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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.

Waterlake Cottage, Orcheston, nr Stonehenge, Wiltshire, England
Viewed 15× this week No booking fee

Waterlake Cottage, Orcheston, nr Stonehenge

Stonehenge, Wiltshire ~20 miles from Gillingham
Sleeps 2–4 2 Bedrooms 🚫 No Dogs
Next Available 31/08 to 17/09/2026
Facilities
WiFi Open fire Coffee machine Microwave Washing machine Garden BBQ Parking
Type of Holiday
No dogs allowed
Weekly from £650 – £650
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Portman House, Somerset, England
Viewed 16× this week

Portman House

Pylle, Somerset ~15 miles from Gillingham
Sleeps 8–16 8 Bedrooms 🐾 2 Dogs
Next Available 04/08 to 07/08/2026
Facilities
Open fire Coffee machine Microwave Dishwasher Games room Sauna Garden
Type of Holiday
2 dogs welcome Group welcome
Weekly from £4,175 – £7,480
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Woodlands Farmhouse , Somerset, England
Viewed 18× this week

Woodlands Farmhouse

Glastonbury, Somerset ~17 miles from Gillingham
Sleeps 7–14 7 Bedrooms 🐾 2 Dogs
Next Available 23/08 to 26/08/2026
Facilities
WiFi Woodburner Open fire Microwave Dishwasher Washing machine Pool Games room
Type of Holiday
2 dogs welcome Group welcome Weddings
Weekly from £3,350 – £5,850
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Lower Hedge Farm , Somerset, England
Viewed 17× this week

Lower Hedge Farm

Shepton Mallet, Somerset ~14 miles from Gillingham
Sleeps 5–12 5 Bedrooms 🐾 2 Dogs
Next Available 04/08 to 07/08/2026
Facilities
WiFi Woodburner Open fire Microwave Dishwasher Washing machine Games room Garden
Type of Holiday
2 dogs welcome Group welcome Weddings
Weekly from £2,500 – £4,425
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Swallow's Orchard, Somerset, England
Viewed 15× this week

Swallow's Orchard

West Bradley, Somerset ~17 miles from Gillingham
Sleeps 1–6 3 Bedrooms 🐾 2 Dogs
Next Available 07/08 to 17/08/2026
Facilities
WiFi Woodburner Microwave Dishwasher Washing machine Pool Sauna Garden
Type of Holiday
2 dogs welcome Corporate events
Weekly from £1,400 – £3,310
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Kings House, Dorset, England
Viewed 19× this week

Kings House

Minterne Parva, Dorset ~17 miles from Gillingham
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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Little Cheriton House, Somerset, England
Viewed 18× this week

Little Cheriton House

South Cheriton, Somerset ~7 miles from Gillingham
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 ~17 miles from Gillingham
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
View
Apple Cottage Hot Tub Retreat, Somerset, England
Viewed 20× this week

Apple Cottage Hot Tub Retreat

Pylle, Somerset ~14 miles from Gillingham
Sleeps 1–4 2 Bedrooms 🐾 2 Dogs
Next Available 18/08 to 26/08/2026
Facilities
WiFi Woodburner Microwave Dishwasher Washing machine Balcony Garden Parking
Type of Holiday
2 dogs welcome
Weekly from £740 – £1,600
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The Cider Barn, Somerset, England
Viewed 18× this week No booking fee

The Cider Barn

West Pennard, Somerset ~17 miles from Gillingham
Sleeps 6–12 6 Bedrooms 🐾 2 Dogs 🎉 Celebrations
Next Available 09/08 to 17/08/2026
Facilities
WiFi Microwave Dishwasher Washing machine Garden BBQ Parking
Type of Holiday
2 dogs welcome Special celebrations Hen Parties Group welcome
Weekly from £3,010 – £5,855
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The Old Milking Parlour, Somerset, England
Viewed 15× this week

The Old Milking Parlour

Wells, Somerset ~17 miles from Gillingham
Sleeps 1–4 2 Bedrooms 🐾 1 Dog
Facilities
WiFi Woodburner Microwave Dishwasher Washing machine Garden BBQ Parking
Type of Holiday
1 dogs welcome
Weekly from £395 – £795
View


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.


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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