Holiday rentals in Maidstone District

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Maidstone District

  • Total holiday rentals

    Explore 800 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 33,190 verified reviews to help you choose

  • Family-friendly holiday rentals

    360 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 280 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    380 properties have a dedicated workspace

  • Wifi availability

    740 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!

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 modern countryside house features a striking angular design with large glass panels reflecting the sky. A spacious lawn surrounds the property, complemented by a patio and outdoor seating area. Lush greenery provides a natural border, enhancing the tranquil outdoor setting.
Barn in Sutton Valence
4.97 out of 5 average rating, 134 reviews

The Barnyard

Kick back and relax in this calm and stylish architecturally designed countryside home. Recently built, with the focus on creating a high end holiday home which has been equipped to a very high standard. Situated in the heart of the wine producing area of the Kent countryside, with many local pubs and restaurants only a gentle stroll away. The beautiful contemporary design, with vaulted ceilings and polished concrete floors serve to provide a relaxing and stylish vacation for up to six guests.

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, 264 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.

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, 137 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
The exterior of the farmhouse showcases a charming white facade with green trim. Quiet gardens filled with lush greenery and blooming flowers surround the building, providing a serene and inviting atmosphere. Large windows allow natural light to illuminate the interior spaces.
Home in Lenham
4.97 out of 5 average rating, 155 reviews

Farmhouse 4 posters cinema music room AGA kitchen

Chilston Home Farm is a period farmhouse in the middle of Kent, the Garden of England. We have lovely walks right from the door, it's perfect for exploring historic Kent and there's easy access to trains to London & Europe. You’ll love the period ambiance: the kitchen Aga, cosy log fires. Two of the bedrooms have king-size four-posters. There's even a bijou cinema! Lots of books & games, a piano, guitar & drums for music lovers, pool table & darts. Ideal for couples or larger families.

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, 365 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, 230 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 shepherd's hut is illuminated by warm outdoor lights against a twilight backdrop. A fire pit with a bright flame is surrounded by log seating, offering a cozy gathering space. A small table and chairs are positioned nearby, completing the inviting outdoor area.
Shepherd’s hut in Kent
4.91 out of 5 average rating, 574 reviews

Shepherds hut

Handcrafted Hop pickers shepherds hut perfect for either a romantic break or a well deserved escape from the bustle of life. Experience nature in luxury, sit in your hot tub and enjoy the views and country living. You are in your own private space. You have full use of your own private hot tub. The shepherds hut has a inside kitchenette, bathroom, a full size double bed and log burner. Outside has a charcoal BBQ, fire pit, lay z spa hot tub and seating area.

Top guest favourite
A dining table is set with homemade bread and refreshments, positioned near a window that offers a view of rolling fields. Outside, a group of alpacas stands by a wooden fence, surrounded by green grass and trees.
Barn in Kent
4.96 out of 5 average rating, 218 reviews

North Downs Cottage: Hot Tub, Alpacas & Charm

🛁 Birch Cottage: Hot Tub & Alpaca Views Welcome to Birch Cottage, a beautiful holiday home in the village of Harrietsham, at the foot of the North Downs. Enjoy your private, wood-fired hot tub and the surrounding outstanding views. Located on a working smallholding, you'll meet our resident alpacas, pigs, and sheep (like Bam!) and our goose, Meggi. Perfect for wildlife lovers and those seeking fantastic country walks. A unique, tranquil retreat awaits!

Guest favourite
Home in Leeds
4.92 out of 5 average rating, 48 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.

Guest favourite
Home in Kent
4.91 out of 5 average rating, 328 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
Bungalow in Kent
4.97 out of 5 average rating, 105 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 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
4.95 out of 5 average rating, 103 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!

Popular amenities for Maidstone District holiday rentals

When is the best time to visit Maidstone District?

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Avg. price$191 SGD$188 SGD$188 SGD$188 SGD$195 SGD$200 SGD$201 SGD$208 SGD$195 SGD$186 SGD$178 SGD$200 SGD
Avg. temp5°C5°C7°C10°C13°C16°C18°C18°C15°C12°C8°C6°C

Frequently Asked Questions

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

    Maidstone District has more than 360 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Maidstone District with our private suite rentals, starting at about $90 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 280 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 380 vacation rentals in Maidstone District featuring dedicated workspaces. Stay connected and productive in your home away from home.

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

    Yes! Dive into the perfect getaway at one of over 10 cottage rentals with pools in Maidstone District, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in Maidstone District have air conditioning?

    Absolutely! We offer over 10 apartment 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 20 shepherds hut rentals with a kitchen in Maidstone District. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Maidstone District have wifi?

    Absolutely! We offer over 90 cottage rentals with wifi in Maidstone District. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Maidstone District have free parking?

    Absolutely! We offer over 30 guesthouse rentals with free parking in Maidstone District. Enjoy a tailored experience with all the comforts you desire.

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

    Enhance your stay in our Barn Rentals with the most popular amenities: over 30 homes with free parking, over 30 homes with wifi, over 30 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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