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.

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Top guest favourite
A modern dining area features a round table set with plates and flowers, surrounded by four black chairs. A cozy sofa is positioned nearby, with a soft color palette complementing the overall design. Light enters through an opening to the kitchen area.
Home in Rainham Mark
4.97 out of 5 average rating, 136 reviews

Modern 2 Bed House in Rainham, Kent

Welcome to this modern home from home in Rainham. Perfect for any stay - leisure, work, visiting family/friends & local attractions. Conveniently situated close to local amenities, 5-minute walk to train station and town centre, restaurants, pubs, bars, shops & more. Including 2 spacious bedrooms with double & king size bed, new luxury bathroom & open lounge with all Virgin TV channels including Sky Sports & Netflix, fully equipped modern kitchen, large garden & a parking space for your stay.

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, 199 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.
Guest house in Sittingbourne
4.94 out of 5 average rating, 264 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
A warm log-burning stove is seen with two glasses and a bottle of sparkling wine on a table nearby. Through a large window, natural light streams into the space, highlighting the wooden exterior of the lodge.
Serviced apartment in Pluckley
4.97 out of 5 average rating, 127 reviews

The Bamboo Lodge studio B&B in lovely countryside

The Bamboo Lodge is a new, comfortable, modern self-contained studio available on a self-catered or B&B basis. Features: - detached accommodation with private entrance - fully equipped separate kitchen (inc dishwasher) - en suite shower room - king size bed (John Lewis natural collection) - duck down duvet & pillows - high quality cotton bed linen & towels - log burning stove & comfortable seating area - peaceful location with off-road parking - easy access from M20 & A20 (great stop-over)

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, 185 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
The exterior of the Strawberry Barn features a green wooden facade, surrounded by lush foliage. A small patio with a bistro table and two chairs provides a space to enjoy the outdoor view. The entrance door is framed by blooming red and green plants.
Guest house in Kingswood
4.97 out of 5 average rating, 100 reviews

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.

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, 230 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 spacious sleeping area is featured with a black metal bed frame, soft-textured pillows, and a bright yellow throw draped over the bed. The wall behind is adorned with a mural of trees, complemented by a wooden chest of drawers and dark curtains.
Home in Cliffe
4.95 out of 5 average rating, 167 reviews

Cosy 1 bed countryside cottage, tranquil location

Very spacious 1 bed en-suite cottage with off road parking and a small courtyard area. Formerly an Annex to the main house it is ideally situated for walking/hiking with easy access to the RSPB marshes of Cliffe. Beautiful views of the Kent countryside leading to Cooling Castle Barn, St Helens Church, Cliffe and St James church which inspired Charles Dickens to write Great Expectations where the hero Pip met Magwitch the convict. Easy car access to Historic Rochester Castle and Cathedral.

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.
Guest house in Tonbridge
4.97 out of 5 average rating, 315 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 open-plan living area showcases warm wooden beams and a spacious layout. A comfortable light-colored sofa and ottoman are placed adjacent to a dining table, while a well-equipped kitchen is visible in the background. Fresh flowers accent the dining table, adding subtle elegance.
Guest house in Kings Hill
4.96 out of 5 average rating, 279 reviews

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.

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, 302 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.

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, 268 reviews

Peaceful, country 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*

Popular amenities for Maidstone holiday rentals

When is the best time to visit Maidstone?

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Avg. price$182 SGD$185 SGD$183 SGD$191 SGD$200 SGD$205 SGD$206 SGD$215 SGD$195 SGD$167 SGD$172 SGD$184 SGD
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Frequently Asked Questions

  • What are the most popular amenities for House Rentals in Maidstone?

    Enhance your stay in our House Rentals with the most popular amenities: over 110 homes with wifi, over 90 homes with free parking, over 110 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • What types of vacation rentals are available in Maidstone?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Maidstone. From over 120 house rentals to over 80 apartment rentals, we've got you covered.

  • 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 280 vacation rentals in Penenden Heath, and over 60 vacation rentals in Detling.

  • Do condo rentals in Maidstone have a kitchen?

    Absolutely! We offer over 10 condo rentals with a kitchen in Maidstone. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Maidstone have free parking?

    Absolutely! We offer over 40 apartment rentals with free parking in Maidstone. Enjoy a tailored experience with all the comforts you desire.

  • Are there house rentals with a dedicated workspace in Maidstone?

    Yes! Work meets play with ease at over 50 house rentals in Maidstone featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly house rentals in Maidstone?

    Four-legged friends are welcome in Maidstone. Choose from more than 20 house rentals for guests traveling with pets.

  • Are there family-friendly house rentals in Maidstone?

    Maidstone has more than 70 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cottage rentals in Maidstone?

    Experience the best of Maidstone with our cottage rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do hotel rentals in Maidstone have wifi?

    Absolutely! We offer over 20 hotel rentals with wifi in Maidstone. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Maidstone

  • Total holiday rentals

    Explore 290 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 4,150 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

    270 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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