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 in Leeds
5 out of 5 average rating, 227 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.

Top guest favourite
A wooden deck with steps leads to the entrance of the barn. The exterior showcases a gray wooden facade, framed by greenery, providing a sense of privacy. Windows are visible, allowing natural light to enter the space.
Guest house in Kingswood
4.97 out of 5 average rating, 106 reviews

The Strawberry Barns near North Downs Way Kent.

Strawberry Barns are your home-away-from-home in the Kent countryside. Surrounded by the quiet of peaceful woodland, in Bramley Acres in Kingswood, near Maidstone. Strawberry Barns are the ideal base for couples to explore the Kent Downs Area of Outstanding Natural Beauty (AONB), North Downs Way, delightful villages, pleasant woodland trails, and lovely pub walks in the countryside, all within a short distance of 500 acres of beautiful parkland and formal gardens at the historic Leeds Castle.

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.
Flat in Kent
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.

Guest favourite
A light-filled lounge area features natural wood paneling and modern furnishings, including a cozy sofa and round chair. A sliding glass door opens to a grassy outdoor space, while an area rug adds warmth to the contemporary design.
Cabin in Maidstone
4.95 out of 5 average rating, 587 reviews

Cosy Woodland Lodge with alfresco Hot Tub

Embrace the quirky, cosy interiors in this romantic getaway. Open the doors to the terrace, and let the sounds of nature waft through the lodge. Fire up the BBQ, enjoy a good meal and then spend the evening in the hot tub. Perfect for anyone looking to get away from it all The Lodge offers a romantic hideaway, with exclusive use of the hot tub jacuzzi and a low height mezzanine sleeping area on a futon mattress where you can star watch in bed while listening to the local owls.

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 in Boughton Monchelsea
4.97 out of 5 average rating, 327 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, 850 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
A well-lit bedroom features a spacious bed with a combination of white and orange bedding. Two framed artworks are mounted on the wall above the headboard. Natural light streams in from a large window, which offers a view of the surrounding area.
Bungalow in Allington
4.97 out of 5 average rating, 123 reviews

Maidstone Bungalow sleeps 5 with parking

This stylish bungalow boasts with unique features and has everything you need for a comfortable stay. Open plan living space is airy and bright and compliments fully equipped modern kitchen. This 2 bed fully refurbished single level home sleeps up to 5 people and it can provide both king size and single beds. The bungalow is located in a prominent position in Allington, Maidstone, and it offers off road parking for multiple cars and a private garden.

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, 302 reviews

Hermitage Cottage 2 Guests 2 Children.

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
Cottage in Marden
4.99 out of 5 average rating, 594 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
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.
Guest house in Kent
4.99 out of 5 average rating, 298 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
Cabin in Penenden Heath
4.86 out of 5 average rating, 373 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.

Top guest favourite
Guest house in Kent
4.98 out of 5 average rating, 110 reviews

Silverwood Studio Countryside Getaway

Escape to the countryside at Silverwood Studio, based on a farm in the most stunning location in Kent. We have recently renovated this barn to a high standard, complete with a log burner, kitchenette and a large picture window looking over the most fantastic view. It is located in a truly beautiful setting, in the middle of the English countryside, perfect for a romantic getaway or peaceful retreat.

Popular amenities for Maidstone District holiday rentals

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Frequently Asked Questions

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

    Maidstone District has more than 350 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Maidstone District with our barn 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 260 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 370 vacation rentals in Maidstone District featuring dedicated workspaces. Stay connected and productive in your home away from home.

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

    Yes! Dive into the perfect getaway at one of over 20 house rentals 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 470 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 cabin rentals in Maidstone District have a kitchen?

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

  • Do farmstay rentals in Maidstone District have wifi?

    Absolutely! We offer over 20 farmstay rentals with wifi in Maidstone District. Enjoy a tailored experience with all the comforts you desire.

  • Do private suite rentals in Maidstone District have free parking?

    Absolutely! We offer over 10 private suite 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 810 holiday rentals in Maidstone District

  • Nightly prices starting at

    Maidstone District holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 30,980 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

    370 properties have a dedicated workspace

  • Wifi availability

    740 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

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