Holiday houses in Winterbourne Steepleton

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Top-rated holiday rentals in Winterbourne Steepleton

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Guest favourite

Guest suite in Portesham

4.83 out of 5 average rating, 163 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.

19 – 26 June

$1,074 AUD total

Guest favourite

Cottage in Dorset

4.98 out of 5 average rating, 280 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. Min 2 night stay.

27 Feb – 6 Mar

$1,493 AUD total

Guest favourite

Hut in Piddlehinton

4.99 out of 5 average rating, 166 reviews

Kingfisher cabin in secluded Dorset woodland

In Middlemarsh not Piddlehinton. Reconnect with nature at this lovely secluded spot, surrounded by woodland and forest, this is the perfect getaway from busy city life. The cabin is located within an area of outstanding natural beauty with access to a great range of footpaths, and the Hunters Moon Inn a short walk away. It is also only a 30 minute drive to the Jurassic coast with beaches like Lulworth. There are a herd of friendly deer on site that you can be introduced too. We do not allow dogs

4 – 11 Apr

$1,168 AUD total

Guest favourite

Cottage in Dorset

4.97 out of 5 average rating, 537 reviews

Cute & Cosy Bothy Cottage, near Sherborne & Yeovil

The Bothy is a stylish detached cottage where you can share some Prosecco on your terrace or snuggle up beside a log fire Dating from the 1700's, our recently restored "boutique" stone cottage is in the rural historic Yetminster Conservation Area with a thatched pub, lovely local cafe & shop. It is next door to a quintessential English Heritage listed thatched cottage You are on the edge of the Dorset Area of Outstanding Natural Beauty and you have great access to the sea on the Jurassic Coast

21 – 28 Sept

$1,515 AUD total

Guest favourite

Barn in Dorset

4.98 out of 5 average rating, 117 reviews

West Dorset stylish rural bliss.

The barn is a beautifully converted stable. Open plan, cosy but stylish. Great music system, tv, free sat. On a farm but private. Under floor heating throughout and a well kitted kitchen. 1 lovely bedroom with bath and storage. Separate bathroom. Camp beds available for 2 : no older than 10ish. Cot, high chair etc available on request. A mile from the village with a good shop and local pub. Lovely walks and easy access to the Jurassic Coast. Happy to help and provide recommendations

8 – 15 Nov

$1,859 AUD total

Guest favourite

Guest suite in Dorset

4.92 out of 5 average rating, 125 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.

9 – 16 Dec

$1,084 AUD total

Guest favourite

Shepherd’s hut in Martinstown

4.96 out of 5 average rating, 140 reviews

Cosy Shepherds hut near Dorchester

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!

15 – 22 June

$1,102 AUD total

Guest favourite

Guesthouse in Dorchester

4.97 out of 5 average rating, 274 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.

27 Nov – 4 Dec

$918 AUD total

Guest favourite

Shepherd’s hut in Waddon

4.96 out of 5 average rating, 190 reviews

The Hide on the Vineyard with wood fired hot tub

'The Hide' is a romantic hideaway on an English Vineyard with your own Shepherd's Hut, Cabin, Shower room & Private Wood Fired Hot Tub for two Everything you see in the photos are for your own exclusive use - no neighbours, no sharing - your own corner of a beautiful vineyard! A perfect place to relax in a romantic setting for two With views across the valley and out to the sea Enjoy beautiful sunsets over the vines while you're soaking in your own private wood fired hot tub

31 Oct – 7 Nov

$2,268 AUD total

Guest favourite

Guest suite in Sydling Saint Nicholas

4.98 out of 5 average rating, 167 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.

3 – 10 Oct

$1,126 AUD total

Guest favourite

Guest suite in Long Bredy

4.92 out of 5 average rating, 140 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.

23 – 30 Mar

$1,311 AUD total

Guest favourite

Shepherd’s hut in West Bexington

4.97 out of 5 average rating, 346 reviews

The Seaside Shepherd’s Hut

Fall asleep to the sound of waves on shingle in this stunning, hand-crafted oak shepherd’s hut. In winter the Hut is cosy with double glazing, a wood burner plus radiator. In summer relax on the deck to enjoy glorious views of Lyme Bay in an AONB on the World Heritage Jurassic Coast. Nestling in the garden, Chesil Beach and the South West Coast Path are 30 seconds away down a private path. Watch magnificent sunsets over the bay and enjoy stargazing in our dark skies.

9 – 16 Apr

$1,442 AUD total