Holiday rentals in Maidstone

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Top-rated holiday rentals in Maidstone

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Top guest favourite
A close-up of a wooden tray features two elegant champagne flutes alongside a bottle of Taittinger champagne. Fresh rose petals are scattered on the tray, with a bubbling hot tub visible in the background.
Place to stay in Lynsted
5 out of 5 average rating, 512 reviews

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.

Top guest favourite
The entrance to The Annex features a well-defined porch with a welcoming door. Flower pots with red blooms sit on either side of the entrance, while a gravel pathway leads up to the front, framed by greenery from nearby plants.
Home in Leeds
5 out of 5 average rating, 239 reviews

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.

Top guest favourite
An open plan living area features a circular wooden table surrounded by teal chairs and a cozy seating arrangement with a leather sofa and armchair. A television is positioned beside a decorative fireplace, while natural light filters in through windows overlooking lush greenery.
Apartment in Wateringbury
4.99 out of 5 average rating, 282 reviews

Romantic country retreat, with garden summerhouse

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.

Guest favourite
An aerial view of a unique bubble lodging situated on a grassy area surrounded by trees in bloom. Nearby, a wood-burning hot tub and seating area are visible, offering an inviting outdoor space for relaxation.
Farm stay in Harrietsham
4.96 out of 5 average rating, 225 reviews

Wooded Bubble tent

Located on a 120 acre farm. The ultimate star gazing pad. The unusual lodging is fully equipped to help you enjoy a excellent and original night. A cosy bed, a toilet, shower, clean towels and a thousand stars over you. Lay in bed turn off the lamps and start counting. Enjoy a relaxing wood burning hot tub with a glass of prosecco, inhale a breath of fresh air and lay back and enjoy the views of the North downs. Tap onto my profile picture see my other bubbles. Not suitable for under 4 years.

Top guest favourite
The exterior of a stone cottage is presented, featuring a balcony with a glass railing overlooking the river. Lush greenery surrounds the property, with a wooden jetty in the foreground, adding to the tranquil riverside setting.
Home in Sandling
4.99 out of 5 average rating, 193 reviews

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.

Top guest favourite
A quaint entrance is framed by a variety of colorful flowers, including pink and purple blooms, cascading from hanging baskets and garden beds. The rustic wooden door is set against a whitewashed wall, complementing the charming brick pathway leading up to it.
Place to stay in Addington
4.98 out of 5 average rating, 242 reviews

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.

Guest favourite
A historic stone bridge spans a flowing river, showcasing several arches with water rushing beneath. Lush greenery flanks both sides of the river, adding to the serene natural landscape in the background.
Apartment in Yalding
4.84 out of 5 average rating, 126 reviews

Beautiful 2 Bedroom Apartment

Recently renovated listed 2 bedroom first floor apartment. Large modern well equipped kitchen with breakfast bar. Living room with sofas, bean bags electric fire and large television. 2 bedrooms, one double one twin. Beautiful bathroom with roll top bath. Set in the rolling Kent country side perfect for an action packed weekend away with the kids, seeing friends and family or a sophisticated few nights away with friends. Perfect for friends, families or contractors.

Guest favourite
A charming cottage exterior is framed by lush greenery and mature trees. The building features a traditional wooden door and a large window, allowing natural light to fill the interior. Gravel pathways lead to the entrance, enhancing the rustic appeal of the setting.
Cottage in Delting
4.86 out of 5 average rating, 201 reviews

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.​

Top guest favourite
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.
Guest house in Boughton Monchelsea
4.97 out of 5 average rating, 343 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.

Guest favourite
A well-lit bedroom features a spacious bed with a combination of white and orange bedding. Two framed artworks are mounted on the wall above the headboard. Natural light streams in from a large window, which offers a view of the surrounding area.
Bungalow in Kent
4.97 out of 5 average rating, 124 reviews

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.

Guest favourite
Double doors open to a private garden highlighting a well-maintained lawn and patio area. A circular table with ornate chairs is positioned centrally, and a barbecue station is visible in the background. The scene is illuminated by natural sunlight.
Home in Kent
4.91 out of 5 average rating, 312 reviews

Hermitage Cottage 2 Guests 2 Children.

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.

Top guest favourite
A summer house is set amidst lush greenery, featuring large windows that invite natural light. A small patio area is visible, adorned with a table. The structure is surrounded by trees, creating a serene natural setting.
Tiny home in Goudhurst
4.94 out of 5 average rating, 281 reviews

Summer House

Set in a picturesque village with miles of country walks, this detached Summer House is located just a few minutes walk from the village centre where you will find a local pub, tea rooms and village store. From its position you will enjoy beautiful views of rolling countryside and access to various walks on your doorstep. There are several National Trust places close by like Sissinghurst and Scotney Castle.

Popular amenities for Maidstone holiday rentals

When is the best time to visit Maidstone?

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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 $26 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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  5. Maidstone