Holiday houses in Winterbourne Steepleton

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Winterbourne Steepleton

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Top Guest favourite
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 Yetminster
4.97 out of 5 average rating, 666 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 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, 107 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 exterior of the lodge features a modern, dark wooden facade with large glass doors that open into the main living area. A spacious patio area is surrounded by landscaped gardens, with decorative plants and seating arrangements for relaxation.
Home in Leigh
4.95 out of 5 average rating, 309 reviews

Luxurious rural retreat

The Lodge at Willen Farm is a beautiful single level converted barn on the outskirts of the quiet village of Leigh, just 4 miles from the town of Sherborne in Dorset. The Lodge provides the perfect location for a relaxing escape to the rural countryside, yet just 40 minutes from the fabulous Jurassic coastline. Spacious accommodation with two double bedrooms, one with en-suite shower/toilet and a separate bathroom. Contemporary style with an outside patio area. Parking and a small garden area.

Superhost
A cozy living room is furnished with a spacious sectional sofa facing a wall-mounted TV. Large glass doors offer sweeping views of the sky and surrounding area. Green plants add a natural touch, while a sleek wood-burning stove creates a focal point in the inviting space.
Condo in Westbourne
4.85 out of 5 average rating, 176 reviews

The Beach Hytte - Stunning Sea View Penthouse

Enjoy your perfect getaway in this award winning 2 bed penthouse apartment with 180 degree sea views in the heart of the tranquil Alum Chine area of Bournemouth just a few minutes walk from the beach. The property boasts two dining areas, one of which sits on the large balcony with views across Bournemouth beach and a bespoke wood burning stove for the winter nights. The open plan kitchen leads onto a cozy living room where you can enjoy Sky Glass TV entertainment through super fast WiFi.

Top 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
4.92 out of 5 average rating, 260 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 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, 113 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 favourite
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 Weymouth
4.94 out of 5 average rating, 232 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 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
4.79 out of 5 average rating, 191 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
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 Portesham
4.97 out of 5 average rating, 272 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

Guest favourite
A bright living room is illuminated by natural light from a large window, offering views of green fields. Comfortable seating is arranged around a wooden coffee table, with plush sofas and a decorative plant enhancing the welcoming space. A television set is positioned against the wall.
Bungalow in Weymouth
4.94 out of 5 average rating, 110 reviews

Bay View Luxury Stays - Southdown

This beautiful four bedroom property is located in the picturesque seaside town of Weymouth, offering breathtaking views over a stunning nature reserve , with its spacious rooms, comfortable furnishings and modern amenities, this property provides the perfect home away from home for families and friends, take in the sea air from the spacious garden patio area or admire the view from the many windows, the property is a short walk from the beach and charming shops.

Guest favourite
The exterior of The Parlour cottage is depicted, featuring a brick façade with large windows that allow natural light to fill the interior. A spacious gravel area surrounds the cottage, providing convenient access. The tranquil countryside can be glimpsed in the background under a clear blue sky.
Cottage in Buckland Newton
4.95 out of 5 average rating, 176 reviews

The Parlour, Duntish Mill Farm, EV Charging

The Parlour is a 3 double bedroom cottage which is part of Duntish Mill Farm that has recently been lovingly renovated. There is open plan living with vaulted ceilings and a cosy log burner. French doors that lead onto a large private patio area. Located in an AONB of Dorset, we are surrounded by plenty of stunning countryside centrally located between the historic towns of Sherbourne and Dorchester, which is also only a short drive away from the Jurassic Coast.

Top Guest favourite
Cottage in Martinstown
4.86 out of 5 average rating, 176 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.

Popular amenities for Winterbourne Steepleton holiday rentals