Holiday rentals in Maidstone District

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Top-rated holiday rentals in Maidstone District

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The entrance to The Annex features a well-defined porch with a welcoming door. Flower pots with red blooms sit on either side of the entrance, while a gravel pathway leads up to the front, framed by greenery from nearby plants.
Home
4.99 out of 5 average rating, 190 reviews

Self-contained luxury annex

The Annex is a completely private part of our house for guests exclusive use, located in the historical Kentish village of Leeds, within walking distance to stunning Leeds Castle. Located 5 minutes from J8 M20. Ideal for Leeds Castle. The Kent show ground. 35 mins drive to Eurotunnel & 50 mins to Dover ferry port. 1 hour to London via train. The Annex has it's own private entrance, rear private patio area, sitting room/ fully equipped kitchenette, downstairs shower room/ large upstairs bedroom.

Guest favourite
The exterior of a modern annex is depicted, featuring a sloped roof, large windows, and a wooden deck. Surrounding greenery includes well-maintained grass and flowering plants, contributing to a calming outdoor environment. The scene is set against a backdrop of cloudy skies.
Guest house
4.87 out of 5 average rating, 191 reviews

Adorable 1 bed guesthouse with patio

Sit back & relax in this calm, cosy space. Set within the grounds of our gated family home in Detling located on the slope of the North Downs, 4 miles north east of Maidstone, & on the Pilgrims' Way. Whether you want a relaxing get away or want to explore many of the wonderful walks and bike trails the north downs have to offer you can be sure to find a warm and cosy place to stay at the end of the day. We have a very friendly dog who will be on hand to greet you along with 2 young children

Superhost
A modern kitchen area features sleek dark cabinetry and stainless steel appliances, including an oven and microwave. Two pendant lights hang above a wooden bar with seating for two. A light gray sofa is positioned nearby, complemented by an orange decorative pillow.
Flat
4.88 out of 5 average rating, 131 reviews

The Bohemian Basement

The Bohemian Basement is a unique stylish one bed apartment with its own private garden in the heart of Maidstone. The apartment is 1 of 3 within a newly converted Victorian property just minutes walk from the town centres shops, restaurants and bars. Perfectly equipped with everything you’ll need while visiting Maidstone and with the added bonus of having a wonderful private outdoor garden space, makes this a fantastic Airbnb. There is free on street permit parking which we supply.

Top guest favourite
An exterior view of a barn features a neatly maintained lawn, framed by a stone structure. Double glass doors lead into the barn. Two small chairs are positioned on a paved patio area near the entrance, inviting relaxation. Surrounding greenery adds a natural touch.
Guest house
4.97 out of 5 average rating, 296 reviews

Adorable 1 bedroom guest barn, Boughton Monchelsea

This barn is situated in the picturesque village of Boughton Monchelsea. It has its own private garden with stunning meadow views. It has lots of local amenities to explore and is only 15 minutes drive from Leeds castle and a 15 minute drive to the train station which will take you directly into London. The exposed oak beamed barn is situated next to a traditional oast house, perfect for romantic getaways and people who want to escape the fast pace of everyday life.

Guest favourite
The exterior of the annex is presented, featuring a white picket fence and a gravel area. A vintage lamppost stands near the entrance, complemented by two outdoor chairs positioned on the patio. The structure showcases a pitched roof, rustic siding, and several windows, providing ample natural light.
Cottage
4.9 out of 5 average rating, 794 reviews

The Oast Cottage: Private Annex with own entrance.

We are pleased to offer our refurbished annex with double bedroom, private bathroom, own front door and a private field for dogs. Oast Cottage is a converted stables attached to the main Oast House. The Oast is set in a conservation area of Boughton Monchelsea which consists of converted farm buildings, listed houses and a 16th Century pub (directly opposite). The area boasts many places to visit (including Leeds Castle), countryside walks, as well as numerous pubs.

Guest favourite
The exterior of the lodge showcases a modern structure with dark wood siding, complemented by multiple large windows. Sunlight filters through the trees, illuminating the gravel parking area in front. A inviting entrance can be seen leading into the accommodation.
Cottage
4.97 out of 5 average rating, 211 reviews

Northdown Lodge

We are a unique rural modern lodge with every luxury, nestled in 3 acres. Beautiful views and walking on the Northdown's way. Great local pubs to enjoy. No better place to relax and unwind watching amazing sunsets, and perhaps sampling our local wine grown next door. Or put your feet up by the log burner and watch a film from our vast collection, perhaps with a homemade afternoon tea (available to book in advance). Whatever your preference, you wont be disappointed.

Top guest favourite
An open plan living area features a circular wooden table surrounded by teal chairs and a cozy seating arrangement with a leather sofa and armchair. A television is positioned beside a decorative fireplace, while natural light filters in through windows overlooking lush greenery.
Guest suite
4.99 out of 5 average rating, 266 reviews

Peaceful apt, views, garden, WiFi & sunsets

Relax or work in this stylish apartment with private courtyard garden and vintage summerhouse * First floor apartment with free parking * Country views * Wi-Fi * Self check in * 6ft super king bed * Heating * Smart TV * Plus a summerhouse * Under 1 hour train from London * Local pub/food 10 minute walk * Close to country walks * River Medway 1 mile for boating/walks * Not suitable for pets or children * Please note EV charging is NOT permitted on the property*

Guest favourite
Double doors open to a private garden highlighting a well-maintained lawn and patio area. A circular table with ornate chairs is positioned centrally, and a barbecue station is visible in the background. The scene is illuminated by natural sunlight.
Home in Kent
4.92 out of 5 average rating, 291 reviews

Hermitage Cottage cosy 1-4 person accommodation.

Hermitage Cottage offers annexe accommodation. Bathed in sunshine in private garden setting. We are a commuters dream with Barming railway station at the door. London Victoria 57 minutes and Maidstone East just three minutes by rail. Fully fenced with garaging for one vehicle., entry by automatic gates. Finished to a very high standard with under floor heating and feature fire place. Your every comfort is assured. Welcome pack included.

Top guest favourite
A spacious living area showcases wooden beams and an open layout. A comfortable sofa faces a wood-burning stove, with a flat-screen TV nearby. The dining table is surrounded by woven chairs, and large windows provide natural light while offering views of the entrance and surrounding nature.
Cottage
4.99 out of 5 average rating, 574 reviews

The Lodge

**Opted in to Airbnb's enhanced cleaning protocol** Cosy barn-style accommodation nestled in the heart of the Kent countryside. Located close to National Trust sites and country walks. The Lodge is the perfect country getaway and romantic retreat. Please note this is strictly a NO SMOKING property inside the Lodge, the garden and surrounding field. The property is also NOT SUITABLE for infants, children or pets. Two adults only.

Top guest favourite
A spacious room features a super king bed adorned with crisp white linens, flanked by bedside tables with floral lamps. A comfortable sofa in a muted blue hue is positioned in front, inviting relaxation. Natural light enters through a window, illuminating the warm wooden flooring.
Guest house
4.99 out of 5 average rating, 295 reviews

The Old Engineer, a rural boutique retreat

Our rural boutique accommodation with private entrance and pretty courtyard garden is surrounded by fields. The space is designed with the guests comfort and luxury in mind. It is the perfect spot for a relaxing and peaceful get away. Super king bed (or twin if requested). Located between Tunbridge Wells and Maidstone, close to the Hop Farm and attractions such as Sissinghurst Gardens, Vineyards and many NT properties.

Guest favourite
The open-plan lounge features a vaulted ceiling and is furnished with a spacious light grey sofa, complemented by decorative cushions. A flat-screen TV is positioned on a white media console, with a log burner highlighted beside it. Natural light enters through the window, adorned with simple blinds.
Cabin
4.86 out of 5 average rating, 366 reviews

The Heath large log cabin Maidstone

Large detached one bedroom log cabin with open plan kitchen/lounge which has a vaulted ceiling. Has its own side entrance and is totally separate from the main house. We also have off street parking for 1 car. Ideal if you want to get away from it all for a few days or weeks. Located 2 minutes from J7 M20 close to Maidstone. Ideal for Leeds Castle. The Kent show ground. and Kent life. The Maidstone studios.

Guest favourite
A pathway bordered by lush greenery leads to a wooden gate. A small birdhouse stands nearby, surrounded by scattered stones. The area is illuminated by natural light, showcasing a serene garden setting with a hint of rustic charm.
Guest suite
4.72 out of 5 average rating, 210 reviews

Charming Valence Green Cottage Annexe

Spacious double bedroom in annexe with kitchenette and shower room. Free parking, Sky TV and WiFi as well as own entrance and outdoor space. Ideal for short stays. Please take care on the path down to the annexe as when it has been raining it can be a bit slippery. If you are going to arrive after dark and would like the outside lights left on please don't hesitate to let me know

Popular amenities for Maidstone District holiday rentals

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Quick stats about holiday rentals in Maidstone District

  • Total holiday rentals

    Explore 780 holiday rentals in Maidstone District

  • Nightly prices starting at

    Maidstone District holiday rentals start at £15 per night before taxes and fees

  • Verified guest reviews

    Over 29,960 verified reviews to help you choose

  • Family-friendly holiday rentals

    350 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 260 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    360 properties have a dedicated workspace

  • Wifi availability

    710 of Maidstone District holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Maidstone District rentals

  • 4.8 Average rating

    Maidstone District stays are highly rated by guests – averaging 4.8 out of 5!

Destinations to explore

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  5. Maidstone District