Vacation rentals in Winterbourne Steepleton

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Top-rated vacation rentals in Winterbourne Steepleton

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Top guest favorite
Barn in Dinton
5 out of 5 average rating, 164 reviews

Unique, romantic luxury countryside retreat

Unique luxury cottage for two, an ancient dovecote with a fabulous swimming pool. Beautifully furnished, romantic and spacious, in gorgeous peaceful countryside, the thick stone walls make it warm and cosy in winter, cool in summer as well as quiet and private. Upstairs there is a very comfortable super kingsize bed, a rolltop bath, a huge velvet sofa and a 50" TV. Downstairs is a shower room, kitchen and large dining area. Lovely walks from the door and close to Salisbury, Longleat & Stonehenge

Guest favorite
A charming stone cottage is surrounded by lush greenery and various colorful flowering plants. A small white table and two chairs are placed outside, inviting guests to enjoy the garden view. The cottage features a traditional door framed by vibrant foliage.
Cottage in Dorset
4.97 out of 5 average rating, 672 reviews

Cute, Cosy & Stylish Bothy Cottage, near Sherborne

Stylish, Comfortable & Quirky - “Top 10 Dorset Airbnb” (Conde Nast Traveller) in a “Top 50 UK Village” (Sunday Times). The Bothy is a detached stone cottage where you can share some free Prosecco on your private terrace. It is in the rural historic Yetminster Conservation Area with a thatched pub, café & shop. It is next door to a quintessential "Chocolate Box" thatched cottage. You are on the edge of the Dorset Area of Outstanding Natural Beauty with good access to the sea & Jurassic Coast.

Top guest favorite
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 in Dorset
5 out of 5 average rating, 117 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.

Top guest favorite
A modern A-frame house is framed by a vibrant garden featuring tall grass and clusters of purple flowers. Large glass windows provide a view into the warmly lit interior, showcasing a cozy ambiance. Surrounding trees create a natural backdrop to this inviting space.
Place to stay in Lympsham
5 out of 5 average rating, 232 reviews

Romantic Somerset hideaway

Hello! We are Rob and Kate and we have poured our heart and soul into our guest house. Tucked away on the outskirts of sleepy Lympsham, enjoy the countryside around you whilst resting your legs after walking the renowned mendips. Enjoy a glass of wine whilst watching the many birds in the surrounding trees or be a little more adventurous with the numerous local cycle routes. We look forward to meeting you on your stay. Shared driveway next to main house. Not suitable for children or pets.

Top guest favorite
The exterior of the Victorian Reading Room is presented, showcasing a charming brick facade with light moss present on the roof. A welcoming entry door, framed by two chimneys, is complemented by modern windows. A vintage-style post box is positioned beside the entrance.
Tiny home in West Stafford
4.92 out of 5 average rating, 279 reviews

The Old Reading Room West Stafford

The Victorian Reading Room of West Stafford is of historical importance. Used before the war as a Reading Room for the villagers and estate workers, the newspapers were provided, the village shop in the late 1930s, then a workshop and a store room for the church. We have now lovingly restored, decorated and furnished this amazing building into a cosy self catering holiday retreat, "far from the madding crowd" Open plan, comfy double sofabed, wood burner, country walks and fabulous village pub.

Top guest favorite
Shepherd’s hut in Waddon
4.98 out of 5 average rating, 275 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 favorite
A well-lit living area is shown, featuring a light green wall and a comfortable sofa positioned near a window. A small wooden table with two chairs is visible, alongside a decorative round rug on the floor. A bedside lamp and a wall-mounted shelf complete the space.
Home in Martinstown
4.97 out of 5 average rating, 109 reviews

Guest Suite in Martinstown

Recently converted guest suite in a house situated in the middle of a picturesque village in Dorset. Private access through your own front door and set aside from the main house to ensure privacy. Private area outside for your use or you are welcome to explore the extensive gardens and woodland. Cooking facilities are limited but fridge, microwave, electric hob, toaster and kettle are supplied. Good food is served in the village pub a short stroll away. Dorchester town is a 10 minute drive.

Top guest favorite
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 in Dorset
4.92 out of 5 average rating, 269 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 favorite
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 in Martinstown
4.97 out of 5 average rating, 118 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 favorite
The exterior of the barn reveals a charming blend of traditional stonework and wooden features, characterized by a large front door and multiple windows. Surrounding the entrance are well-maintained plants and shrubs within a curved brick border, contributing to a welcoming appearance.
Barn in Dorset
4.93 out of 5 average rating, 201 reviews

Lynchett Chase Barn in beautiful West Dorset

This Dorset stone barn has been modernised to provide spacious, open plan living. The property is ideal for large family holidays, and celebrations. The ample rear garden has a games room with table tennis table, perfect for children to let off steam! The barn is situated in the pretty village of Maiden Newton, which has great local shops and eating within a 5 minute walk and is just 30 minutes from the stunning Jurassic Coast, with the beautiful Dorset countryside right on the doorstep.

Top guest favorite
A modern kitchen features a wooden dining table surrounded by four woven chairs. A large range cooker is positioned against the tiled backsplash, with ample white cabinetry overhead and below. Open shelving displays glassware and decorative items, complemented by soft lighting and a neutral-colored floor.
Cottage in Dorset
4.94 out of 5 average rating, 233 reviews

Strawberry Cottage

Lovingly restored and modernised by Harry in 2011, Strawberry Cottage is nestled by the river Wey in the village of Upwey, Dorset. This quaint property is close to the famous Jurassic Coast, within 4 miles of the seaside town of Weymouth and Dorchester town.Durdle Door / Lulworth Cove is an approximate 29 minute drive,and the main supermarket is 8 minutes away by car. Upwey has two pubs a busy tearoom,garden nursery and Tesco Express all within 5 to 10 minutes walk. Relax inside or out.

Guest favorite
The exterior of a charming stone cottage features a slate roof and a white door framed by a small garden. Flanking the door, two wooden chairs invite relaxation, while climbing plants add greenery to the facade. Natural light highlights the rustic textures of the stone walls.
Guest suite in Long Bredy
4.93 out of 5 average rating, 189 reviews

Stylish hayloft conversion next to 18thC farmhouse

A newly converted hayloft set up as a one bedroom house. Pitched, beamed ceiling in bed/sitting room, own kitchen downstairs. Spacious shower room, separate small WC No TV but WiFi. Private entrance from village lane into property. In the heart of the Bride Valley so perfect for all year round walkers and nature lovers. Jurassic Coast 5 miles away. One of the richest areas in the UK for hill forts and ancient earthworks. Very houseproud so regrettably no pets and no smokers.

Popular amenities for Winterbourne Steepleton vacation rentals