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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

    • Big 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

    • Big 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

    • Big 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

    • Big 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

    • Big 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

    • Big 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

    • Big Cottages - Luxury Maidstone Apartment S24500

    Luxury Maidstone Apartment

    South East Kent Maidstone

    S24500

    With Leeds Castle literally on your doorstep and a free ticket included for guests you will want to return again and again!. Indulge yourself in a unique holiday cottage experience within the 500-acre parkland estate at Leeds Castle, referred to a...

  • Special Offers Available

    • Big Cottages - Adorable Maidstone Cottage S24506

    Adorable Maidstone Cottage

    South East Kent Maidstone

    S24506

    A quiet rural retreat
    Winners of a 2015 Visit England ROSE award for service excellence, the owners of S24506 have been recognised for truly going the extra mile for their guests.

    S24506 at Tudor Barn is a detached, converted propert...

  • Special Offers Available

    • Big Cottages - Splendid Marden House S72450

    Splendid Marden House

    South East Kent Maidstone Marden

    S72450

    Sleeps 15

  • Special Offers Available

    • Big Cottages - Beautiful Maidstone Cottage S24496

    Beautiful Maidstone Cottage

    South East Kent Maidstone

    S24496

    Within easy reach of a mainline train station with links to London or enjoy the tranquillity of the countryside in this conservation area.
    This stylishly renovated, semi-detached holiday barn lies on the edge of a very pretty village on the ...

  • Special Offers Available

    • Big Cottages - Luxury Maidstone House S3554

    Luxury Maidstone House

    South East Kent Maidstone

    S3554

    Shepherd's Farm House is a detached farmhouse on the edge of the Kent village of Lenham Heath near to Ashford. The cottage has two double bedrooms, one twin room, one single room with an ensuite and a family bathroom, making it suitable for seven ...

  • Special Offers Available

    • Big 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

    • Big 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

    • Big Cottages - Splendid Staplehurst Rental S10353

    Splendid Staplehurst Rental

    South East Kent Maidstone Staplehurst

    S10353

    This gorgeous oast house, set within ten acres of grounds which includes paddocks, fields and orchards, has been converted with great style by the owners to provide wonderful accommodation for all the family - including...

  • Special Offers Available

    • Big Cottages - Exquisite Maidstone Apartment S24501

    Exquisite Maidstone Apartment

    South East Kent Maidstone

    S24501

    Indulge in a unique holiday experience within the grounds of Leeds Castle, and enjoy free access to the castle and grounds for the whole party.
    Indulge yourself in a unique holiday cottage experience within the 500-acre parkland estate at Le...

    Sleeps 10

  • Special Offers Available

    • Big Cottages - Tasteful Maidstone Cottage S60824

    Tasteful Maidstone Cottage

    South East Kent Maidstone

    S60824

    S60824 is a spacious semi-detached Edwardian villa, set over four floors, on the edge of bustling Maidstone. It sleeps eight people in four bedrooms, a king-size double with an en-suite bathroom, a double with an en-suite shower room, a further do...

  • Special Offers Available

    • Big Cottages - Exquisite Maidstone Rental S13260

    Exquisite MAIDSTONE Rental

    South East Kent Maidstone

    S13260

    These two beautifully renovated semi-detached former farm workers cottages sit high above The Weald and are perfect for friends or familty wanting to reunit and holiday together. Each property offers your own personal s...

  • Special Offers Available

    • Big Cottages - Inviting Maidstone Cottage S79080

    Inviting Maidstone Cottage

    South East Kent Maidstone

    S79080

    S79080 is a stunning converted Victorian farm building offering exceptional accommodation with many luxurious touches to make your holiday really special. It is situated in its own pretty courtyard garden, within the grounds of the owners 17th ...

  • Special Offers Available

    • Big Cottages - Superb Hunton Rental S10520

    Superb Hunton Rental

    South East Kent Maidstone Hunton

    S10520

    This self-contained annexe to a large house set in a beautiful country garden makes an excellent base for a relaxing break or for visiting the many attractions in Kent, Sussex and beyond. The Granary is a charming, spacious home in a rural...

  • Special Offers Available

    • Big Cottages - Wonderful Marden Cottage S39583

    Wonderful Marden Cottage

    South East Kent Maidstone Marden

    S39583

    Lovely converted coach house on outskirts of village in a quiet rural location within the grounds of the owners house.

    Size: Sleeps up to 5, 2 bedrooms
    Nearest beach: 24 miles
    Nearest amenities: 1 miles
    ...

  • Special Offers Available

    • Big Cottages - Gorgeous Lenham Rental S10400

    Gorgeous Lenham Rental

    South East Kent Maidstone Lenham

    S10400

    This three storey former shop has origins dating back to the 1700s, has a pretty interior with ancient beams and provides a comfortable, well-equipped base for touring the Heart of Kent. The village of Lenham offers a good selection o...

  • Special Offers Available

    • Big Cottages - Tasteful Sutton Valence Lodge S83932

    Tasteful Sutton Valence Lodge

    South East Kent Maidstone Sutton Valence

    S83932

    S83932 sits in an elevated position with wonderful far reaching views across the Weald of Kent. Originally a fruit pickers bothy it has...

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