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Vacation rentals in Winterbourne Steepleton

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Top-rated vacation rentals in Winterbourne Steepleton

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A tranquil garden scene displays lavender plants in the foreground, with vibrant green grass and flowering bushes in the background. A wooden fence is partially visible, framed by trees and clear blue skies, suggesting a peaceful outdoor space.

Guest suite in Portesham

4.85 out of 5 average rating, 189 reviews

Modern living in a Traditional quaint village.

A self contained house attached to owners property. Access via secure garage and own door. Offering privacy in beautiful countryside at the edge of the village with pub/ cafe and shop. Open plan living space with TV/DVD player and log burner for the colder months. Dishwasher and washing machine in the property. 1 Bedroom with sloping ceiling with double or twin beds. Can also accommodate 1 baby (under 2 years to share bedroom). Bathroom with bath and shower. Own small garden with patio area.

Top guest favorite

A paved pathway leads through a lush garden, bordered by wooden fences and surrounded by greenery. A small table and chairs are positioned on the decked area, inviting relaxation. In the distance, the entrance to the Garden Retreat is visible beyond a charming archway.

Tiny home in Dorset

4.97 out of 5 average rating, 103 reviews

The Garden Retreat

The Garden Retreat is a self contained dwelling, at the end of our garden. In a quiet residential area of Dorchester, in the summer there may be some noise from the surrounding gardens. Access from the road, leads directly to the Garden Retreat. We are in easy walking distance (about 10 minutes) from the centre of Dorchester. here you will find Cafes, restaurants and shops Dorchester is an historic town, with many place of interest. No Visitors. No smoking or vaping, on the premises. No pets.

An aerial view showcases the charming stone barn surrounded by greenery. The patio area features outdoor furniture, and a gravel space offers additional parking. A winding path leads from the barn to a secluded road, with lush fields in the background providing a tranquil setting.

Cottage in Dorset

4.94 out of 5 average rating, 248 reviews

Little Barn is a cosy dwelling in a remote valley

Little Barn is located in a remote valley between Upwey and Portesham near Weymouth in Dorset A converted Barn with a modern open plan interior. An adequate garden with Outdoor furniture and BBQ with an external secure store for bicycles etc. The area is good for walking (dogs welcome), many footpaths line the surrounding countryside. Hardy's monument is situated a few miles away. The area offers good cycling both on and off road. Good access to the Dorset coastline which is a short drive away.

Top guest favorite

A wooden sign for 'Shepherd's Hut Parking' is fixed to a post, surrounded by greenery. The sign features leaf designs, providing clear instructions for parking at the hut. The ground is covered with small, white gravel stones, enhancing the natural setting.

Shepherd’s hut in Martinstown

4.97 out of 5 average rating, 178 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 favorite

Guesthouse in Dorchester

4.97 out of 5 average rating, 317 reviews

Lovely, Quiet Studio Annex (with Netflix)

Self contained, self catering studio annex based in the county town of Dorchester. The annex is suitable for 2 adults (a z-bed can be supplied for 1 child under 12). The towns amenities are all within a short walking distance, including the new 'Brewery Square' development. Great base to explore Dorset's fabulous coast, countryside and walk in the footsteps of Thomas Hardy's Casterbridge. Motorbike friendly, high chair & travel cot available. Complimentary tea and coffee. Netflix TV.

Top guest favorite

A tree-lined pathway is framed by vibrant green foliage, leading towards a wooden gate in the distance. The sunlit scene showcases a blend of grass and wildflowers along the edges of the path, inviting a sense of tranquility.

Home in Wynford Eagle

4.92 out of 5 average rating, 258 reviews

Swallows Return - Alpacas-Gardens-Brook-Tennis

Nestled in an area of Outstanding Natural Beauty, Wynford Eagle is one of West Dorset's hidden gems. Swallows Return is a cosy studio retreat, a haven for peace and relaxation which opens out onto a large terrace with stunning views of the valley, 8 acres of grounds and gardens and beautiful alpacas. A great base to explore Dorset, situated just 15 minutes from the Jurassic coastline and all this incredible area has to offer. Please also see listing for airbnb.com/h/woodpeckers-rest

Top guest favorite

A charming stone cottage with a sloped roof is showcased under a blue sky with clouds. The upper balcony features seating, and a gated pathway leads to the entrance. The structure is complemented by surrounding greenery and the roof of an adjacent building.

Cottage in Dorset

4.98 out of 5 average rating, 312 reviews

The Old Apple Store, Bridport and Jurassic Coast

Our cottage is nestled in the heart of the Bride Valley close to the Jurassic Coast. This converted barn has views over our orchard. The cottage is 20 minutes drive from Dorchester and Bridport. 40 minutes to Durdle Door. Upstairs kitchen area with cooker, fridge, washing machine, lounge area with lots of books, DVD ‘s. Dining area and balcony with seating. Downstairs Large bedroom with King Size bed. Bathroom with shower. Outside pretty walled garden with seating.

Top guest favorite

Rows of lush vines extend through the vineyard, bordered by gentle green hills and trees. A clear blue sky is visible above, enhancing the natural beauty of the surrounding landscape.

Shepherd’s hut in Waddon

4.97 out of 5 average rating, 241 reviews

The Hide on the Vineyard with wood fired hot tub

'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 adults Everything you see in the photos are for your own exclusive use - no sharing - your own corner of a beautiful little vineyard! A perfect place to relax in a romantic setting for two Enjoy beautiful sunsets over the vines whilst soaking in your own private wood fired hot tub which has a small extra charge of £50 per stay

Top guest favorite

A charming converted garage is depicted under a blanket of snow, with the front entrance framed by a light blue door. Snow-covered trees and shrubs, including a vibrant orange bush, add color to the serene winter scene. A clear pathway leads to the entrance, creating an inviting approach.

Guest suite in Sydling Saint Nicholas

4.97 out of 5 average rating, 211 reviews

Waterside. Sydling St Nicholas.

This property is a beautifully converted garage. It is detached at the front of the property and you have complete privacy. You can park your car directly in front of the Airbnb where there is seating for Airbnb use only. It is a very quiet village and at night if you switch all the lights off and it is a clear night you can see the Milky Way. If you are staying with us for a special occasion: birthday, anniversary , etc. Let me know and I will try to make your stay special.

Top 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, 174 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.

Top guest favorite

A panoramic view of a tranquil cove reveals gently sloping hills on either side of the beach. Clear blue waters contrast with the sandy shore, where people are seen lounging and enjoying the sun. Boats are anchored in the bay, providing a picturesque coastal scene.

4.98 out of 5 average rating, 126 reviews

Cheerful one bedroom home in the heart of Dorset

A great base for exploring Dorset and centrally-located. This newly decorated self contained 1 bedroom annexe has a fully equipped kitchen & in the county town of Dorchester, the birth place of Thomas Hardy. It is a perfect base to explore the beautiful countryside and Jurassic coast! The town’s amenities are only a short walk away including the new Brewery Square development. Complimentary tea and coffee also provided.

Top guest favorite

Home in Cruxton

4.98 out of 5 average rating, 193 reviews

Kingfisher Lodge with Private Riverbank

A beautiful Lodge set in 7.5 acres with its own riverbank, situated down a Dorset country lane. Set amongst fields, the tranquil, peaceful surroundings make the accommodation perfect for those who want to get away. Devoid from light pollution, the sweeping skies make it an ideal spot for star gazing. The Jurassic Coast is only a short drive, with beautiful coastal walks. A perfect break!

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Popular amenities for Winterbourne Steepleton vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Winterbourne Steepleton

Top guest favorite

A rustic exterior of a dark wooden structure is highlighted, featuring a small door and a stacked woodpile adjacent to the entrance. Colorful flowers in bloom are visible in the foreground, framing the scene with vibrant hues, while greenery and blue skies create a serene backdrop.

Apartment in Rodden

5 out of 5 average rating, 29 reviews

Wooster - Jurassic Coast

JennieRating, 5 stars1 day ago

The perfect home away from home for a few days 😊 the location is beautifully secluded, with a gorgeous garden and drivable to Weymouth and other local beauty spots. Louisa is a lovely host adding a couple of little extras on our arrival and allowing flexibility on our check out. Would highly recommend!

Top guest favorite

The cottage exterior is surrounded by a lush garden filled with blooming flowers in shades of white and purple. The rustic stone and brick façade is complemented by quaint windows. A welcoming entrance leads to the interior, enhancing the cottage's tranquil charm.

Cottage in Cerne Abbas

4.98 out of 5 average rating, 64 reviews

Pilgrims Cottage-Luxury Grade 1 Listed cottage

KarenRating, 5 stars2 weeks ago

Beautifully restored home in the most extraordinary location - opposite the Church, and with the remains of the ancient Abbey just down the road. Everything in the house is the finest quality - even the hairdryers are GHD! You’ll be very comfortable. Pollyanna was a perfect host. Three characterful pubs in this small, quaint town, and just a 15 minute drive to Dorchester (go to the Curiosity Centre!). Would very happily stay again.

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

4.98 out of 5 average rating, 86 reviews

Enchanting Manor Coach House

SusanRating, 5 stars1 month ago

We thoroughly enjoyed our stay. The Coach House was well-appointed with everything we needed. The location was so peaceful with only the birdsong to listen to. We loved being able to walk straight out to the hills and enjoy the beautiful countryside. The local pub is really friendly with great food. The accommodation was really comfortable, clean and we would love to stay again. Thank you.

Top guest favorite

The modern bathroom features sleek grey tiles on the walls and floor, complemented by wooden beams overhead. A wall-mounted sink and a toilet occupy one side, while a glass shower with overhead rain shower head is situated opposite, ensuring a minimalist aesthetic.

5 out of 5 average rating, 67 reviews

Artist’s Creative Hideaway & Sauna

ChloeRating, 5 stars2 weeks ago

Really lovely stay - very private, clean and comfortable. Lovely outdoor fire area. Bev was really friendly, replied super fast and use of the sauna was a bonus. Thank you Bev for the most wonderful stay.

Top guest favorite

A modern Nespresso coffee machine is positioned on a sleek black countertop. A circular drip tray rests in front of the machine, accompanied by colorful coffee pods in yellow, red, and blue, alongside a silver coffee capsule. White tiles create a clean backdrop.

Condo in Dorset

4.99 out of 5 average rating, 78 reviews

Large 2 bedroom town centre flat with free parking

DavidRating, 5 stars3 days ago

We had a great stay! The apartment is opposite a beautiful park and it’s easy to walk into town. The parking space was a very useful bonus. The place was impeccably clean with comfy lounge furniture. All the little extras make it so convenient and just make all the difference! Thanks Steve and Santina.

Top guest favorite

A modern kitchen equipped with light-colored cabinetry and a wooden countertop. Stainless steel appliances are visible, including an oven and a hood. A glass door leads to a conservatory with a dining area. The warm wood flooring adds to the welcoming feel of the space.

Apartment in Dorset

4.97 out of 5 average rating, 32 reviews

Welcome to Fox Corner

NatashaRating, 5 stars1 week ago

Clare was lovely. Very friendly and loved the little touches like milk and cookies and a select breakfast granola. Nothing was too much trouble like an early check in. Had an amazing time and great place to stay walking distance to town and restaurants. Would highly recommend to stay here ❤️

Top guest favorite

A seating area features a wooden coffee table with a glass candle holder at its center. A cozy chair with a patterned design is visible, along with a small side table that holds a light source. Large glass doors offer a view of verdant greenery outside.

Cabin in Frampton

5 out of 5 average rating, 26 reviews

Moorhen cabin

LaurenRating, 5 stars1 week ago

The cabin is a beautiful, peaceful little haven of tranquility we wish we'd have booked for longer (and will definitely be back!) But, what made our stay so much more unforgettable is our fabulous host Carolynn! When I booked I contacted to explain it was for our wedding; Carolynn got straight back to me, asked if there was anything we needed I immediately knew I'd booked with the right person, felt completely at ease about our stay (a big relief with major wedding stress!) Carolynn went above and beyond with extra special little touches to make it even more amazing! (Thank you so much for our lovely card, bottle of champagne and home made brownies!) We couldn't have asked for a better, more welcoming host!

Top guest favorite

A small dining area features a wooden table accompanied by two woven chairs. Framed artwork adorns the walls, complementing the warm tones of the wooden flooring.

Cottage in Dorchester

4.98 out of 5 average rating, 53 reviews

The Granary - a peaceful, rural location.

JohnRating, 5 stars1 month ago

We had a super four day stay at the Granary with our Cocker spaniel. The accommodation was comfortable and everything was as described and the hosts were welcoming and friendly. We enjoyed the peace and quiet of the area and used it as a base for discovering the beautiful county of Dorset. We will hopefully be back.

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