Guesthouse vacation rentals in Maidstone District

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Top-rated guesthouse rentals in Maidstone District

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Guest favorite
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 favorite
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, 262 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.

Top guest favorite
The Garden Studio is presented with large floor-to-ceiling windows featuring soft curtains. A wooden deck is adorned with a seating area, surrounded by manicured grass and flowering plants, offering a serene outdoor space for relaxation.
Guesthouse in Sissinghurst
4.93 out of 5 average rating, 183 reviews

Self Contained Garden Studio with stunning views

The Garden Studio has spectacular views over the Kent countryside from the property's floor to ceiling windows. The self contained compact studio has private access and includes lounge chairs, coffee table and a double bed. We have a dining table/ two stools overlooking the terrace. There is a fridge, a microwave, a two ring electric hob together with a kettle, Nespresso Coffee Machine and a toaster in the kitchen area. Iron/Board/Desk/Chair are on request prior to stay. Compact shower/wc.

Guest favorite
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

Guest favorite
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 favorite
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 favorite
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 favorite
A cozy sleeping area features a spacious bed with a patterned yellow throw and white linens. Warm green walls and soft lighting from two fixtures create a comfortable ambiance. A large mirror reflects the room, enhancing the sense of space.
Guesthouse in Kent
4.97 out of 5 average rating, 146 reviews

The Stables

Our one bedroom studio is the perfect retreat for two to relax and unwind.  Just a short walk from the tree lined high street of Tenterden, with it's eclectic mix of independent shops,  historic buildings and small cafes, it is also home to Kent & East Sussex's heritage steam railway. But if relaxing with your favourite glass is more your thing, then it's worth noting, that it is also in the centre of England's wine country, with our local vineyards - from Chapel Down to Gusbourne.

Top guest favorite
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 favorite
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 favorite
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, 298 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 favorite
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 guesthouse rentals

When is the best time to visit Maidstone District?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$25,940 GYDG$25,731 GYDG$26,777 GYDG$27,405 GYDG$28,869 GYDG$28,242 GYDG$28,242 GYDG$28,451 GYDG$28,242 GYDG$28,032 GYDG$26,777 GYDG$26,359 GYD
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Quick stats about guesthouse rentals in Maidstone District

  • Total vacation rentals

    Explore 40 vacation rentals in Maidstone District

  • Nightly prices starting at

    Maidstone District vacation rentals start at G$14,644 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,440 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Maidstone District vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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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