Family-friendly vacation rentals in Maidstone

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Top-rated family-friendly rentals in Maidstone

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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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
4.99 out of 5 average rating, 190 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
The exterior of the annex is showcased, featuring vertical wooden slats and a glass-paneled door. A small window is visible, allowing natural light into the space. The entrance is set on a paved path, surrounded by greenery and a water storage tank nearby.
Guesthouse in Sittingbourne
4.93 out of 5 average rating, 260 reviews

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.

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 Allington
4.99 out of 5 average rating, 184 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 rustic home is surrounded by lush greenery, with a spacious garden inviting relaxation. The exterior features a warm color palette, complemented by large windows and a welcoming terrace that provides access to the garden.
Barn in Kent
4.95 out of 5 average rating, 140 reviews

Sissinghurst Stables in the Garden of England.

Sit and enjoy the large private garden from the sunny south -facing terrace. This rustic home has an authentic feel, with a quirky calming country design, interspersed with antique furniture and botanical artwork throughout. There is a separate TV room and magical mezzanine play area with baskets of toys for children. There is a private, sunny, nature filled garden. Only one hour from London by train which makes it a perfect location for a city trip too. Insta: Sissinghurst_stables_airbnb

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, 229 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.

Top guest favourite
A charming outdoor seating area features white metal chairs and a small table set on wooden decking. Potted plants flank the seating arrangement, and a brick wall provides a backdrop. The space is bordered by lush greenery, offering a serene environment.
Guesthouse in Tonbridge
4.97 out of 5 average rating, 313 reviews

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

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.
Guesthouse in Boughton Monchelsea
4.97 out of 5 average rating, 296 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
The exterior of the lodge showcases a modern structure with dark wood siding, complemented by multiple large windows. Sunlight filters through the trees, illuminating the gravel parking area in front. A inviting entrance can be seen leading into the accommodation.
Cottage in Kent
4.97 out of 5 average rating, 211 reviews

Northdown Lodge

We are a unique rural modern lodge with every luxury, nestled in 3 acres. Beautiful views and walking on the Northdown's way. Great local pubs to enjoy. No better place to relax and unwind watching amazing sunsets, and perhaps sampling our local wine grown next door. Or put your feet up by the log burner and watch a film from our vast collection, perhaps with a homemade afternoon tea (available to book in advance). Whatever your preference, you wont be disappointed.

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.
Guest suite in Wateringbury
4.99 out of 5 average rating, 265 reviews

Peaceful apt, views, garden, WiFi & sunsets

Relax or work in this stylish apartment with private courtyard garden and vintage summerhouse * First floor apartment with free parking * Country views * Wi-Fi * Self check in * 6ft super king bed * Heating * Smart TV * Plus a summerhouse * Under 1 hour train from London * Local pub/food 10 minute walk * Close to country walks * River Medway 1 mile for boating/walks * Not suitable for pets or children * Please note EV charging is NOT permitted on the property*

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.
Place to stay in Goudhurst
4.93 out of 5 average rating, 222 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 room, village store and Italian delicatessen . From its position you will enjoy beautiful views of rolling countryside and access to walks on your doorstep, as well as several National Trust places like Sissinghurst and Scotney Castle close by.

Top guest favourite
A spacious room features a super king bed adorned with crisp white linens, flanked by bedside tables with floral lamps. A comfortable sofa in a muted blue hue is positioned in front, inviting relaxation. Natural light enters through a window, illuminating the warm wooden flooring.
Guesthouse in Kent
4.99 out of 5 average rating, 295 reviews

The Old Engineer, a rural boutique retreat

Our rural boutique accommodation with private entrance and pretty courtyard garden is surrounded by fields. The space is designed with the guests comfort and luxury in mind. It is the perfect spot for a relaxing and peaceful get away. Super king bed (or twin if requested). Located between Tunbridge Wells and Maidstone, close to the Hop Farm and attractions such as Sissinghurst Gardens, Vineyards and many NT properties.

Guest favourite
The open-plan lounge features a vaulted ceiling and is furnished with a spacious light grey sofa, complemented by decorative cushions. A flat-screen TV is positioned on a white media console, with a log burner highlighted beside it. Natural light enters through the window, adorned with simple blinds.
Cabin in Penenden Heath
4.86 out of 5 average rating, 366 reviews

The Heath large log cabin Maidstone

Large detached one bedroom log cabin with open plan kitchen/lounge which has a vaulted ceiling. Has its own side entrance and is totally separate from the main house. We also have off street parking for 1 car. Ideal if you want to get away from it all for a few days or weeks. Located 2 minutes from J7 M20 close to Maidstone. Ideal for Leeds Castle. The Kent show ground. and Kent life. The Maidstone studios.

Popular amenities for Maidstone family-friendly rentals

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Avg. price$232 CAD$233 CAD$235 CAD$253 CAD$249 CAD$259 CAD$252 CAD$256 CAD$261 CAD$243 CAD$225 CAD$246 CAD
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Quick stats about vacation rentals that are family-friendly in Maidstone

  • Total vacation rentals

    Explore 110 vacation rentals in Maidstone

  • Nightly prices starting at

    Maidstone vacation rentals start at $42 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,590 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    110 of Maidstone vacation 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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