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Holiday Homes in Winterborne Stickland, Dorset

Self Catering Holiday Cottages in Winterborne Stickland, Dorset

Enjoy a self-catering escape in Winterborne Stickland, Dorset, with an array of charming holiday cottages, from pet-friendly remote hideaways to luxurious log cabins with hot tubs. Situated within the picturesque Dorset Area of Outstanding Natural Beauty and the Cranborne Chase, this quaint village is perfect for walkers, hikers, and cyclists looking to explore stunning landscapes. A short 20-mile drive brings you to the iconic Jurassic Coast for seaside adventures, while the nearby market town of Blandford Forum offers a vibrant local experience. Discover the perfect self-catering retreat in this idyllic setting.

Booking your holiday accommodation in Winterborne Stickland early is recommended for the best choice of holiday rentals.

Snowdrop Cottage, Dorset, England
Viewed 15× this week

Snowdrop Cottage

Dorchester, Dorset ~10 miles from Winterborne Stickland
Sleeps 4–9 4 Bedrooms 🐾 1 Dog
Next Available 29/08 to 04/09/2026
Facilities
WiFi Dishwasher Washing machine Games room Tennis Garden EV Charging Parking
Type of Holiday
1 dogs welcome
Weekly from £1,500 – £4,015
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Little Cheriton House, Somerset, England
Viewed 18× this week

Little Cheriton House

South Cheriton, Somerset ~16 miles from Winterborne Stickland
Sleeps 7–18 7 Bedrooms 🐾 1 Dog
Next Available 04/08 to 07/08/2026
Facilities
WiFi Open fire Microwave Dishwasher Washing machine Garden BBQ Parking
Type of Holiday
1 dogs welcome Hen Parties Group welcome
Weekly from £3,000 – £6,620
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Churchill House, Dorset, England
Viewed 16× this week

Churchill House

Minterne Magna, Dorset ~11 miles from Winterborne Stickland
Sleeps 8–17 8 Bedrooms 🐾 4 Dogs 🎉 Celebrations
Next Available 07/11 to 13/11/2026
Facilities
WiFi Microwave Dishwasher Washing machine BBQ Parking
Type of Holiday
4 dogs welcome Special celebrations Group welcome
Weekly from £3,100 – £7,200
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Cheesemans Cottage, Dorset, England
Viewed 19× this week

Cheesemans Cottage

Muckleford, Dorset ~14 miles from Winterborne Stickland
Sleeps 2–5 2 Bedrooms 🐾 3 Dogs
Next Available 04/08 to 07/08/2026
Facilities
WiFi Open fire Microwave Dishwasher Washing machine Garden Parking
Type of Holiday
3 dogs welcome
Weekly from £415 – £1,024
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Bucknowle Lodge, Dorset, England
Viewed 14× this week

Bucknowle Lodge

Church Knowle, Dorset ~16 miles from Winterborne Stickland
Sleeps 4–8 4 Bedrooms 🐾 2 Dogs
Next Available 24/08 to 28/08/2026
Facilities
WiFi Open fire Coffee machine Microwave Dishwasher Washing machine Parking
Type of Holiday
2 dogs welcome
Weekly from £1,100 – £2,995
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Silvermere, Dorset, England
Viewed 17× this week

Silvermere

Higher Woodsford, Dorset ~11 miles from Winterborne Stickland
Sleeps 4–10 4 Bedrooms 🚫 No Dogs
Next Available 04/08 to 07/08/2026
Facilities
WiFi Open fire Coffee machine Microwave Dishwasher Washing machine Pool Sauna
Type of Holiday
No dogs allowed
Weekly from £1,500 – £4,075
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The Lookout, Dorset, England
Viewed 15× this week

The Lookout

Abbotsbury, Dorset ~11 miles from Winterborne Stickland
Sleeps 4–8 4 Bedrooms 🚫 No Dogs
Next Available 01/09 to 18/09/2026
Facilities
WiFi Open fire Microwave Dishwasher Washing machine Tennis EV Charging Parking
Type of Holiday
No dogs allowed
Weekly from £1,530 – £4,300
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White Sands, Dorset, England
Viewed 18× this week

White Sands

Swanage, Dorset ~19 miles from Winterborne Stickland
Sleeps 4–7 4 Bedrooms 🐾 2 Dogs
Next Available 03/10 to 24/10/2026
Facilities
WiFi Microwave Dishwasher Washing machine Parking
Type of Holiday
2 dogs welcome
Weekly from £1,285 – £3,430
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Kings House, Dorset, England
Viewed 19× this week

Kings House

Minterne Parva, Dorset ~11 miles from Winterborne Stickland
Sleeps 2–4 2 Bedrooms 🐾 2 Dogs
Next Available 01/09 to 30/09/2026
Facilities
Microwave Dishwasher Pool Tennis Garden BBQ Parking
Type of Holiday
2 dogs welcome
Weekly from £850 – £1,495
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The Fishing Lodge, Dorset, England
Viewed 26× this week

The Fishing Lodge

Sydling St Nicholas, Dorset ~14 miles from Winterborne Stickland
Sleeps 1–4 2 Bedrooms 🚫 No Dogs 🎉 Celebrations
Next Available 04/08 to 14/08/2026
Facilities
WiFi Open fire Microwave Dishwasher Washing machine Garden BBQ Parking
Type of Holiday
No dogs allowed Special celebrations
Weekly from £800 – £1,800
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Private Rural Lodge, Wrackleford Estate, Dorset, England
Viewed 14× this week

Private Rural Lodge, Wrackleford Estate

Stratton, Dorset ~13 miles from Winterborne Stickland
Sleeps 4–8 4 Bedrooms 🚫 No Dogs 🎉 Celebrations
Next Available 04/08 to 07/08/2026
Facilities
WiFi Woodburner Open fire Coffee machine Microwave Dishwasher Washing machine Games room
Type of Holiday
No dogs allowed Special celebrations Corporate events
Weekly from £1,100 – £4,000
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Langford Valley Barn, Dorset, England
Viewed 15× this week

Langford Valley Barn

Dorchester, Dorset ~13 miles from Winterborne Stickland
Sleeps 4–8 4 Bedrooms 🚫 No Dogs 🎉 Celebrations
Next Available 04/08 to 07/08/2026
Facilities
WiFi Woodburner Coffee machine Microwave Dishwasher Washing machine Games room Garden
Type of Holiday
No dogs allowed Special celebrations Corporate events
Weekly from £1,200 – £3,000
View


Cottages, Apartments & Lodges in Winterborne Stickland, Dorset, England

RuralHomeStays.Com features holiday home(s) within or close to Winterborne Stickland, enjoy browsing through the available options. We hope you find the perfect holiday house for you in Winterborne Stickland, Dorset.


Winterborne Stickland Self-Catering Holidays

Looking for a self-catering holiday cottage in Winterborne Stickland? Discover a brilliant selection of holiday homes, cabins, and chalets in or around the village of Winterborne Stickland in Dorset.

What Winterborne Stickland Offers for Cottage Breaks

Charming and secluded country village, ideal for a touring holiday of Dorset or for true escapists. Nestled in the middle of the Dorset Area of Outstanding Natural Beauty and the Cranborne Chase Area of Outstanding Natural Beauty, making Winterborne Stickland a great location for keen walkers, hikers, and cyclists.

Nearby Attractions & Activities

Winterborne Stickland is around a 20-mile drive from the Jurassic Coast, perfect for a seaside day trip. Less than 5 miles from the bustling market town of Blandford Forum, a favourite for tourists!

Accommodation Options in Winterborne Stickland

Whether you’re looking for a pet-friendly remote country cottage, a renovated barn, or a log cabin with a hot tub, we hope you find your perfect self-catering holiday in or near Winterborne Stickland in Dorset.

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