Vacation rentals in Winterbourne Steepleton

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Top-rated vacation rentals in Winterbourne Steepleton

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Top 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, 632 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

The exterior of a late Victorian house is shown, featuring a brick facade with decorative elements. The property is surrounded by well-maintained greenery, including a lawn and trees. Several windows, evenly spaced, provide views into the building, complementing the architectural details.

Condo in Dorset

4.99 out of 5 average rating, 103 reviews

Large 2 bedroom town centre flat with free parking

Located overlooking Dorchester’s beautiful, tranquil Borough Gardens, this very spacious two bedroom flat provides the perfect place to enjoy a break in splendid Dorset’s historic county town. The property is only a two minute walk from the main high street of the town with its shops, museums and historic buildings. It is also within easy, level walking distance to the two train stations and many bus routes. A free parking space included allows guests to visit all areas of the county with ease.

Top guest favorite

An open plan living space features a green sofa, wood-burning stove, and a dining table surrounded by wooden chairs. The exposed brick wall adds character, while a patterned rug anchors the seating area. Natural light enters through a window, creating a bright atmosphere.

Guest suite in Portesham

4.86 out of 5 average rating, 197 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.

Guest favorite

The exterior view of the converted barn is presented, showcasing the stone structure surrounded by lush greenery. A gravel driveway leads to the property, with an outdoor seating area visible. Neat hedges outline the garden, offering a sense of privacy amid the scenic countryside.

Cottage in Dorset

4.95 out of 5 average rating, 255 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 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, 107 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, 238 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.

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, 100 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 favorite

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

4.97 out of 5 average rating, 193 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

The wood-fired hot tub, crafted from cedar, is positioned under a wooden shelter, offering a view of the vineyard and sunset. The serene water surface reflects the trees and warm evening light, providing a tranquil setting for relaxation.

Shepherd’s hut in Waddon

4.97 out of 5 average rating, 251 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

An open-plan living area features a spacious bed adorned with a floral-patterned duvet. A comfortable sofa and coffee table are visible, with bifold doors leading to a terrace. Natural light fills the room, complemented by a small table with fresh flowers and a map on the wall.

Home in Wynford Eagle

4.92 out of 5 average rating, 273 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.

Top guest favorite

A tall stone monument is prominently situated atop a grassy hill, surrounded by lush greenery. A weathered wooden signpost stands in the foreground, pointing in two directions. The sky features scattered clouds and clear blue sections, creating a bright outdoor scene.

Home in Dorset

4.97 out of 5 average rating, 142 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.

Guest favorite

The front of a charming stone cottage is displayed, featuring climbing greenery that softens the façade. A white picket fence encloses the small manicured garden, which includes a blooming red flower. Bright sunlight enhances the warm tones of the stonework and foliage.

Cottage in Martinstown

4.85 out of 5 average rating, 159 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.