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Holiday Cottages In Maidstone To Rent

Home to the 'loveliest castle in the world', Maidstone is the historic jewel in Kent's gleaming crown, and a wonderful southeastern break. We’ve got plenty of holidays cottages in Maidstone that'll bring you close to not only the famous grandeur of Leeds castle, but Maidstone’s wonderful river passageways, country parks, museums and more. And if after a break away from the hustle and bustle, you can always immerse yourself in a world of hideaway Tudor houses and intimate gastro pubs, as Maidstone has it all.

Maidstone lives up to Kent’s ‘Garden of England’ nickname, with a scattering of beautifully manicured gardens, wild river valleys and age-old woodland. In love with England of the past, whilst still embracing the modern life of bustling high streets and high-adrenaline adventure parks, Maidstone is a diverse destination full of rustic and contemporary holiday cottages. If you want that bit-of-everything break, then Maidstone might just be the perfect spot!

Maidstone Cottages

  • Special Offers Available

    • Last Minute Cottages - Tasteful Maidstone Rental S10457

    Tasteful MAIDSTONE Rental

    South East Kent Maidstone

    S10457

    This property can be booked in conjunction with MD439 D'Arcy Spice  to sleep up to 10


    One of two attractive semi-detached cottages at the heart of a working soft fruit farm - S10457 is named after...

  • Special Offers Available

    • Last Minute Cottages - Tasteful Maidstone Apartment S44913

    Tasteful Maidstone Apartment

    South East Kent Maidstone

    S44913

    A great country retreat. This romantic hideaway makes the perfect base for two in a peaceful and tranquil setting.

    S44913 is a quaint and comfortable property adjacent to the owner’s home. Located in a rural area near Maidstone, ...

  • Special Offers Available

    • Last Minute Cottages - Adorable Maidstone Cottage S24489

    Adorable Maidstone Cottage

    South East Kent Maidstone

    S24489

    Enjoy a holiday in this unique property, formerly a water tower, with plenty of activities nearby, including walking and pony trekking.
    Sympathetically converted to provide quality holiday accommodation with unique circular rooms, this spaci...

  • Special Offers Available

    • Last Minute Cottages - Luxury Maidstone Cottage S41311

    Luxury Maidstone Cottage

    South East Kent Maidstone

    S41311

    You may want to visit Eagle heights, one of the UK’s largest bird centres, or experience a track day driving experience.
    This thoughtfully furnished boutique-style holiday cottage makes an ideal base in rural Kent, ‘The Garden of...

  • Special Offers Available

    • Last Minute Cottages - Delightful Maidstone Apartment S24502

    Delightful Maidstone Apartment

    South East Kent Maidstone

    S24502

    Enjoy unlimited free access to Leeds Castle during your stay within the grounds and children will love the playground and falconry display.
    Indulge yourself in a unique holiday cottage experience within the 500-acre parkland estate at Leeds ...

  • Special Offers Available

    • Last Minute Cottages - Inviting Maidstone Rental S10325

    Inviting MAIDSTONE Rental

    South East Kent Maidstone

    S10325

    This property can be booked in conjunction with MD440 Innishfree to sleep up to 10


    Set in the heart of a working fruit farm are two beautifully converted semi-detached cottages. The farm originally pro...

  • Special Offers Available

    • Last Minute Cottages - Captivating Maidstone Rental S10532

    Captivating MAIDSTONE Rental

    South East Kent Maidstone

    S10532

    S10532 is a wonderful, single storey farm building conversion, covering 84 square metres ,sitting across the drive from the owners stunning Listed farmhouse which is set in two acres of glorious gardens in an Area ...

  • Special Offers Available

    • Last Minute Cottages - Exquisite Maidstone Lodge S105751

    Exquisite Maidstone Lodge

    South East Kent Maidstone

    S105751

    Keeper Cabin is a single-storey log cabin nestled on the owner’s working farm set in the picturesque Kent countryside.
    These two detached, single-storey log cabins are nestled on the owner’s working sheep and pheasant farm in the...

  • Special Offers Available

    • Last Minute Cottages - Charming Maidstone Apartment S24499

    Charming Maidstone Apartment

    South East Kent Maidstone

    S24499

    Beautifully located within the grounds of Leeds Castle which is at your disposal during your stay in this unique location.
    Indulge yourself in a unique holiday cottage experience within the 500-acre parkland estate at Leeds Castle, referred ...

  • Special Offers Available

    • Last Minute Cottages - Wonderful Maidstone Cottage S24494

    Wonderful Maidstone Cottage

    South East Kent Maidstone

    S24494

    With wheelchair access and all on the ground floor this barn makes a great base for touring The Garden of England.
    Converted to a good standard, the adjoining Bearsted Barns reside in an Area of Outstanding Natural Beauty in the owner’...

  • Special Offers Available

    • Last Minute Cottages - Gorgeous Maidstone Rental S25419

    Gorgeous Maidstone Rental

    South East Kent Maidstone

    S25419

    S25419 is a barn conversion in the village of East Farleigh just three miles from Maidstone. The cottage sleeps six people in one king-size double bedroom with en-suite shower, one twin with single (on request), one single bedroom and one cot room...

  • Special Offers Available

    • Last Minute Cottages - Captivating West Farleigh Rental S10439

    Captivating WEST FARLEIGH Rental

    South East Kent Maidstone West Farleigh

    S10439

    Set in stunning farmland with far reaching views over the surrounding countryside, a row of hop pickers' cottages have been charmingly converted to provide attractive and comfortable accommodation, which is all on one level. The character ...

  • Special Offers Available

    • Last Minute Cottages - Gorgeous Maidstone Cottage S40968

    Gorgeous Maidstone Cottage

    South East Kent Maidstone

    S40968

    With its private garden, Lily’s Barn is ideally located for a countryside break and close to walking routes and an RSPB site.
    This renovated barn, which is attached to the owner’s property, is at the end of a quiet lane, surround...

  • Special Offers Available

    • Last Minute Cottages - Charming Maidstone Cottage S24492

    Charming Maidstone Cottage

    South East Kent Maidstone

    S24492

    Part of a Kentish oast house and adjoining the owner’s home, this cosy holiday cottage, in an AONB, is in a tiny hamlet by the historic church of St Catherine Kingsdown. With direct access to public footpaths over fields and woodland. Doddingto...

  • Special Offers Available

    • Last Minute Cottages - Stunning Maidstone Cottage S24509

    Stunning Maidstone Cottage

    South East Kent Maidstone

    S24509


    S24509 has been converted from a 1930s bungalow to a contemporary dormer bungalow with conservatory. This detached holiday property, adjacent to the owners’ home, is located on the picturesque Isle of Sheppey. With views of the sea and a ...

  • Special Offers Available

    • Last Minute Cottages - Attractive Maidstone Apartment S24505

    Attractive Maidstone Apartment

    South East Kent Maidstone

    S24505

    Indulge yourself in a unique holiday cottage experience within the 500-acre parkland estate at Leeds Castle, referred to as ’The loveliest castle in the world’. It is set on two islands on the River Len in the heart of the county of Kent, renow...

  • Special Offers Available

    • Last Minute Cottages - Adorable Maidstone Cottage S44380

    Adorable Maidstone Cottage

    South East Kent Maidstone

    S44380

    S44380 is a quaint and comfortable, semi-detached annexe, attached to the owners’ home and located in the countryside of Trottiscliffe in Kent. Accessed by a rough track and boasting stunning views across the rolling hills, guests can enjoy a r...

  • Special Offers Available

    • Last Minute Cottages - Captivating Maidstone Cottage S24488

    Captivating Maidstone Cottage

    South East Kent Maidstone

    S24488

    Originally stables to the main farmhouse, this 16th-century Grade II listed property has been carefully converted to provide an ideal holiday base from which to explore the ‘Garden of England’. Set in the heart of the North Downs, surr...

  • Special Offers Available

    • Last Minute Cottages - Inviting Maidstone House S42558

    Inviting Maidstone House

    South East Kent Maidstone

    S42558

  • Special Offers Available

    • Last Minute Cottages - Splendid Marden House S72450

    Splendid Marden House

    South East Kent Maidstone Marden

    S72450

    Sleeps 15

  • Special Offers Available

    • Last Minute Cottages - Wonderful Headcorn Rental S10394

    Wonderful HEADCORN Rental

    South East Kent Maidstone Headcorn

    S10394

    This wonderful country house is an interior designers dream - fantastic decor, furniture and real wow! factor. Add to this the "dancing horses" in the dressage yard right behind the house - making this a very special holiday base.


    • ...

  • Special Offers Available

    • Last Minute Cottages - Superb Staplehurst Rental S10444

    Superb Staplehurst Rental

    South East Kent Maidstone Staplehurst

    S10444

    An immaculate, detached holiday cottage, built and maintained to a high standard and located in peace and tranquillity in the grounds of the owners' modern family house, yet with privacy and the use of a rear fenced garden, large front gar...

  • Special Offers Available

    • Last Minute Cottages - Superb Staplehurst Rental S10455

    Superb Staplehurst Rental

    South East Kent Maidstone Staplehurst

    S10455

    S10455 is a detached barn conversion located off a quiet country lane in the grounds of the owners' 16th century farmhouse. It has a spectacular living area with an entertainment centre, luxury bathrooms and bedrooms all with exposed beams...

  • Special Offers Available

    • Last Minute Cottages - Luxury Maidstone Rental S10344

    Luxury MAIDSTONE Rental

    South East Kent Maidstone

    S10344

    This beautifully renovated former farm workers cottage sits high above The Weald and has the most breathtaking views over the rolling Kent countryside. It is a "mirror image" of Weald View (MD442) which is attached and has been decorated a...

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