
Holiday rentals in Maidstone
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Top-rated holiday rentals in Maidstone
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

Riverside Cottage , Maidstone
Open plan Luxury Cottage with balcony over looking the river and nearby lock. Traditional Barges moor along this part of the river. The Market town is a 20 minute walk along a picturesque tow path or a few minutes drive. There are several Bar/Restaurants a short walk away . Ideal area for all age groups. Comfortably furnished and well equipped. Four Lovely Bedrooms, two with original stone walls. Two Shower Ensuite's and a family Bathroom. Two outside courtyards and Plenty of parking.

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.

Peaceful, country views, garden, super king bed
Relax or work in this stylish apartment with private courtyard garden and vintage summerhouse * NO additional cleaning fee * 1st floor apartment with free parking * Private entrance * Country views * Wi-Fi * Self check in * 6ft super king bed * Heating * Smart TV * Plus a summerhouse * 1 hour train from London * Local pub/food 10 minute walk * Country walks * River 1 mile for boating/walks * Not suitable for pets or children * Please note EV charging is NOT permitted on the property*

The Bohemian Basement
The Bohemian Basement is a unique stylish one bed apartment with its own private garden in the heart of Maidstone. The apartment is 1 of 3 within a newly converted Victorian property just minutes walk from the town centres shops, restaurants and bars. Perfectly equipped with everything you’ll need while visiting Maidstone and with the added bonus of having a wonderful private outdoor garden space, makes this a fantastic Airbnb. There is free on street permit parking which we supply.

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.

Cottage in the Wood, Detling
'Cottage in the Wood' contains two double bedrooms one with en-suite bath/shower and one with shower room along with a sheltered hot tub taking advantage of the rolling Kent countryside with extensive views over the local Vineyards and North Downs beyond. The small and picturesque village of Detling is found on the slope of the North Downs, just northeast of Maidstone, and on the Pilgrims' Way - ideal if you're looking for a break only a short distance away from London.

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.

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.

Maidstone Bungalow sleeps 5 with parking
This stylish bungalow boasts with unique features and has everything you need for a comfortable stay. Open plan living space is airy and bright and compliments fully equipped modern kitchen. This 2 bed fully refurbished single level home sleeps up to 5 people and it can provide both king size and single beds. The bungalow is located in a prominent position in Allington, Maidstone, and it offers off road parking for multiple cars and a private garden.

Hermitage Cottage cosy 1-4 person accommodation.
Hermitage Cottage offers annexe accommodation. Bathed in sunshine in private garden setting. We are a commuters dream with Barming railway station at the door. London Victoria 57 minutes and Maidstone East just three minutes by rail. Fully fenced with garaging for one vehicle., entry by automatic gates. Finished to a very high standard with under floor heating and feature fire place. Your every comfort is assured. Welcome pack included.

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.
Popular amenities for Maidstone holiday rentals
Stay near Maidstone's top sights
Other great holiday rentals in Maidstone

Modern 2 Bed House in Rainham, Kent

Petite Gite in an idyllic cottage garden.

Gather&Unwind: Gardens, Woodland & Tennis Cottages

Cosy Rural Retreat with Log Burner

Stunning Views over Garden & Valley

Self-contained annex, with off-road parking.

Cosy Private Cottage in Wrotham, Kent Downs AONB

Idyllic countryside annexe
When is the best time to visit Maidstone?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $178 SGD | $182 SGD | $179 SGD | $187 SGD | $196 SGD | $201 SGD | $202 SGD | $211 SGD | $191 SGD | $183 SGD | $166 SGD | $185 SGD |
| 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 |
Frequently Asked Questions
What are the most popular amenities for Apartment Rentals in Maidstone?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 40 homes with free parking, over 70 homes with a kitchen, over 80 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Where should I stay in Maidstone?
Make yourself at home in Maidstone by choosing from our most frequently booked neighborhoods. We have over 120 vacation rentals in East Farleigh, over 350 vacation rentals in Weavering, and over 60 vacation rentals in Detling.
Do cottage rentals in Maidstone have a kitchen?
Absolutely! We offer over 10 cottage rentals with a kitchen in Maidstone. Enjoy a tailored experience with all the comforts you desire.
Do hotel rentals in Maidstone have free parking?
Absolutely! We offer over 20 hotel rentals with free parking in Maidstone. Enjoy a tailored experience with all the comforts you desire.
Are there hotel rentals with a dedicated workspace in Maidstone?
Yes! Work meets play with ease at over 20 hotel rentals in Maidstone featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly apartment rentals in Maidstone?
Four-legged friends are welcome in Maidstone. Choose from more than 10 apartment rentals for guests traveling with pets.
Are there family-friendly apartment rentals in Maidstone?
Maidstone has more than 20 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Maidstone?
Experience the best of Maidstone with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Quick stats about holiday rentals in Maidstone

Total holiday rentals
Explore 310 holiday rentals in Maidstone

Nightly prices starting at
Maidstone holiday rentals start at $25 SGD per night before taxes and fees

Verified guest reviews
Over 4,420 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wifi availability
290 of Maidstone holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Maidstone rentals

4.6 Average rating
Maidstone stays receive an average rating of 4.6 out of 5 from guests
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- Tower Bridge
- Big Ben
- Paddington
- British Museum
- Covent Garden
- Natural History Museum
- London Bridge
- Marble Arch
- Buckingham Palace
- Tottenham Court Road
- Hampstead Heath
- St Pancras International
- Kings Cross
- The O2
- Trafalgar Square
- Piccadilly Theatre
- Wembley Stadium
- Battersea Power Station (disused)
- ExCeL London
- Emirates Stadium
- Royal Albert Hall
- Olympia Events
- Russell Square
- Borough Market




