Holiday houses in Winterbourne Steepleton

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Top-rated holiday rentals in Winterbourne Steepleton

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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 out of 5 average rating, 135 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 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, 109 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.

Guest favourite
Apartment in Winterbourne Abbas
4.84 out of 5 average rating, 45 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

Guest favourite
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, 293 reviews

The Old Reading Room West Stafford, Dorset.

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.

Superhost
Guesthouse in Dorset
4.89 out of 5 average rating, 587 reviews

Secluded Garden Lodge with Private Hot Tub

The Lodge Retreat is nestled at the bottom of a secluded garden pathway in the sleepy suburb of Southbourne and is a stones throw from Bournemouth’s award winning beaches. The whole of the Lodge Retreat is yours to relax and unwind and includes use of your own private hot tub. There’s plenty of free street parking and more often than not, you can get the street space directly outside of the property. The Lodge Retreat offers an easy self check in and check out service for your convenience.

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
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, 447 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.

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, 136 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 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, 203 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

Top Guest favourite
A charming wooden shepherd's hut is nestled among greenery, featuring a wooden deck with a small dining table and chairs. Steps lead up to the entrance, while a storage unit and lawn area with flowering plants enhance the outdoor space.
Shepherd’s hut in Martinstown
4.98 out of 5 average rating, 208 reviews

Romantic Shepherds hut with private garden

Nestled in a quiet wooded corner of our garden on the edge of the village of Martinstown. Fully self contained, the hut has everything you need inside and is in a great central location, close to Dorchester and just a short drive to Weymouth and Chesil beach. Fantastic walks, bike rides and lovely Jurassic coast beaches are nearby. We love to share our beautiful little corner of Dorset with both new guests and those of you have have stayed before. Check out our wonderful reviews!

Top Guest favourite
A former aircraft, showcased in a woodland setting, features a unique exterior design with vibrant green accents. The fuselage stands on a grassy area, surrounded by trees and green foliage, with a pathway leading up to it, indicating accessibility to the entrance.
Plane in Somerset
4.99 out of 5 average rating, 144 reviews

No Snakes on this Plane!

Tired of economy class? Charter a stay in a first class fuselage with wood fired hot tub situated in tranquil woodland. Welcome onboard your own private aircraft, step inside to the sleek contemporary interior of first class. Outside, unwind in seclusion in private woodland, a short walk away from the West Somerset Railway and the AONB of the Quantock Hills. An ideal getaway for two in first class, for families there is a bunk bed in the living room area. Dogs at additional cost.

Top Guest favourite
Guest suite in Somerset
4.99 out of 5 average rating, 110 reviews

The Ops Room, Ground floor 2 bed Apartment

Observatory House is a converted cold war nuclear bunker. **** We are currently having our roof replaced but this work is overrunning Due to this we have scaffolding erected across the front of the building. If you book we will send a reduced price option to you to accept/decline as a gesture of goodwill for any inconvenience caused****. Pin coded lock box allows flexible self check-in and out so you can come and go as you please. Pets allowed but no cats due to allergies

Popular amenities for Winterbourne Steepleton holiday rentals