Guesthouse holiday rentals in Maidstone District

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Top-rated Guesthouses in Maidstone District

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite
A charming exterior view of the converted agricultural building is framed by lush greenery and colorful flowers. The black wooden weatherboarding blends seamlessly with the natural surroundings, while large windows allow glimpses of the interior. The scene is set under a vibrant garden ambiance.
Guesthouse in Marden
4.93 out of 5 average rating, 195 reviews

The Apple Store

The Apple Store is a beautiful and meticulously clean converted agricultural building that sits in the lovely gardens of a 16th Century house. Perfect for a staycation and set in a peaceful, rural location, the property is approximately 1.5 miles from Marden village and .75 mile from Hush Heath vineyard. Ideal for visits to local National Trust and RHS properties like Sissinghurst Castle, Leeds Castle and Great Dixter. Trains from Marden station to London run all day and take less than an hour.

Top Guest favourite
The exterior of the annex is showcased, featuring vertical wooden slats and a glass-paneled door. A small window is visible, allowing natural light into the space. The entrance is set on a paved path, surrounded by greenery and a water storage tank nearby.
Guesthouse in Sittingbourne
4.94 out of 5 average rating, 263 reviews

Self-contained annex, with off-road parking.

Self-contained annex in Sittingbourne, perfect if you are visiting the area for work or leisure. Everything you need for a comfortable stay in your own completely private place, with driveway parking and fast WiFi. The accommodation comprises a bedroom /lounge /working room, kitchen and bathroom. The annex, especially the bedroom, is very quiet and peaceful. Located conveniently for the motorway and also easy access to the town centre, train station, shops, takeaways, restaurants and pubs.

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.
Guesthouse in Detling
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

Top Guest favourite
The exterior of the Strawberry Barn features a green wooden facade, surrounded by lush foliage. A small patio with a bistro table and two chairs provides a space to enjoy the outdoor view. The entrance door is framed by blooming red and green plants.
Guesthouse in Kingswood
4.97 out of 5 average rating, 100 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.

Guest favourite
Guesthouse in Kent
4.92 out of 5 average rating, 116 reviews

'The Hideaway ' Sole Street, Cobham, Kent.

The Hideaway is situated in the heart of Kent in the rural village of Sole Street, Parish of Cobham & Luddesdown. We are walking distance to Sole Street Station on the Victoria line to London. Ebbsfleet & Meopham are a driving distance away so St Pancras and Victoria can be reached in 17 - 35 minutes. The location is great for people who love long walks & nature as we are surrounded by ancient unspoilt woodlands and rolling hills. We have a choice of three Forestry Commission Parks to visit.

Top Guest favourite
The exterior of a self-contained building features a stone facade and a sloped roof. Large windows allow natural light to flood the interior. A wooden bench is positioned in front, alongside a gravel pathway leading to a rustic shed.
Guesthouse in Bethersden
4.96 out of 5 average rating, 127 reviews

The Annexe at Rockley

A contemporary space amongst pretty gardens in rural kent, The Annexe at Rockley is a self contained building. Tucked away down a country lane outside the village of Bethersden it’s an ideal base for walking and cycling or exploring the beautiful surroundings. There is plenty to do in the area for a short break such as visiting the local towns of Tenterden Canterbury and Tunbridge Wells . It’s also well placed for a stopover for anyone heading to France with Eurotunnel only 25 minutes away.

Top Guest favourite
The barn features a charming exterior with wooden siding and a gabled roof. Sunlight filters through lush trees, casting gentle shadows. A fenced garden area surrounds the property, complemented by a gravel pathway leading up to the entrance.
Guesthouse in Smarden
4.97 out of 5 average rating, 158 reviews

Snap Mill Barn Country Holiday Let

Snap Mill Barn is a recently refurbished one bedroom barn located between Pluckley and Smarden in rural Kent. Surrounded by arable farm land with tranquil surrounding country side with a variety of walks at your doorstep. Open plan living with self contained kitchen, lounge dinner complete with log burner and super fast wifi. Stylish bathroom with enclosed shower and all linen and toiletries provided. Fully enclosed patio area. Many local amenities nearby i.e National Trust properties.

Top Guest favourite
A charming outdoor seating area features white metal chairs and a small table set on wooden decking. Potted plants flank the seating arrangement, and a brick wall provides a backdrop. The space is bordered by lush greenery, offering a serene environment.
Guesthouse in Tonbridge
4.97 out of 5 average rating, 315 reviews

Weald Lodge: self-contained annexe with parking

This stylish place to stay is perfect for couples looking for a country get away with walks across the fields. Driving distance to local amenities, pubs/restaurants & attractions. Weald Lodge is a separate annexe in the gardens of Wealdview Farmhouse (TN12 6SP) PLEASE NOTE, despite being in the category of farm, we are not a farm and do not have far machinery. The fields around us have grazing sheep Due to the open beams on the mezzanine level, we don't encourage infants or children

Top Guest favourite
An open-plan living area showcases warm wooden beams and a spacious layout. A comfortable light-colored sofa and ottoman are placed adjacent to a dining table, while a well-equipped kitchen is visible in the background. Fresh flowers accent the dining table, adding subtle elegance.
Guesthouse in Kings Hill
4.96 out of 5 average rating, 279 reviews

Peaceful, charming oak framed annexe

Recently furbished, oak framed annexe building consisting of large open plan lounge, dining and kitchen area. Shower room with hand basin and WC. Upstairs, snug double bedroom. (May be converted to two singles) Extra sofa bed available downstairs so property can accommodate up to 4 guests. Reliable wifi and space for remote working. Small, discreet private patio area. Private parking. Close to golf course and village centre. Surround yourself with style in this standout space.

Guest favourite
Guesthouse in Kent
4.92 out of 5 average rating, 144 reviews

The Whitstable Oyster - a self-contained studio

The Whitstable Oyster is a private, self-contained studio in a converted side building of our family home. Situated on a quiet road, it’s a 10-minute walk to Whitstable’s high street and around 20 minutes to the beach, with a Co-op close by. Inside, you’ll find a king-size bed, TV, compact kitchen with hob and combi-oven, dining table, sofa, and a separate shower room with toilet. Free street parking is available. A practical and comfortable base to enjoy Whitstable from.

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, 299 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.

Top Guest favourite
A charming black timber cottage is surrounded by lush greenery and neatly trimmed hedges. A well-maintained lawn extends in the foreground, leading to a wooden fence that provides a sense of privacy while natural light enhances the serene landscape.
Guesthouse in Biddenden
4.96 out of 5 average rating, 131 reviews

Little Batchelors - Idyllic escape

Set in the grounds of a stunning 400 year old Tudor Hall and gardens, this beautiful new property is 1.5 miles away from the gorgeous Sissinghurst Castle Garden and within easy reach of Biddenden, with its renowned vineyard and Michelin starred restaurant. A perfect setting for couples, small families or friends. It has a very large open plan living/dining/kitchen area with doors onto a decked terrace and two en-suite double bedrooms, with ample room for parking.

Popular amenities for Maidstone District guesthouses

When is the best time to visit Maidstone District?

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Avg. price$222 NZD$220 NZD$229 NZD$234 NZD$247 NZD$241 NZD$241 NZD$243 NZD$241 NZD$240 NZD$229 NZD$225 NZD
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Quick stats about guesthouse rentals in Maidstone District

  • Total holiday rentals

    Explore 40 holiday rentals in Maidstone District

  • Nightly prices starting at

    Maidstone District holiday rentals start at $125 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,440 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Maidstone District holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Maidstone District rentals

  • 4.9 Average rating

    Maidstone District stays are highly rated by guests—averaging 4.9 out of 5!

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