
Holiday rentals in Maidstone
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Top-rated holiday rentals in Maidstone
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Romantic Hideaway & Hot tub in Kent Countryside.
A Unique Garden House in the heart of the Kent Countryside with views across our 3 acre orchard. Included in your stay is your very own private garden, complete with hot tub & summerhouse to relax in. The property also has private parking plus a secret woodland hideaway. Within walking distance is both Sharsted Wood and Doddington Place Gardens which are great for exploring, plus our local pubs - The Black Lion and The Chequers Inn which are perfect for a spot of lunch or a dinner reservation.

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.

Boutique country retreat, w/summerhouse 1hr London
Escape to the Kent countryside in this stylish, totally private apartment with your own courtyard garden and charming vintage summerhouse - perfect for relaxing weekend breaks just 1 hour from London. Ideal for couples looking for a peaceful countryside escape, offering rural views, countryside walks nearby and a local pub within a 12 min stroll. With self check in, parking and your own private entrance, it’s an easy base to unwind and explore Kent’s villages, vineyards and historic houses.

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.

Petite Gite in an idyllic cottage garden.
Come and make yourself at home in this unique hand crafted miniature gite. Tucked away in the garden of a Tudor cottage, situated on the Addington village green just yards from the Angel Inn. Cottage style Kitchenette with miniature Belfast sink and cupboards. Small double raised bed with storage and dining table underneath. Fully centrally heated for those cosy winter/autumnal days. Rose Cottage, as we call it, has been painstakingly restored to create a delightful, light and cosy 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.

Acorn Lodge @ The Oaks Retreat
This memorable place is anything but ordinary. It is The Oaks Retreat, WINNER of the Paris Design awards 2024 'best hospitality interior', an architecturally inspired bespoke woodland Airbnb located in the seaside town of Whitstable. The Acorn Lodge is a bespoke 1 king size bedroom retreat fully customized with high-end finishes. It must be seen in person to be fully appreciated. Our Wellness area is equipped with a log sauna, a cold plunge and outdoor shower.

Old Smock Windmill in rural Kent
Old Smock Mill is a romantic place for couples. The atmosphere inside is peaceful and relaxing. Everything is designed to unwind you from the moment you walk in. It is surrounded by the lovely Kent countryside where you can ramble and refresh yourselves by perhaps ending the day in one of the great pubs cosy by a log fire in Winter or in Summer in an English garden. Guests have said how hard it is to tear themselves away, it truly is a treasure to find.

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.

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

Minty the green bus conversion

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Rosemary Cottage: Gardens, Woodland & Tennis

St Faiths Chambers Ground floor Apartment

A luxurious country retreat with Jacuzzi hot tub

Countryside luxury family dog friendly cottage

The Roost Group - 2 Bed Riverside Apartment No.4
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 | $186 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 best places to stay in Maidstone?
Central Maidstone neighborhoods have convenient access to shops, dining, and riverside walks, while nearby villages provide quieter, scenic stays. Both options make it easy to explore the area's history and parks.
What are the best things to do in Maidstone with kids?
Children often enjoy exploring Maidstone's parks, botanical gardens, and interactive museums. Many families spend time at animal centers or participating in outdoor adventure activities.
What are some of the best things to do in Maidstone?
Explore castles, stroll riverside parks, and visit museums that highlight local heritage. Many visitors enjoy discovering gardens and sampling Kentish cuisine at local markets or cafés.
How is the weather in Maidstone?
Maidstone has cool winters around 36–47°F (2–9°C) with occasional rain and milder summers averaging 55–73°F (13–23°C). Light layers and a waterproof jacket make it easier to adjust to changeable weather throughout the year.
When is the best time to visit Maidstone?
Late spring through early autumn is frequently suggested for milder weather and an active events calendar. These months highlight blooming gardens and outdoor activities across Maidstone.
What are the best places to visit in Maidstone?
Popular places to visit include Leeds Castle, Mote Park, and the Maidstone Museum. Historic estates and tranquil gardens are also often recommended for a balanced visit.
What are some hiking trails in Maidstone?
Maidstone has walking paths along the River Medway, and nearby woodlands with marked trails suitable for various fitness levels. Parks and nature reserves around the area can be a good starting point for local hikes.
What are some family activities we can do in Maidstone?
Families often explore animal parks, hands-on museums, and play areas in Maidstone’s parks. Cycle paths and activity centers around the area provide active ways to spend the day together.
What are some of the best day trip ideas from Maidstone?
Consider exploring Kentish villages, coastal towns, or historic market areas around Maidstone. Vineyards and walking trails in the surrounding countryside are frequently suggested as day trips.
Are there any pet friendly accommodations available in Maidstone?
Pet friendly accommodations are available in various parts of Maidstone, including both town and countryside settings. Parks and riverside walks make it an enjoyable place to travel with pets.
What are some local tips for visiting Maidstone?
Explore river paths and parks around the town center, and consider local markets for regional products. Comfortable shoes are helpful, as Maidstone has several historic sites and gardens best enjoyed on foot.
What is Maidstone known for?
Maidstone is known for its historic castles, riverside walks, and vibrant local markets. The area has connections to the hop-growing traditions of the Kent countryside.
What are the best hidden gems to explore in Maidstone?
Smaller museums, independent art spaces, and riverside parks are often mentioned as hidden gems in Maidstone. The nearby countryside has quiet woodlands and nature areas for a peaceful outing.
What are the best foods to try in Maidstone?
Maidstone has dishes featuring locally grown produce, traditional Kentish pies, and artisan ciders. You may also find regional cheeses and baked treats at farmers’ markets or local bakeries.
What should I bring for a trip to Maidstone?
Pack comfortable walking shoes, a waterproof jacket, and adaptable layers to match variable temperatures. A reusable water bottle and a small daypack are helpful for exploring parks and historic sites.
What is the nightlife in Maidstone like?
Maidstone’s nightlife scene includes lively pubs, bars, live music venues, and periodic seasonal events. Locals often gather in the town center and along the riverside for entertainment.
What are the most popular events or festivals in Maidstone?
Maidstone often hosts food and drink festivals, live music celebrations, and agricultural shows, especially in warmer months. The area is also known for recurring cultural events and seasonal fairs.
Are there family friendly vacation rentals in Maidstone?
Family friendly vacation rentals can be found across Maidstone, with a mix of neighborhoods and rural surroundings. Many homes have features such as gardens or extra rooms tailored for group stays.
Quick stats about holiday rentals in Maidstone

Total holiday rentals
Explore 300 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 4,450 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
160 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

4.7 Average rating
Maidstone stays receive an average rating of 4.7 out of 5 from guests
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- Paddington
- British Museum
- Covent Garden
- St Pancras International
- Hampstead Heath
- London Bridge
- Buckingham Palace
- Wembley Stadium
- Kings Cross
- Big Ben
- The O2
- Tower Bridge
- Marble Arch
- Tottenham Court Road
- Natural History Museum
- Trafalgar Square
- Piccadilly Theatre
- ExCeL London
- Emirates Stadium
- Battersea Power Station (disused)
- Royal Albert Hall
- Russell Square
- Olympia Events
- Borough Market




