
Guesthouse holiday rentals in Maidstone District
Find and book unique guesthouse rentals on Airbnb
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 $69 AUD per night before taxes and fees

Verified guest reviews
Over 3,860 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 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!
Top-rated Guesthouses in Maidstone District
Guests agree: These guesthouses are highly rated for location, cleanliness and more.

The Old Engineer, a rural boutique retreat
Escape to The Old Engineer, a peaceful boutique retreat for two in the Kent countryside, between Tunbridge Wells and Maidstone. Surrounded by fields, it has a private entrance, pretty courtyard garden and luxurious super-king bed (or twin beds on request). Enjoy a comfortable self-catering space, then explore nearby gardens, castles, vineyards, walking and cycling routes, country pubs and restaurants. The Gardens wedding venue and Tunbridge Wells are close by, with London just 50 mins by train.

Idyllic countryside annexe
Relax and unwind in this tranquil space, a short stroll to the charming high street of West Malling with its boutique shops, pubs and restaurants. The annexe is set in the grounds of our family home, overlooking gardens and fields of the Kent countryside. It has parking and its own separate entrance, accessed via a key box. The space is light and airy with a king size bed, table, sofa, living area, kitchenette and en-suite. Ideal for a couples retreat or to use as a base to explore the area.

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.

Kent home with a view
Annex at the bottom of our garden with its own patio area with views of the pool and garden. Nice quiet area with fields and woodland walks nearby Keys left in door - guests can let themselves in, we are generally around if you have questions There is BBQ area and a heated pool (shared with hosts) for stays of 2 days or more. Please note pool heating is not turned on until about mid-end of May and turned off in September. 5 min to Herne Bay. 15 min to Whitstable 20 min to Canterbury

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.

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.

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 Studio, Ticehurst
This fantastic open plan converted office space is located in the heart of High Weald, Area of Outstanding Natural Beauty. ‘The Studio’ is the perfect location for couples or families wanting to explore all that the countryside has to offer. Walking distance from Ticehurst Village, home to Sunday Times Pub of the Year ‘The Bell’. As well as Bewl water, Bedgebury Pinetum, fruit picking & plenty of National Trust properties on the doorstep, you won’t be short of things to do during your stay.

The Sauna House
Update! New Lino floor installed. Welcome to our luxurious Airbnb retreat, where relaxation meets sophistication. This elegant getaway, with no shared spaces, boasts an indoor oasis with a rejuvenating hot tub and a tranquil sauna, perfect for unwinding. A comfortable Silentnight mattress to relax. Step outside to our charming outdoor seating area, where you can sip your morning coffee or enjoy a glass of wine under the moonlight. This retreat is ideal for a couple seeking a romantic escape.

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.

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

Alpaca Lodge

'The Hideaway ' Sole Street, Cobham, Kent.

Converted Coach House in Kent

Woodsmoke Studio: Boho country retreat

Quaint rural 1-bedroom guest house with patio

Entire 1 bedroom Apt. Sleeps 4- Private Entrance!

Newly converted stable block

The Pheasant Roost
Guesthouses with a patio

Contemporary rural retreat with breathtaking views

The Den at Castle Lea

Double room in detached annex

Romantic, peaceful & beautiful Studio in Kent

Contemporary 1 bedroom Cabin with secluded Patio

Oak Tree Cottage

Converted forge with hot tub

The idyllic Acorn Lodge
Guest house rentals with a washing machine and dryer

The Outbuilding Appledore

The Annex

Stylish, Studio Apartment. 5 mins from Eurotunnel.

Watermill, beautiful village of Wye, North Downs

The Lodge

Converted stable block set in open farmland

Log cabin lakeside retreat in private grounds

Exclusive use modern barn with stunning views
When is the best time to visit Maidstone District?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $189 AUD | $186 AUD | $183 AUD | $218 AUD | $214 AUD | $208 AUD | $187 AUD | $189 AUD | $187 AUD | $175 AUD | $176 AUD | $196 AUD |
| 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 |
Destinations to explore
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