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Maidstone Holiday Cottages

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Your Maidstone, Kent search returned 18 cottages

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  • Sleeps10
  • Bedrooms5
  • PetsNo
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This historic 14th century medieval hall is now luxury accommodation within the Leeds Castle Estate in Kent. En-suite. Enclosed garden. Grand interior and furnishings. Maidstone 6.9 miles; Cantebury 23.2 miles. (Ref. 1002747)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £4230

  • Sleeps10
  • Bedrooms5
  • PetsNo

    4.4

    Good

  • Sykes rating

This wonderful cottage rests in the village of Broomfield, in the Maidstone district of Kent. Woodburning stove. County views. Maidstone 5.7 miles. (Ref. 1022847)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £1453

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

This terraced property is located in Broomfield near the village of Hollingbourne in Kent. Large garden. Woodland setting. Maidstone 5.7 miles; Rochester 13.1 miles; Canterbury 23.2 miles. (Ref. 1002756)

  • Wi-fi
  • Off-road parking

7 nights from £664

7 nights from £985

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

This charming annexe rests on the owners' grounds in a peaceful location in East Farleigh near Maidstone, Kent. Designated parking. Garden. Close to amenities. Rochester 11.5 miles; Canterbury 31.1 miles (Ref. 1125491)

  • Wi-fi
  • Off-road parking
  • Washing machine
  • Baby-friendly

7 nights from £539

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

This superb barn conversion rests in the small village of Broomfield, in the Maidstone district of Kent. Electric woodburning stove. Private parking. Maidstone 5.7 miles. (Ref. 1002750)

  • Wi-fi
  • Off-road parking
  • Washing machine

7 nights from £852

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A homely ground-floor cottage tucked away on the rural outskirts of West Peckham near Hadlow, Kent. Underfloor heating. Private garden. WiFi. Tonbridge 5.8 miles; Maidstone 9.1 miles; Royal Tunbridge Wells 10.8 miles. (Ref. 1068731)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £732

  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A lovely three-bedroom first-floor apartment resting in Kingswood, near Langley in Kent. Open-plan. Smart TVs. Off-road parking. Private garden. Otham 3.4 miles; Maidstone 6.1 miles; Kent Downs AONB 19 miles. (Ref. 1077629)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £853

  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

A well-presented, period cottage nestled on the edge of the Leeds Castle Estate, Kent. Feature fireplace. Garden. Off-road parking. Maidstone 6.6 miles; Rochester 14.1 miles. (Ref. 1103881)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £860

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Delightful, detached lodge, Elevated location with wonderful views, Forest to the rear and a haven for wildlife, ideally suited to animal lovers, Perfect romantic retreat, Ideal for walking, touring and relaxing, WiFi, Sevenoaks 11.5 miles. (Ref. 946987)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £399

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

This wonderful ground-floor studio apartment rests on the outskirts of Paddock Wood, Kent. Pet-friendly. Off-road parking. Open-plan. Maidstone 8.7 miles; Tonbridge 9 miles; Royal Tunbridge Wells 9.9 miles. (Ref. 1080904)

  • Off-road parking
  • Ground floor bedroom
  • Baby-friendly

7 nights from £372

  • Sleeps4
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

This delightful holiday property rests in Paddock Wood, Kent. Countryside views. Woodburning stove. Large, lawned area. Tonbridge 6.2 miles; Royal Tunbridge Wells 7.2 miles; Maidstone 11.6 miles (Ref. 1127384)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £428

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Lovely, detached bungalow in owner's grounds overlooking orchards. Spacious, modern and well equipped. Close to fishing lakes. Superb base for exploring Kent and Sussex. Yalding 2 miles. (Ref. 917453)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £319

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

The Milking Parlour is a characterful, two-bedroom cottage residing in Frittenden near Cranbrook, Kent. Near the High Weald AONB. Woodburning stove. Goudhurst 8.3 miles; Tenterden 8.4 miles; Maidstone 12.9 miles. (Ref. 1138166)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from £533

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A ground floor annexe situated near the hamlet of Oad Street near Sittingbourne in Kent. Pet-friendly. Garden with patio area. Sittingbourne 1.7 miles; Rochester 10.2 miles; Tunbridge Wells 31.2 miles. (Ref. 960985)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £349

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Cherry Orchard Farm, a lovely barn conversion resting just outside Wateringbury, Kent. Single-storey. Private garden. Open-plan. Private parking. Maidstone 4.8 miles; Tonbridge 10.9 miles; High Weald National Landscape 17.2 miles. (Ref. 1148600)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £499

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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

The Old Stables is a charming annexe, within extensive grounds boasting a lake, meadow, fields, and orchards, in the quaint village of Headcorn, Kent. Staplehurst 4.2 miles; Maidstone 9.2 miles; High Weald National Landscape 14.2 miles. (Ref. 1162125)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom

7 nights from £380

Last booked yesterday
See more details
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A cosy, comfortable barn conversion in a rural setting near Lenham. All ground floor. Beams. Excellent location for walking and cycling. Lenham 3 miles. (Ref. 27285)

  • Off-road parking
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from £356

These wonderful holiday cottages in Maidstone are the perfect base to experience the best of Kent’s rich heritage and beautiful landscapes. Nestled in the heart of the county, Maidstone offers a variety of attractions, from the stunning Leeds Castle to the scenic Kent Downs.

Why Holiday Cottages in Maidstone 

These holiday cottages in Maidstone are perfect for families, couples and groups of friends looking to create lasting memories. Each Maidstone cottage offers the perfect base for those looking to explore the beauty of Kent. 

Set in the heart of Maidstone, you’re just a stone’s throw away from the vibrant town, which boasts a rich history and an array of amenities, including shops, restaurants, and entertainment options, ensuring that everything you need is right at your doorstep. Maidstone’s central location in the county itself puts you in a great place to explore this fantastic region, from the White Cliffs of Dover to visiting the only desert in the UK, Dungeness.

From the nearby Leeds Castle to Dover Castle, there is so much history to explore. Whether you’re interested in history or nature, holiday cottages in Maidstone provide the perfect setting for an unforgettable getaway in the Garden of England. 

If you’re looking for more inspiration on what to do during your stay at a holiday cottage in Maidstone, check out our Kent Travel Guide

Places to Visit from Cottages in Maidstone 

Staying in a cottage in Maidstone opens up a wealth of exciting places to explore throughout Kent. One of the must-visit attractions is Leeds Castle, located just a short drive away. This stunning fortress is surrounded by beautiful gardens and parkland, perfect for leisurely strolls. Soak up the history of this historic structure, if you time it well they also have various events held throughout the year! 

These cottages in Maidstone are also within reach of the iconic White Cliffs of Dover. With fantastic views out to sea and the chance to see France on a good day, this area is a must-visit. Choosing accommodation in Maidstone is perfect for those seeking a coastal escape, as the seaside towns of Herne Bay, Margate, and Ramsgate are all within reach. 

Look forward to completing the traditional seaside bucket list, by heading to adventure golf courses, amusement parks and enjoying a takeaway fish and chips with a candy floss treat to end the day. There are so many great beaches along the Kent coastline to explore too; you’ll be spoilt for choice! 

During your holiday to Maidstone, be sure to visit Dungeness, Britain's only desert, where you can explore RSPB Dungeness, a haven for keen walkers and wildlife lovers.

Other destinations within reach of accommodation in Maidstone 

Ashford 

Canterbury 

Ramsgate

Royal Tunbridge Wells

Types of Kent Holidays 

Begin your next adventure today by booking one of these delightful holiday cottages in Maidstone! 

If you’re still looking for your perfect getaway in Kent, there are plenty of other options. Secure your location by the sea by booking one of these coastal cottages in Kent. You can also experience something unique with these glamping pods in Kent

Don’t worry if you’re planning a spontaneous trip, you can also choose from these last-minute cottages in Kent or these short breaks in Kent. If you’re looking for a spot of luxury then you can choose from these cottages in Kent with hot tubs.  You can even choose from these holiday parks in Kent.

Still searching for your perfect holiday? Then check out the full list of holiday cottages in Kent