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Holiday Homes in Gillingham, Dorset

Self Catering Holiday Cottages in Gillingham, Dorset

Experience a delightful self-catering escape in Gillingham, Dorset, with a range of holiday cottages, lodges, and chalets to choose from. Nestled on the edge of the Cranborne Chase Area of Outstanding Natural Beauty, this charming town is perfect for nature lovers and those seeking picturesque views. Easily accessible by train, Gillingham offers ample dining options for a relaxing evening. Ideal for day trips, it’s just 20 miles from Yeovil and under 25 miles from the historic city of Wells. Whether a romantic cottage, a spacious manor, or a pet-friendly lodge, find your perfect getaway in Gillingham.

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

Portman House
Pylle, Somerset Around 15 miles from Gillingham
Portman House, Somerset, England Viewed 26 times in last week.
Sleeps 8 - 16, 8 Bedroom
Weekly price: £ 4175 - £ 7265
Next Available: 12/01 to 16/01/2026
Living & Leisure Facilities: Open fire coffee machine Microwave Dishwasher Games room Sauna Garden
Type of Holiday: 2 dogs welcome Group welcome
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Lower Hedge Farm
Shepton Mallet, Somerset Around 14 miles from Gillingham
Lower Hedge Farm , Somerset, England Viewed 26 times in last week.
Sleeps 5 - 12, 5 Bedroom
Weekly price: £ 2500 - £ 4380
Next Available: 11/01 to 13/02/2026
Living & Leisure Facilities: woodburner Open fire Microwave Dishwasher Washing machine Games room Garden
Type of Holiday: 2 dogs welcome Group welcome Weddings
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The Cider Barn
West Pennard, Somerset Around 17 miles from Gillingham
The Cider Barn, Somerset, England Viewed 19 times in last week.
no booking fee
Sleeps 6 - 12, 6 Bedroom
Weekly price: £ 3010 - £ 5415
Next Available: 12/01 to 15/01/2026
Living & Leisure Facilities: Microwave Dishwasher Washing machine Garden BBQ free wifi
Type of Holiday: 2 dogs welcome Special celebrations Hen Parties Group welcome
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Woodlands Farmhouse
Glastonbury, Somerset Around 17 miles from Gillingham
Woodlands Farmhouse , Somerset, England Viewed 30 times in last week.
Sleeps 7 - 14, 7 Bedroom
Weekly price: £ 3350 - £ 5735
Next Available: 11/01 to 16/01/2026
Living & Leisure Facilities: woodburner Open fire Microwave Dishwasher Washing machine Own swimming pool Games room
Type of Holiday: 2 dogs welcome Group welcome Weddings
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Swallow's Orchard
West Bradley, Somerset Around 17 miles from Gillingham
Swallow's Orchard, Somerset, England Viewed 24 times in last week.
Sleeps 1 - 6, 3 Bedroom
Weekly price: £ 1400 - £ 3165
Next Available: 11/01 to 16/01/2026
Living & Leisure Facilities: woodburner Microwave Dishwasher Washing machine Own swimming pool Sauna Garden
Type of Holiday: 2 dogs welcome Corporate events
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Little Cheriton House
South Cheriton, Somerset Around 7 miles from Gillingham
Little Cheriton House, Somerset, England Viewed 17 times in last week.
Sleeps 7 - 18, 7 Bedroom
Weekly price: £ 3000 - £ 6555
Next Available: 11/01 to 16/01/2026
Living & Leisure Facilities: Open fire Microwave Dishwasher Washing machine Garden BBQ free wifi
Type of Holiday: 1 dogs welcome Hen Parties Group welcome
View
The Old Milking Parlour
Wells, Somerset Around 17 miles from Gillingham
The Old Milking Parlour, Somerset, England Viewed 20 times in last week.
Sleeps 1 - 4, 2 Bedroom
Weekly price: £ 395 - £ 795
Sorry this property has not provided availability and detailed pricing information.
Living & Leisure Facilities: woodburner Microwave Dishwasher Washing machine Garden free wifi
Type of Holiday: No dogs allowed
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Cottages, Apartments & Lodges in Gillingham, Dorset, England

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

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Holiday Cottages in Gillingham

Looking for a holiday cottage in Gillingham? Find a fabulous selection of holiday homes, lodges and chalets in or around the town of Gillingham in Dorset.

What Does Gillingham Offer for Self-Catering Holidays?

Charming country town situated on the edge of the Cranborne Chase Area of Outstanding Natural Beauty, ideal for those who like to walk or for those who appreciate a nice view. Gillingham has its own train station and plenty of places to eat and drink, a perfect way to spend an evening on holiday. The town is around 20 miles from the popular market town of Yeovil. Gillingham is less than 25 miles from the cathedral city of Wells, a fun and historical day out.

Self-Catering Breaks in Gillingham

Whether you are looking for a romantic country-chic cottage for yourself and your sweetheart, an impressive country manor for your hen party or a pet-friendly pine lodge with a hot tub, we hope you find your dream self-catered holiday in or around the town of Gillingham in Dorset.

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