Holiday rentals in Maidstone District

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Maidstone District

Guests agree: these stays 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
5 out of 5 average rating, 258 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
A light and airy living area is showcased, featuring a king-size bed with neatly arranged linens. A small dining table is positioned near a window, offering views of the outdoors. A sofa and kitchenette are visible, enhancing the space's functionality.
Guest house in West Malling
4.94 out of 5 average rating, 93 reviews

Idyllic countryside annexe

Relax and unwind in this tranquil space, a short stroll to the charming high street of West Malling with its boutique shops, pubs and restaurants. The annexe is set in the grounds of our family home, overlooking gardens and fields of the Kent countryside. It has parking and its own separate entrance, accessed via a key box. The space is light and airy with a king size bed, table, sofa, living area, kitchenette and en-suite. Ideal for a couples retreat or to use as a base to explore the area.

Guest favourite
Farm stay in Kent
4.92 out of 5 average rating, 155 reviews

Grand Bubble

Grand bubble sleeps 4 people who can enjoy the ultimate view of nature. You can fall asleep with the stars and wake up to the rising sun. This bubble has the wow factor and includes your own hot tub, BBQ, a shower, a flushing toilet, outdoor chess set and a golf buggy. The bubble is very secluded set at a bottom of a 12 acre field off a woodland. Out side of the bubble is a very large outdoor gazebo with comfy seating and a large gas bbq so even if it rains you can still bbq comfortably.

Top guest favourite
Cottage in Marden
4.97 out of 5 average rating, 32 reviews

Boutique Barn Retreat with Private Courtyard

Escape to this stylish boutique barn in the heart of the Kent countryside. Surrounded by orchards and countryside, Wagon Lodge blends rustic charm with modern comfort, featuring vaulted beamed ceilings, underfloor heating, a private courtyard for outdoor dining, and beautifully designed interiors for up to 4 guests. Perfect for romantic escapes, family getaways, vineyard visits, coastal adventures, and exploring nearby Rye, Goudhurst, Tunbridge Wells and Kent’s stunning castles & gardens.

Top guest favourite
Tiny home in Kent
5 out of 5 average rating, 71 reviews

Modern Detached Annexe

Recently renovated Annexe with private access No Smoking anywhere, vaping allowed in garden area Private courtyard garden & off road parking Easy access to motorway & rail links directly to London 15 minutes to Leeds Castle Ideal accommodation for anyone wanting to explore the local area or visiting relatives/working locally Ideal stopover for anyone travelling to or from Europe via Eurostar/Eurotunnel or Dover Port Hosts onsite should you need us but we do respect your privacy

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, 358 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
4.96 out of 5 average rating, 228 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.

Guest favourite
A modern kitchen space features minimalist cabinetry in light wood tones and a marble countertop. A dining table is set for four, with elegant place settings. The room is illuminated by suspended light fixtures, creating a warm ambiance. Graceful curtains frame a large window.
Barn in Kent
4.95 out of 5 average rating, 131 reviews

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.

Guest favourite
Home in Leeds
4.9 out of 5 average rating, 41 reviews

Lake House Staycation

Escape to The Lakehouse, a charming lakeside retreat steeped in history. Once a working quarry, the lake provided the very stone used to build this beautiful home—and even nearby Leeds Castle. Lovingly restored with original stonework, this tranquil hideaway offers stunning water views, modern comforts, and timeless character. Enjoy peaceful walks, local pubs, and the rolling Kent countryside—perfect for a romantic getaway or serene weekend escape.

Top guest favourite
A modern retreat structure features a covered outdoor area, showcasing a classic roll top bath and a seating area with a chair. Large glass doors open to the interior, complemented by decorative wall accents and greenery, with a natural landscape visible in the background.
Farm stay in Kent
4.96 out of 5 average rating, 99 reviews

Reeds retreat

welcome to Reeds Retreat , why not come and enjoy the lovely setting of this romantic spot in nature! Watch the wildlife while relaxing in the outside roll top bath or maybe spend the evening star gazing. Reeds retreat is the perfect space to unwind alone or with a special someone! Afternoon tea, with or without fizz can be added to your stay ! (On request) Pamper yourself during your stay, please feel free to enquire!

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.
Guest house in Kent
4.99 out of 5 average rating, 307 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.

Top guest favourite
The exterior of the studio is highlighted by a wooden deck area with turquoise chairs, accessed by a staircase. Lush greenery and flowering plants surround the entrance, while a gravel pathway leads to the studio. The historic Oast house is visible in the background.
Farm stay in Lenham
4.9 out of 5 average rating, 231 reviews

Home Farm Oast Studio

The Studio is in rural location in the garden of a historic Kentish Oast House with views across paddocks and woodland. It is situated above a barn style garage and is self contained with complete privacy. It has a Large bedroom, ensuite bathroom with shower, a modern fitted kitchen and has an outside wooden deck area with bistro table and chairs for your relaxation. Ideal for couples and business travellers. .

Popular amenities for Maidstone District holiday rentals

When is the best time to visit Maidstone District?

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Avg. price$191 SGD$189 SGD$189 SGD$189 SGD$195 SGD$200 SGD$202 SGD$208 SGD$195 SGD$186 SGD$178 SGD$200 SGD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Maidstone District?

    Maidstone District has more than 340 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Maidstone District with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Maidstone District?

    Four-legged friends are welcome in Maidstone District. Choose from more than 270 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Maidstone District?

    Yes! Work meets play with ease at over 360 vacation rentals in Maidstone District featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Maidstone District vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Maidstone District, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Maidstone District have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Maidstone District. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Maidstone District have a kitchen?

    Absolutely! We offer over 100 apartment rentals with a kitchen in Maidstone District. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Maidstone District have wifi?

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

  • Do apartment rentals in Maidstone District have free parking?

    Absolutely! We offer over 70 apartment rentals with free parking in Maidstone District. Enjoy a tailored experience with all the comforts you desire.

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

    Enhance your stay in our Farmstay Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Maidstone District

  • Total holiday rentals

    Explore 780 holiday rentals in Maidstone District

  • Nightly prices starting at

    Maidstone District holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 31,530 verified reviews to help you choose

  • Family-friendly holiday rentals

    340 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 270 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    360 properties have a dedicated workspace

  • Wifi availability

    710 of Maidstone District holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Maidstone District rentals

  • 4.8 Average rating

    Maidstone District stays are highly rated by guests – averaging 4.8 out of 5!

Destinations to explore

  1. Airbnb
  2. United Kingdom
  3. England
  4. Kent
  5. Maidstone District