Holiday houses 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
Condo in Wateringbury
4.99 out of 5 average rating, 286 reviews

Stylish Apartment With Private Summerhouse &Garden

Escape to the Kent countryside in this stylish, totally private apartment with your own courtyard garden plus a charming vintage summerhouse - perfect for relaxing weekend breaks just 1 hour from London. Ideal for couples looking for a peaceful countryside escape, offering rural views, countryside walks nearby and a local pub within a 12 min stroll. With self check in, parking and your own private entrance, it’s an easy base to unwind and explore Kent’s villages, vineyards and historic houses.

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 in Leeds
5 out of 5 average rating, 250 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
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
4.91 out of 5 average rating, 151 reviews

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.

Top Guest favourite
An inviting hot tub is nestled under a canopy, adorned with twinkling fairy lights and decorative flowers. Surrounding the hot tub, gravel is laid out, and comfortable seating is positioned nearby, enhancing the serene ambiance of the private garden space.
Place to stay in Lynsted
5 out of 5 average rating, 520 reviews

Romantic Hideaway & Hot tub in Kent Countryside.

A White Romantic Garden Cottage & Luxury Hot Tub set in the heart of the Kent Countryside with idyllic views across our orchards . Disconnect with the world, relaxing in the Hot Tub, tucked away in the Private woodland setting surrounded by twinkling fairy lights under the starry sky. The Cottage has been designed to provide comfort, space & tranquillity with its vaulted ceilings & private gardens & summerhouse & parking. Pubs are within walking distance & a nearby Forest to explore .

Superhost
A coffee tray is elegantly arranged with a French press and two clear glasses. The background features a wooden kitchen island illuminated by warm pendant lights, with a soft-focus on the living area that suggests a relaxed environment.
Apartment in Kent
4.88 out of 5 average rating, 133 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.

Guest favourite
A charming cottage exterior is framed by lush greenery and mature trees. The building features a traditional wooden door and a large window, allowing natural light to fill the interior. Gravel pathways lead to the entrance, enhancing the rustic appeal of the setting.
Cottage in Delting
4.86 out of 5 average rating, 203 reviews

Cottage in the Wood, Detling

'Cottage in the Wood' contains two double bedrooms one with en-suite bath/shower and one with shower room along with a sheltered hot tub taking advantage of the rolling Kent countryside with extensive views over the local Vineyards and North Downs beyond. The small and picturesque village of Detling is found on the slope of the North Downs, just northeast of Maidstone, and on the Pilgrims' Way - ideal if you're looking for a break only a short distance away from London.​

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.
Guesthouse in Boughton Monchelsea
4.97 out of 5 average rating, 351 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
Cottage in Boughton Monchelsea
4.9 out of 5 average rating, 895 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
Cottage in Kent
4.96 out of 5 average rating, 226 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.

Guest favourite
A spacious living area features a large, light-colored sectional sofa adorned with various cushions. A minimalist coffee table is positioned in front, with soft lighting highlighting the wood panel walls and ceiling. The kitchen area, defined by sleek cabinetry, is partially visible in the background.
Barn in Kent
4.96 out of 5 average rating, 129 reviews

Acorn Lodge @ The Oaks Retreat

This memorable place is anything but ordinary. It is The Oaks Retreat, WINNER of the Paris Design awards 2024 'best hospitality interior', an architecturally inspired bespoke woodland Airbnb located in the seaside town of Whitstable. The Acorn Lodge is a bespoke 1 king size bedroom retreat fully customized with high-end finishes. It must be seen in person to be fully appreciated. Our Wellness area is equipped with a log sauna, a cold plunge and outdoor shower.

Top Guest favourite
Bungalow in Kent
4.97 out of 5 average rating, 103 reviews

Luxury Spa Retreat: Sauna & Hot Tub

Escape to our exclusive gated spa retreat, nestled on 5.5 acres of serene countryside in picturesque Fawkham, Kent. This private and tranquil haven offers breathtaking views of rolling hills, perfect for relaxation. Unwind in the luxurious sauna, steam room, or hot tub, soaking in the peace after exploring local attractions. Just minutes from Brands Hatch, our retreat blends seclusion with convenience, your ultimate quiet getaway awaits.

Top Guest favourite
The exterior of a rural boutique accommodation is shown. A gravel pathway leads to the entrance, framed by carefully maintained gardens featuring flowering trees and greenery. The structure, clad in dark wood, has large windows that invite natural light, enhancing the serene rural setting.
Guesthouse in Kent
4.99 out of 5 average rating, 302 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.

Popular amenities for Maidstone District holiday rentals

When is the best time to visit Maidstone District?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Maidstone District?

    Maidstone District has more than 340 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cabin rentals in Maidstone District?

    Experience the best of Maidstone District with our cabin rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Maidstone District?

    Four-legged friends are welcome in Maidstone District. Choose from more than 270 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Maidstone District?

    Yes! Work meets play with ease at over 360 vacation rentals in Maidstone District featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Maidstone District vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Maidstone District, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Maidstone District?

    Make yourself at home in Maidstone District by choosing from our most frequently booked neighborhoods. We have over 120 vacation rentals in East Farleigh, over 460 vacation rentals in Bearsted, and over 50 vacation rentals in Snodland.

  • Do house rentals in Maidstone District have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Maidstone District. Enjoy a tailored experience with all the comforts you desire.

  • Do shepherds hut rentals in Maidstone District have a kitchen?

    Absolutely! We offer over 10 shepherds hut rentals with a kitchen in Maidstone District. Enjoy a tailored experience with all the comforts you desire.

  • Do barn rentals in Maidstone District have wifi?

    Absolutely! We offer over 40 barn rentals with wifi in Maidstone District. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Maidstone District have free parking?

    Absolutely! We offer over 70 apartment rentals with free parking in Maidstone District. Enjoy a tailored experience with all the comforts you desire.

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 $28 AUD per night before taxes and fees

  • Verified guest reviews

    Over 31,530 verified reviews to help you choose

  • Family-friendly holiday rentals

    340 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 270 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    360 properties have a dedicated workspace

  • Wi-Fi availability

    710 of Maidstone District holiday rentals include Wi-Fi 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

  1. Airbnb
  2. United Kingdom
  3. England
  4. Kent
  5. Maidstone District