm between Sherborne and Dorchester and within easy reach of the Jurassic Coast, it's the perfect base for discovering some of Dorset's most beautiful landscapes

Top guest favourite
A cozy sitting area features a plush olive green velvet sofa adorned with patterned and solid cushions. A stylish wooden chair complements the vintage aesthetic, while large artworks decorate the walls. Exposed wooden beams add character, and a patterned rug enhances the inviting ambiance.
Barn
5 out of 5 average rating, 128 reviews

Artist’s Creative Hideaway & Sauna

Beautiful, inspiring, and peaceful, Arthouse is a place to escape. This converted art studio in West Dorset is close to Chesil Beach and the Jurassic Coast. It is surrounded by wildflowers and features contemporary art and sculptures by artists Rouwen and Reeve. The space is complemented by mid-century modern furnishings, high ceilings, and exposed beams. All doors open to a private patio and a naturalistic garden. The Sauna, located in the gravel garden looks out onto sculptures and plants.

Guest favourite
Flat
4.86 out of 5 average rating, 28 reviews

Private self contained flat

Perfect location self contained private flat, 10 minutes from Weymouth, 5 minutes from Dorchester, 14 minutes from Bridport, private parking directly in front of the flat outside dining area! Brand new totally refurbished.Double bed, and double sofa bed, 55” TV can be pulled out, WFi, heating , hot water, large kitchen with dinning breakfast bar, and second Tv, electric oven, Hob,toaster, microwave,kettle,fridge, sink. Shower room, power shower, lighted mirror with shaving point, wc and vanity.

Top guest favourite
An open living space features a warm color palette with stone walls and wooden beams. A leather sofa is positioned in front of a wood-burning stove, enhancing comfort. A dining area with two chairs is visible, as well as a well-equipped kitchen with modern appliances.
Barn
5 out of 5 average rating, 93 reviews

The Cowshed, Washing Pool Barns - suite for two

Luxurious Dorset village suite for two. Quality conversion of a listed stone barn into a completely equipped ground floor self-catering suite in the Dorset AONB. A couple of miles south west of Dorchester Washing Pool Barns are in the heart of Martinstown village, just a one minute walk from the local pub and maybe five minutes walk to the village store and post office. Bridleways, cycle routes and public footpaths are on the doorstep with the Jurassic coastline around five miles further south.

Top guest favourite
Shepherd’s hut
4.98 out of 5 average rating, 281 reviews

The Hide with Private Wood Fired Hot Tub option

'The Hide' is a truly romantic hideaway on an English Vineyard with your own Shepherd's Hut, Cabin, Shower Room & Private Wood Fired Hot Tub for two - there is a £50 fee for the wood fired hot tub Please be aware the Airbnb Guest Service Fee of 12.5% is now included in our prices Everything you see in the photos are for your own exclusive use Enjoy beautiful sunsets over the vines whilst soaking in your own private wood fired hot tub A perfect place to relax in a romantic setting for two

Top guest favourite
A spacious sleeping area features a cozy king-size bed adorned with decorative pillows. Large windows allow natural light to fill the room, complemented by light hardwood flooring. A small dining table with chairs is positioned nearby, enhancing the inviting atmosphere.
Guest suite
4.92 out of 5 average rating, 279 reviews

Discover Little Drey: Your Perfect Getaway

At Little Drey, you'll find comfort, and warm hospitality, all while being conveniently close to Dorchester. A variety of restaurants, cafes, and shops are all within walking distance. Close to some of the best places to visit in Dorset, and within easy reach of famous beauty spots and amazing places to visit. Parking on property along with self-check-in, makes it super easy to have a relaxing, enjoyable break. Your host lives next door and is on hand to make your stay the best possible.

Top guest favourite
A stone cottage features a light green door framed by greenery. Large windows allow natural light to illuminate the entryway, while shrubs and trees create a peaceful, sheltered setting. The roofline peaks gently against a backdrop of clear blue skies.
Home
4.96 out of 5 average rating, 126 reviews

Enchanting Manor Coach House

An elegant, relaxed home in the grounds of the Manor in this AONB with walks directly from the house. The pretty village of Winterbourne St. Martin (Martinstown) has a great pub and a super village shop both within a short walk. Close to the Jurassic Coast and spectacular country views, its the perfect place to chill after a walk, a day at the beach (approx five miles away) or visiting the many attractions in and around Dorchester. Guests have a private garden, and access to a tennis court.

Top guest favourite
A cozy bedroom is presented with a wooden bed featuring crisp white linens and decorative pillows. A light-colored dresser is positioned nearby, complemented by a small lamp. Natural light filters in through patterned curtains, enhancing the serene atmosphere.
Tiny home
4.99 out of 5 average rating, 196 reviews

Cosy private Loft overlooking Dorset countryside

Nestled in the heart of the Dorset countryside, The Loft is your ideal 'getaway'. From stunning views to a comfy king-size bed, this cosy space will provide you with everything you need to relax. Open the stable door, and listen to the birds, reconnect with nature while sipping coffee and tucking into a selection of breakfast options provided upon your arrival. With an abundance of local amenities, please see the guide for my favourite secret spots! We look forward to welcoming you!

Guest favourite
The entrance features a maroon double door with decorative panels and shuttered windows. A small green table and chair set are positioned on the patio, surrounded by potted plants with blooming flowers. A house number plaque is mounted nearby.
Apartment
4.89 out of 5 average rating, 106 reviews

Studio with off-street parking, private entrance

Welcome to our bright studio with gated off-road parking and free fibre (160 mbps) wi-fi. We welcome all to enjoy a stay in Dorset. We are a ten minute walk from the station, Poundbury and Brewery Square. Our newly renovated studio has an inviting interior, a rainfall shower and dedicated office space. A small double bed will provide a comfortable nights sleep. Dorset’s motto is “who’s afeard “ so what will you discover? The Cerne Giant, the chocolate factory ? Minimum stay two nights

Top guest favourite
Barn
5 out of 5 average rating, 222 reviews

Jurassic Coast Boutique Retreat with Views

Set amid the rolling Dorset countryside with far reaching breathtaking views The Hayloft is a relaxed luxury retreat designed for slow, restorative stays. Part of Grandview Farm The Hayloft is a self contained annex offering a secluded, peaceful haven just moments from the Jurassic Coast. Thoughtfully styled with natural textures and luxurious touches throughout, it is the perfect base for a couple or two friends who enjoy coastal walks, cosy mornings and drinks under the stars.

Top guest favourite
The exterior of the farmhouse is shown, featuring a traditional stone construction with multiple windows. Lush green foliage surrounds the base, and the building stands against a clear blue sky, offering a glimpse of the rural landscape surrounding the property.
Home
4.97 out of 5 average rating, 35 reviews

Hardy View Farm House

The house is set in the heart of Dorset countryside celebrating lives of Thomas Hardy, Nelson’s admiral, his birthplace in next village and his monument in full view of the house. The house of the other Thomas Hardy - writer of many English classics - is 6 miles away and open for public viewing. The farm sits on the old Roman Road with Roman burial grounds, Jurassic coast and seaside resort of Weymouth within easy reach as well as the Isle of Portland whose stone built London!

Guest favourite
Cottage
4.86 out of 5 average rating, 188 reviews

Cosy, dog friendly cottage in the heart of Dorset

Take it easy at this unique and tranquil getaway in the heart of Dorset. Beautiful scenery is all around you in this cosy cottage. The Jurassic coastline a just a short drive away, as is the historic town of Dorchester. The village has a great local pub, and a shop selling local produce as well as some essential items. Enjoy the privacy of an entire home with a beautiful garden in picturesque surroundings.

Popular amenities for Winterbourne Steepleton holiday rentals