Holiday rentals in Maidstone District

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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
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, 515 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, 244 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
Farm stay in Biddenden
4.97 out of 5 average rating, 322 reviews

Ayleswade shepherd hut in Kent countyside

set in the small village of biddenden in the heart of the kent countryside belonging to a local farming family of many generations .You can expect beautiful country walks with many footpaths and local villages nearby for cream teas and lovely lunches , the nearby village of Headcorn with its straight connections to London or the coast is good for sightseeing, you wake up to views of our sheep and free range chicken and enjoy a relaxing cup of tea.Theres milk ,tea and coffee and our eggs for you

Guest favourite
Farm stay in Kent
4.92 out of 5 average rating, 148 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.

Superhost
A modern kitchen area features sleek dark cabinetry and stainless steel appliances, including an oven and microwave. Two pendant lights hang above a wooden bar with seating for two. A light gray sofa is positioned nearby, complemented by an orange decorative pillow.
Flat in Kent
4.88 out of 5 average rating, 132 reviews

The Bohemian Basement

The Bohemian Basement is a unique stylish one bed apartment with its own private garden in the heart of Maidstone. The apartment is 1 of 3 within a newly converted Victorian property just minutes walk from the town centres shops, restaurants and bars. Perfectly equipped with everything you’ll need while visiting Maidstone and with the added bonus of having a wonderful private outdoor garden space, makes this a fantastic Airbnb. There is free on street permit parking which we supply.

Top guest favourite
A single-story cottage is seen with a light grey exterior and a dark roof. Two large windows are featured at the front, allowing natural light inside. Potted plants adorn the entrance, and a gravel driveway provides access to the property. Lush trees are visible in the background.
Home in Lenham
4.96 out of 5 average rating, 188 reviews

Biggin Farm bungalow

Take a break and unwind in the beautiful kent countryside, but still have great access to road and rail networks. Only half a mile away is the newly opened Wishful Thinker pub and restaurant. 1mile away is the village of Lenham, the picturesque square has 2 public houses, a couple of restaurants and a tea room. Historic and beautiful Leeds castle is only 4 miles away and the city of Canterbury is 23miles. Lenham has rail link to London and Ashford. 4.5 miles to junction M20 junction 8.

Guest favourite
Cottage in Delting
4.86 out of 5 average rating, 202 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, 346 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, 225 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
4.96 out of 5 average rating, 127 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.

Top guest favourite
Bungalow in Kent
4.97 out of 5 average rating, 100 reviews

Luxury Spa Retreat: Sauna & Hot Tub

Escape to our exclusive gated spa retreat, nestled on 5.5 acres of serene countryside in picturesque Fawkham, Kent. This private and tranquil haven offers breathtaking views of rolling hills, perfect for relaxation. Unwind in the luxurious sauna, steam room, or hot tub, soaking in the peace after exploring local attractions. Just minutes from Brands Hatch, our retreat blends seclusion with convenience, your ultimate quiet getaway awaits.

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, 299 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.

Popular amenities for Maidstone District holiday rentals

When is the best time to visit Maidstone District?

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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 cabin rentals in Maidstone District?

    Experience the best of Maidstone District with our cabin rentals, starting at about $80 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!

  • Where should I stay in Maidstone District?

    Make yourself at home in Maidstone District by choosing from our most frequently booked neighborhoods. We have over 120 vacation rentals in East Farleigh, over 460 vacation rentals in Bearsted, and over 50 vacation rentals in Snodland.

  • 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 shepherds hut rentals in Maidstone District have a kitchen?

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

  • Do barn rentals in Maidstone District have wifi?

    Absolutely! We offer over 40 barn 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.

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 $25 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