Vacation rentals in Maidstone District

5 out of 5 average rating, 153 reviews

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 in Leeds

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.

4.87 out of 5 average rating, 176 reviews

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.

Guesthouse in Detling

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

4.92 out of 5 average rating, 135 reviews

An aerial view showcases multiple transparent bubbles nestled within a green landscape. Each bubble features unique geometric rugs and comfortable seating options. Surrounding gravel paths and patches of grass enhance the natural setting, complemented by trees that provide a serene backdrop.

Farm stay in Kent

Grand Bubble

Grand bubble sleeps 4 people who can enjoy the ultimate view of nature. You can fall asleep with the stars and wake up to the rising sun. This bubble has the wow factor and includes your own hot tub, BBQ, a shower, a flushing toilet, outdoor chess set and a golf buggy. The bubble is very secluded set at a bottom of a 12 acre field off a woodland. Out side of the bubble is a very large outdoor gazebo with comfy seating and a large gas bbq so even if it rains you can still bbq comfortably.

4.88 out of 5 average rating, 128 reviews

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.

Apartment in Kent

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.

Cottage in Boughton Monchelsea

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.

4.9 out of 5 average rating, 743 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.

4.97 out of 5 average rating, 205 reviews

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 in Kent

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.

Guest suite in Wateringbury

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.

4.99 out of 5 average rating, 249 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*

4.92 out of 5 average rating, 275 reviews

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

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.

4.99 out of 5 average rating, 283 reviews

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.

Guesthouse in Kent

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.

4.9 out of 5 average rating, 210 reviews

The exterior of the studio is highlighted by a wooden deck area with turquoise chairs, accessed by a staircase. Lush greenery and flowering plants surround the entrance, while a gravel pathway leads to the studio. The historic Oast house is visible in the background.

Farm stay in Kent

Home Farm Oast Studio

The Studio is in rural location in the garden of a historic Kentish Oast House with views across paddocks and woodland. It is situated above a barn style garage and is self contained with complete privacy. It has a Large bedroom, ensuite bathroom with shower, a modern fitted kitchen and has an outside wooden deck area with bistro table and chairs for your relaxation. Ideal for couples and business travellers. .

4.86 out of 5 average rating, 357 reviews

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 in Penenden Heath

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 suite in Sutton Valence

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.

4.7 out of 5 average rating, 197 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

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Maidstone District vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Maidstone District

5 out of 5 average rating, 65 reviews

The interior features wood-paneled walls, creating a warm ambiance. A vintage world map is displayed prominently above two neatly made beds, each adorned with tropical-patterned bedding and contrasting yellow pillows.

Bus in Hollingbourne

Minty the green bus conversion

4.85 out of 5 average rating, 65 reviews

A spacious living area is highlighted by a tall ceiling and large window allowing natural light to fill the space. A leather sectional sofa is accompanied by decorative pillows, while a wooden coffee table sits on a soft rug. A small TV is positioned on a light-colored cabinet.

Guest suite in Kent

A Cosy Hideaway in Kent

4.96 out of 5 average rating, 69 reviews

The modern countryside house features a striking angular design with large glass panels reflecting the sky. A spacious lawn surrounds the property, complemented by a patio and outdoor seating area. Lush greenery provides a natural border, enhancing the tranquil outdoor setting.

Barn in Sutton Valence

The Barnyard

5 out of 5 average rating, 4 reviews

The guest bedroom features two beds, one with a cushioned base and the other with wooden framing. Soft lighting is provided by bedside lamps beside each bed. Fresh towels are neatly placed on the beds, enhancing the clean and organized appearance of the room.

Guesthouse in Kent

Newlyn Barn

4.95 out of 5 average rating, 38 reviews

A tranquil orchard path is flanked by flowering cherry trees, with a cozy hut visible in the background. The scene is set against a clear blue sky, and the lush greenery of the grass adds to the serene atmosphere of the secluded location.

Shepherd’s hut in Kent

Cherry Blossom

4.97 out of 5 average rating, 69 reviews

The exterior of a rustic barn highlights natural wood siding under a bright blue sky, accented by wispy clouds. A spacious lawn in front leads to a gravel driveway, with a view of the rolling countryside and distant hills visible in the background.

Guesthouse in Kent

Silverwood Studio Countryside Getaway

5 out of 5 average rating, 7 reviews

A well-lit sleeping area features two spacious beds, each adorned with textured blankets and decorative pillows. Framed floral art pieces hang on the wall above, complemented by soft lighting. Fresh towels are neatly arranged on each bed, contributing to a tidy and inviting environment.

Apartment in Kent

Maidstone Studio