
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.

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.

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.

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

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.

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.

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.

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

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.

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.

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.

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.

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
Family-Friendly guesthouses

Converted Coach House in Kent

Kentish country side, Hot tub, great outside space

The idyllic Acorn Lodge

Former Game keepers lodge with woodburner

Cosy cabin retreat

Alpaca Lodge

The Dragons Nest

Little Culvers
Guesthouses with a patio

Barons Granary, The Bull Pen, Iden nr Rye

Detached garden annex in Lewes

Oak Tree Cottage

Stylish one-bedroom studio in Appledore, Kent

Amazing Clockhouse in a perfect location

The Secret Hideaway (SS6)

Unique Cabin Retreat in an Urban Green Oasis

The Haven
Guest house rentals with a washing machine and dryer

Whispering Waves-Brighton 8 mins/ Beach/AC/Parking

Exclusive use modern barn with stunning views

Watermill, beautiful village of Wye, North Downs

Self Contained Garden Studio near Glyndebourne

Stylish, Studio Apartment. 5 mins from Eurotunnel.

The Annex

Rustic Log Cabin, quiet with uninterrupted views

Private Studio flat in Ditchling
When is the best time to visit Maidstone District?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $214 NZD | $213 NZD | $221 NZD | $226 NZD | $239 NZD | $233 NZD | $233 NZD | $235 NZD | $233 NZD | $232 NZD | $221 NZD | $218 NZD |
| Avg. temp | 5°C | 5°C | 7°C | 10°C | 13°C | 16°C | 18°C | 18°C | 15°C | 12°C | 8°C | 6°C |
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 $121 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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