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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Top guest favourite
The cabin's exterior features a welcoming deck area with a wooden table and chairs, shaded by a canvas awning. Soft-colored front doors create a contrast against the dark wooden structure. Lush greenery surrounds the cabin, enhancing the peaceful countryside setting.
Cabin in Dorset
4.97 out of 5 average rating, 106 reviews

Cosy Country Cabin

The Cabin is situated on our land, next to our garden. It faces down the valley with scenic views and a peaceful setting. It's an ideal place to relax and a great base from which to explore the beautiful Dorset coast and countryside. If you like wildlife you may spot deer, hares, kestrels, buzzards, barn owls. It's open plan with a light and pleasant lounge space, sleeping nook containing a very comfortable double bed, kitchen with a fridge/freezer and 2 ring gas hob and a compact shower room.

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 in Dorset
5.0 out of 5 average rating, 131 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 in Winterbourne Abbas
4.86 out of 5 average rating, 36 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
Shepherd’s hut in Portesham
4.98 out of 5 average rating, 282 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

Guest favourite
An indoor pool area is presented under a wooden-beamed ceiling, featuring exposed brick walls. Soft lighting creates a calm ambiance around the clear water of the pool. A cozy seating area is visible in the background, adding to the overall relaxation space.
Home in Osmington
4.86 out of 5 average rating, 130 reviews

Large coastal cottage with spa and private pool

Set in a prime position amidst a quintessential village of thatched cottages. Where wildflower paths and trickling streams amble down the the beautiful Osmington Bay. Toe dipping in the shallows, coastal walks under flaring sunsets, hibernating in our home spa while storms crash outside. Our unique holiday home offers a sanctuary in all weathers. With a collated & collected vibe, this light filled cottage is perfect for families looking for a beach escape, only a 5 minute drive to the sea.

Top guest favourite
A charming cabin is nestled among lush greenery, with a balcony that overlooks a serene pond and garden. The landscape features a variety of plants, including palm trees and ornamental shrubs, creating a natural and peaceful setting.
Cabin in Dorchester
5.0 out of 5 average rating, 104 reviews

Moorhen cabin

Sit back and chill in this calm, stylish space. Moorhen is a newly refurbished cabin in the owner's grounds. Surrounded by open countryside and sitting directly on a bridleway/cycle route 26. It comes with use of the owner's tennis court, boules court and riverbank. In addition to the balcony some areas of the main garden are also for guest use . Within easy reach of Dorchester, Weymouth and the world famous Jurassic coast. Moorhen provides a peaceful base for you to take it easy and explore

Top guest favourite
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, 117 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 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 in Martinstown
4.96 out of 5 average rating, 130 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.

Guest favourite
A person sits in a small boat on a clear, calm waterway surrounded by lush greenery. The boat is gently gliding through the water, with vibrant foliage reflecting in the serene surface. Wildlife may be observed in this tranquil setting.
Cottage in Portesham
4.76 out of 5 average rating, 445 reviews

Pond outside your bedroom window.

Self-contained bedroom, a sitting room and shower room. Your suite of rooms is separate from the house with its own entrance. The windows overlook the village duck pond and spring and pretty waterfall. There is parking, for your car, at your door. We're in a Dorset village with Trafalgar history, centuries old church, busy pub. The coast is only a couple of miles away. We are on the Dorset Coastal Path and the SSSI Jurasic Coast. £7.50 for a full Dorset breakfast. Evening meal £7 to £12.

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 in Dorchester
4.91 out of 5 average rating, 287 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 charming shepherd's hut is surrounded by trees, illuminated under a starry sky with visible trails of stars. The structure features a small window and a deck with simple white chairs. The rustic charm is accentuated by the natural landscape surrounding the hut.
Shepherd’s hut in Dorset
4.97 out of 5 average rating, 115 reviews

Romantic Tree Cabin - Bride Valley- Jurassic Coast

Lapin Cottage is nestled in the most beautiful pocket in Dorset. Situated on private farm land, it hosts rolling views of the Bride Valley and only a stones throw from the Jurassic Coast. Every comfort has been thought of in this cosy, romantic shepherd's hut. A luxuriously soft bed, fully equipped kitchen and bathroom. You will wake up to a chorus of birdsong and the tinkling of bells from our sheep. The sunken bath on the deck is the ideal place for gazing up at the starry night sky.

Guest favourite
A charming barn conversion features natural stone walls and large windows that invite ample sunlight. The surrounding landscape includes lush greenery and a clear blue sky, creating a serene rural atmosphere. The driveway leads to the entrance, providing easy access to the property.
Cottage in Dorset
4.8 out of 5 average rating, 201 reviews

Stunning Barn conversion with heated swimming pool

Courage Cottage is a two bedroom detached barn conversion in a Georgian farmyard.The barn was converted in 2013 so has all modern conveniences including underfloor heating. It is very individual and situated in a quiet , rural setting. It has two bedrooms with en-suite bathrooms. The village of Martinstown has an excellent pub and shop. Dorchester is 2 miles away and has every facility including good rail connections in all directions.Swimming pool (shared ) open May 15th-Sept 15th

Popular amenities for Winterbourne Steepleton holiday rentals