Vacation rentals in Maidstone District

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Top-rated vacation rentals in Maidstone District

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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
4.99 out of 5 average rating, 186 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 charming exterior view of the property is featured, with a flowering wisteria vine cascading along the brick wall. The lawn stretches out, bordered by hedges and trees under a blue sky, creating a serene outdoor setting.
Home in Egerton
4.98 out of 5 average rating, 152 reviews

Little Appleby

Dog friendly Little Appleby is located in Egerton, rural Kent, the Garden of England. We are well placed for the tunnel with Folkestone, Le Shuttle 20 miles away. Egerton, adjacent to Pluckley boasts many lovely country walks with the villages of Goudhurst and Sissinghurst within 20 minutes. Rye, Canterbury & Whitstable are within 40 minutes Ashford Designer outlet is 25 minutes away. The nightly rate is £100. The total cost is £117, inclusive of airbnb fees. I do not charge a cleaning fee.

Top guest favourite
A small wooden cabin is set against a backdrop of lush greenery and a clear blue sky. Several sheep graze peacefully in the vibrant green grass surrounding the cabin, with a wooden fence delineating the area.
Farm stay in Biddenden
4.97 out of 5 average rating, 287 reviews

Ayleswade shepherd hut in Kent countyside

set in the small village of biddenden in the heart of the kent countryside belonging to a local farming family of many generations .You can expect beautiful country walks with many footpaths and local villages nearby for cream teas and lovely lunches , the nearby village of Headcorn with its straight connections to London or the coast is good for sightseeing, you wake up to views of our sheep and free range chicken and enjoy a relaxing cup of tea.Theres milk ,tea and coffee and our eggs for you

Top guest favourite
The exterior of a charming two-story cottage features a mix of red brick and light-colored siding. A prominent chimney extends from the roof, while neatly trimmed hedges and colorful flowers line the pathway leading to the entrance, framed by lush greenery in the background.
Cottage in Kent
4.94 out of 5 average rating, 101 reviews

Step back in history and stay in a 14th c home

A 14th Century self contained wing off the main house set in a peaceful location just outside Faversham, Kent. This charming cottage is ideal for anyone wanting to explore Kent. Or if you just want to relax, bring a book or two and relax in front of the woodburner fire. There are bridleways and public footpaths on the doorstep, which are beautiful anytime of the year, being in the heart of the Garden of England. There are many National Trust/ English Heritage attractions in close proximity.

Guest favourite
The exterior of the farmhouse showcases a charming white facade with green trim. Quiet gardens filled with lush greenery and blooming flowers surround the building, providing a serene and inviting atmosphere. Large windows allow natural light to illuminate the interior spaces.
Home in Kent
4.97 out of 5 average rating, 147 reviews

Farmhouse 4 posters cinema music room AGA kitchen

Chilston Home Farm is a period farmhouse in the middle of Kent, the Garden of England. We have lovely walks right from the door, it's perfect for exploring historic Kent and there's easy access to trains to London & Europe. You’ll love the period ambiance: the kitchen Aga, cosy log fires. Two of the bedrooms have king-size four-posters. There's even a bijou cinema! Lots of books & games, a piano, guitar & drums for music lovers, pool table & darts. Ideal for couples or larger families.

Top guest favourite
A cozy seating area features plush, neutral-toned sofas adorned with decorative pillows. A rustic wooden coffee table sits at the center, complementing the warm wooden accents on the walls. Soft lighting creates an inviting ambiance in this thoughtfully designed space.
Farm stay in Oad Street
4.95 out of 5 average rating, 200 reviews

Unique Self contained lodge within stable setting

This unique stylish property is very close to junction 5 on the M2 with easy access to London. Plan your visits to Canterbury Cathedral, Leeds Castle, Whitstable, Rochester Castle and many other tourist attractions with ease from this central location. The Property is two miles from the closest shop and the nearest train station is Sittingbourne. The property is set amongst beautiful paddocks with horses in livery in the adjacent stables. There is ample secure parking and easy access.

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, 289 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 in Boughton Monchelsea
4.9 out of 5 average rating, 790 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.

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 in Wateringbury
4.99 out of 5 average rating, 262 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*

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 in Marden
4.99 out of 5 average rating, 571 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.
Guesthouse in Kent
4.99 out of 5 average rating, 293 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 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
4.9 out of 5 average rating, 216 reviews

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. .

Popular amenities for Maidstone District vacation rentals

Quick stats about vacation rentals in Maidstone District

  • Total rentals

    780 properties

  • Nightly prices starting at

    $28 CAD before taxes and fees

  • Total number of reviews

    30K reviews

  • Family-friendly rentals

    350 properties are a good fit for families

  • Pet-friendly rentals

    260 properties allow pets

  • Rentals with a pool

    40 properties have a pool

Destinations to explore

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