Gillingham Holiday Cottages

19 holiday rentals
Gillingham 14 miles away

Apple Cottage

, Pylle, Somerset, South West England, England
Online Booking Available
Viewed 22 times recently.
Price from £740
Next available 04 October to 09 October 23
0 ( reviews)
sleeps  4 sleeps 4
2 bedrooms 2 bedrooms
2 bathrooms 2 bathrooms
2 dogs welcome  2 dogs
family friendly family friendly

2 bedroom dog-friendly holiday house

2 bedroom dog-friendly holiday house in Somerset with hot tub spa bath, log burner and garden.

High quality boutique style holiday home set in a peaceful rural setting with a tranquil garden and private hot tub

Facilities & Features: Gold Award Winning CottageTVFree WifiOutdoor Hot TubEnclosed Garden
5 star rated
Best for: Family holidays, Pets Welcome Breaks
Gillingham 13 miles away

4 Bridge Cottages

, Marston Magna, Somerset, South West England, England
Online Booking Available
Viewed 14 times recently.
Price from £390
Next available 05 October to 16 December 23
0 ( reviews)
no booking fee
sleeps  4 sleeps 4
2 bedrooms 2 bedrooms
1 bathrooms 1 bathroom
no dogs allowed No pets
family friendly family friendly

2 bedroom family-friendly rental

2 bedroom family-friendly rental in Somerset with recreation room and garden.

Two bedroom family holiday cottage with a private south facing garden and country views located in a rural village in Somerset close to Glastonbury Tor, available for short breaks and longer stays

Facilities & Features: TVFree WifiGames roomEnclosed Garden
Gillingham 12 miles away

Victoria Albert at The Victorian Barn

, Blandford Forum, Dorset, South West England, England
Online Booking Available
Viewed 75 times recently.
Price from £1600
Next available 26 September to 06 October 23
0 ( reviews)
no booking fee
sleeps  16 sleeps 16
5 bedrooms 5 bedrooms
6 bathrooms 6 bathrooms
no dogs allowed No pets
family friendly family friendly

5 bedroom cottage for families

5 bedroom cottage for families in Dorset with hot tub spa bath, swimming pool, jacuzzi, sauna room, games room and garden.

Sleeps 16 no pets holiday home in Dorset AONB, just half an hour’s drive from the Jurassic coast, with private hot tub and access to excellent onsite leisure facilities included a heated indoor pool, a sauna, games room, kids play areas and coarse fishing lakes

Facilities & Features: Gold Award Winning CottageDigital TVFree WifiGames roomOutdoor Hot TubSaunaHeated poolGarden
Gillingham 17 miles away

Swallow's Orchard

, West Bradley, Somerset, South West England, England
Online Booking Available
Viewed 40 times recently.
Price from £1500
Next available 06 October to 09 October 23
0 ( reviews)
sleeps  6 sleeps 6
3 bedrooms 3 bedrooms
3 bathrooms 3 bathrooms
2 dogs welcome  2 dogs
family friendly family friendly

3 bedroom dog-friendly holiday rental

3 bedroom dog-friendly holiday rental in Somerset with hot tub, swimming bath, sauna, woodburning stove and garden.

A unique and contemporary detached holiday home nestled next to an old apple orchard with a truly tranquil setting in Somerset amidst nature and countryside with a private hot tub and shared use of an indoor pool, hot tub, sauna and gym

Facilities & Features: Gold Award Winning CottageTVFree WifiOutdoor Hot TubSaunaHeated poolEnclosed Garden
5 star rated
Best for: Families, Dog-Friendly Holidays
Gillingham 17 miles away

The Old Milking Parlour

, Wells, Somerset, South West England, England
Online Booking Available
Viewed 24 times recently.
Price from £700
Next available 25 September to 20 October 23
0 ( reviews)
no booking fee
sleeps  4 sleeps 4
2 bedrooms 2 bedrooms
2 bathrooms 2 bathrooms
no dogs allowed No pets
family friendly family friendly

2 bedroom family-friendly cottage

2 bedroom family-friendly cottage in Somerset with woodburner and garden.

With a gold award, a 4 star rating and views over the Mendip Hills and open countryside, the Old Milking Parlour has plenty to recommend it

Facilities & Features: Gold Award Winning CottageDigital TVFree WifiGarden
4 star rated
Gillingham 14 miles away

Lower Hedge Farm

, Shepton Mallet, Somerset, South West England, England
Online Booking Available
Viewed 54 times recently.
Price from £3230
Next available 25 September to 20 October 23
0 ( reviews)
sleeps  12 sleeps 12
5 bedrooms 5 bedrooms
4 bathrooms 4 bathrooms
2 dogs welcome  2 dogs
family friendly family friendly

5 bedroom dog-friendly holiday cottage

5 bedroom dog-friendly holiday cottage in Somerset with hot tub, recreation room, open fire and garden.

A stunning large luxurious holiday house boasting unspoilt views over the open countryside with a private hot tub and games room complete with pool table and table tennis for fun times

Facilities & Features: TVGames roomOutdoor Hot TubEnclosed Garden
5 star rated
Best for: Family-friendly, Dogs Welcome Breaks
Gillingham 17 miles away

The Cider Barn

, West Pennard, Somerset, South West England, England
Family-Friendly
Viewed 31 times recently.
Price from £2925
Next available 12 October to 16 October 23
0 ( reviews)
no booking fee
sleeps  12 sleeps 12
6 bedrooms 6 bedrooms
6 bathrooms 6 bathrooms
2 dogs welcome  2 dogs
family friendly family friendly

6 bedroom pet-friendly holiday rental

6 bedroom pet-friendly holiday rental in Somerset with garden.

High quality 6 bedroom, sleeps 12 pet-friendly barn conversion (all en-suite bedrooms) in rural Somerset, close to Glastonbury, and boasting a private bubbly outdoor hot tub and shared access to a swimming pool and sauna

Facilities & Features: TVFree WifiHeated poolEnclosed Garden
Best for: Group Holidays, Hen parties, Special celebrations, Families, Dog-Friendly Holidays
Gillingham 16 miles away

Woodlands Farmhouse

, Glastonbury, Somerset, South West England, England
Online Booking Available
Viewed 80 times recently.
Price from £3410
Next available 02 October to 06 October 23
0 ( reviews)
sleeps  14 sleeps 14
7 bedrooms 7 bedrooms
6 bathrooms 6 bathrooms
2 dogs welcome  2 dogs
family friendly family friendly

7 bedroom dog-friendly cottage

7 bedroom dog-friendly cottage in Somerset with hot tub spa bath, swimming pool, sauna room, games room, woodburner, real fire and garden.

A unique and historic grade II listed 17th century farmhouse set in 100 acres of rolling countryside, luxuriously renovated yet retaining many of it’s original features such as the stunning inglenook fireplace, with a cinema room and shared access to a spa on site with an indoor swimming pool, sauna and gym, this is a wonderful holiday home

Facilities & Features: Gold Award Winning CottageTVFree WifiGames roomOutdoor Hot TubSaunaHeated poolEnclosed Garden
5 star rated
Best for: Family holidays, Dog-Friendly Holidays
Gillingham 12 miles away

The Old Stables Holiday Barn

, Winterborne Stickland, Dorset, South West England, England
Online Booking Available
Viewed 9 times recently.
Price from £1042
Next available 25 September to 28 September 23
0 ( reviews)
sleeps  6 sleeps 6
3 bedrooms 3 bedrooms
2 bathrooms 2 bathrooms
1 dog welcome  1 dog
family friendly family friendly

3 bedroom pet-friendly cottage

3 bedroom pet-friendly cottage in Dorset with games den, log burner, real fireplace and garden.

Family-friendly and dog-friendly barn conversion with modern interior, situated within a small development on a working farm, ideal for rural retreat breaks and within reach of the Jurassic Coast

Facilities & Features: TVFree WifiGames roomGarden
5 star rated
Best for: Families, Pets Welcome Breaks
Gillingham 17 miles away

Shepherd's Hut Barn, rural Dorset

, Winterborne Whitechurch, Dorset, South West England, England
Online Booking Available
Viewed 10 times recently.
Price from £1426
Next available 03 November to 18 November 23
0 ( reviews)
sleeps  6 sleeps 6
3 bedrooms 3 bedrooms
2 bathrooms 2 bathrooms
2 dogs welcome  2 dogs
family friendly family friendly

3 bedroom dog-friendly holiday cottage

3 bedroom dog-friendly holiday cottage in Dorset with log burner and garden.

Want to stay somewhere with tranquil rural views over fields and pastures where you can relax and unwind in Dorset? This 3 bedroom family-friendly and dog-friendly ban could be perfect, close to Thomas Hardy's Country and within reach of Dorset's Jurassic Coast for day trips

Facilities & Features: TVFree WifiGarden
5 star rated
Best for: Family-friendly, Dogs Welcome Breaks
Gillingham 6 miles away

Ryecross Rural Retreat near Shaftesbury

, Shaftesbury, Dorset, South West England, England
Online Booking Available
Viewed 7 times recently.
Price from £489
Next available 14 October to 04 November 23
0 ( reviews)
sleeps  4 sleeps 4
2 bedrooms 2 bedrooms
1 bathrooms 1 bathroom
no dogs allowed No pets
family friendly family friendly

2 bedroom family holiday house

2 bedroom family holiday house in Dorset with garden.

Get away from it all with a stay at this idyllic rural retreat near the attractive hillside town of Shaftesbury in Dorset

Facilities & Features: TVFree WifiGarden
3 star rated
Best for: Family holidays, No Pets Breaks
Gillingham 4 miles away

Cider Barn Romantic Retreat, Cranborne Chase AONB

, West Knoyle, Wiltshire, South West England, England
Online Booking Available
Viewed 9 times recently.
Price from £448
Next available 24 October to 03 November 23
0 ( reviews)
sleeps  2 sleeps 2
1 bedrooms 1 bedroom
1 bathrooms 1 bathroom
1 dog welcome  1 dog

1 bedroom dog-friendly holiday cottage

1 bedroom dog-friendly holiday cottage in Wiltshire with garden.

Idyllic rural retreat which with its king-size bed is ideal for two, this studio property is complete with a beautiful interior and a lovely countryside location and is situated near to the West Wiltshire Downlands

Facilities & Features: TVFree WifiGarden
5 star rated
Best for: Couples, Dog-Friendly Breaks
Gillingham 15 miles away

Apple Tree Cottage

, Blandford Forum, Dorset, South West England, England
Price from £1721
Next available 01 October to 06 October 23
0 ( reviews)
sleeps  10 sleeps 10
5 bedrooms 5 bedrooms
3 bathrooms 3 bathrooms
no dogs allowed No pets
family friendly family friendly

5 bedroom family-friendly cottage

5 bedroom family-friendly cottage in Dorset with hot tub spa bath, woodburner and garden.

Pretty 5 bedroom thatched country cottage, near Blandford Forum, with warm bubbly outdoor hot tub in garden

Facilities & Features: TVFree WifiOutdoor Hot TubEnclosed Garden
5 star rated
Best for: Families, Pet Free Breaks
Gillingham 16 miles away

The Bolt Hole Romantic Retreat

, Shepton Mallet, Somerset, South West England, England
Online Booking Available
Viewed 7 times recently.
Price from £788
Next available 01 January to 24 September 24
0 ( reviews)
sleeps  2 sleeps 2
1 bedrooms 1 bedroom
1 bathrooms 1 bathroom
1 dog welcome  1 dog

1 bedroom pet-friendly cottage

1 bedroom pet-friendly cottage in Somerset with woodburning stove, open fireplace and garden.

Quirky pet-friendly romantic retreat near Wells

Facilities & Features: TVFree WifiGarden
4 star rated
Best for: Romantic Breaks, Pets Welcome Breaks
Gillingham 7 miles away

Little Cheriton House

, South Cheriton, Somerset, South West England, England
Family-Friendly
Viewed 23 times recently.
Price from £3610
Next available 25 September to 06 October 23
0 ( reviews)
sleeps  18 sleeps 18
7 bedrooms 7 bedrooms
5 bathrooms 5 bathrooms
no dogs allowed No pets
family friendly family friendly

7 bedroom pet-friendly holiday rental

7 bedroom pet-friendly holiday rental in Somerset with hot tub spa bath, real fire and garden.

Stylish and impressive 7 bedroom manor house with stunning country views, private outdoor hot tub and spacious elegant accommodation, half an hour's drive from Yeovil

Facilities & Features: TVFree WifiOutdoor Hot TubGarden
Best for: Families, Pet Free Breaks
* Price quoted is not inclusive of any applicable booking fees or local charges.

Gillingham is the most northerly town in Dorset and is an excellent base for a self-catering holiday with easy road access to towns in Dorset, Devon and Salisbury Plain. It sits conveniently between the A303 and A30, major roadways through the West Country that merge north of Honiton in Devon. Gillingham is an attractive town, surrounded by quaint Dorset villages with some beautiful countryside and is the hub for this pretty part of Dorset. The town remains mainly unspoilt and has attractive streets and some historic buildings dating as far back as the 15th century. Whether you are looking to take a self-catering break in Gillingham itself or a country cottage holiday in the nearby countryside, this is a picturesque part of the West Country with lots to offer visitors.


Hints and Tips on Cottage Holidays in Gillingham

It has had its share of visitors over the centuries, the Romans were in the district, one in the form of a skeleton still resides at the local museum. Gillingham was the site of a royal hunting lodge during the middle ages that was said to have been frequented by King John, and Kings Henry I, II, and III. In Hardy’s novels Gillingham is portrayed by Leddington and John Constable was a regular visitor, producing some fine drawings and paintings of the town. One of the old bridge is displayed in the Tate Gallery. The church of St. Mary the Virgin was restored in Victorian Times but an Anglo-Saxon stone bearing what could be an interlaced cross can be seen in the church as evidence of very early Christianity in the area. Today there are in excess of 70 shops in the town besides pubs and restaurants, so you are well catered for during your self-catering stay.

Just five miles from Gillingham is the larger town of Shaftesbury. Whilst on your cottage holiday you can walk up the cobbled Gold Hill just like the lad with his baker’s bike in the famous Hovis commercial, while to the north a great day out is to be had for families with a safari at Longleat Safari Park. Railway enthusiasts don’t have to travel far from Gillingham as the Gartell Light Railway can be found off the A303 at Templecombe. A trip out to Salisbury Plain and Stonehenge is a memorable experience, and although much of the area is one huge MOD training ground there are paths and routes for walkers to enjoy legally and safely. The cathedral town of Salisbury is a beautiful place recommended for a visit and as it is on the railway line from Gillingham, you can leave the car behind and stay free from parking charges whilst you explore. You can even take a bus from the bus station for an organised guided tour of Stonehenge if you wish.

Whether you plan to discover this part of the West Country with your family, friends or partner, you will find this a beautiful part of Dorset with lots to offer. When it comes to finding somewhere to stay choose from family cottages, large cottages and romantic cottages, we hope you find an ideal place to stay.

Whether you choose to book a holiday cottage in Gillingham, an apartment, a lodge or another type of self-catering holiday accommodation, we hope you have your best holiday yet in Dorset.

Frequently Asked Questions about Gillingham

The best places to stay depend on your preferences, interests and the type of accommodation that best suits you. Country Cottages Online features a great selection of good quality rentals.
See our selection of pet-friendly rentals in Gillingham, or use the filters to refine your search.
See our selection of lodges and cabins in Gillingham, Dorset.
Read the description of Gillingham to find out ideas and tips on the best things to see and do. Also see our area guides for more information on what Dorset has to offer for holidaymakers.

Gillingham Holiday Rental Searches