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
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, 220 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 charming exterior view of the property is featured, with a flowering wisteria vine cascading along the brick wall. The lawn stretches out, bordered by hedges and trees under a blue sky, creating a serene outdoor setting.
Home in Egerton
4.98 out of 5 average rating, 169 reviews

Little Appleby

Dog friendly Little Appleby is located in Egerton, rural Kent, the Garden of England. We are well placed for the tunnel with Folkestone, Le Shuttle 20 miles away. Egerton adjacent to Pluckley boasts many lovely country walks with huge Dering woods walkable from the listing and the villages of Goudhurst and Sissinghurst within 20 minutes. By car, Rye, Canterbury & Whitstable are within 40 minutes Ashford Designer outlet is 25 minutes away. The dog friendly restaurant and pub is a 5 minute walk.

Top guest favourite
A small wooden cabin is set against a backdrop of lush greenery and a clear blue sky. Several sheep graze peacefully in the vibrant green grass surrounding the cabin, with a wooden fence delineating the area.
Farm stay in Biddenden
4.97 out of 5 average rating, 304 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

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, 137 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 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, 103 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
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.
Apartment in Wateringbury
4.99 out of 5 average rating, 275 reviews

Peaceful, country views, garden, super king bed

Relax or work in this stylish apartment with private courtyard garden and vintage summerhouse * NO additional cleaning fee * 1st floor apartment with free parking * Private entrance * Country views * Wi-Fi * Self check in * 6ft super king bed * Heating * Smart TV * Plus a summerhouse * 1 hour train from London * Local pub/food 10 minute walk * Country walks * River 1 mile for boating/walks * Not suitable for pets or children * Please note EV charging is NOT permitted on the property*

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 Kent
4.97 out of 5 average rating, 150 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, 324 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
The historic windmill features a distinctive white weatherboard structure, surrounded by lush greenery. Two teak steamer chairs are positioned in the foreground, inviting relaxation in the garden. A clear blue sky with soft clouds enhances the serene rural setting.
Windmill in Benenden
4.99 out of 5 average rating, 837 reviews

Old Smock Windmill in rural Kent

Old Smock Mill is a romantic place for couples. The atmosphere inside is peaceful and relaxing. Everything is designed to unwind you from the moment you walk in. It is surrounded by the lovely Kent countryside where you can ramble and refresh yourselves by perhaps ending the day in one of the great pubs cosy by a log fire in Winter or in Summer in an English garden. Guests have said how hard it is to tear themselves away, it truly is a treasure to find.

Top guest favourite
A spacious living area showcases wooden beams and an open layout. A comfortable sofa faces a wood-burning stove, with a flat-screen TV nearby. The dining table is surrounded by woven chairs, and large windows provide natural light while offering views of the entrance and surrounding nature.
Cottage in Marden
4.99 out of 5 average rating, 594 reviews

The Lodge

**Opted in to Airbnb's enhanced cleaning protocol** Cosy barn-style accommodation nestled in the heart of the Kent countryside. Located close to National Trust sites and country walks. The Lodge is the perfect country getaway and romantic retreat. Please note this is strictly a NO SMOKING property inside the Lodge, the garden and surrounding field. The property is also NOT SUITABLE for infants, children or pets. Two adults only.

Top guest favourite
The exterior of a rustic barn highlights natural wood siding under a bright blue sky, accented by wispy clouds. A spacious lawn in front leads to a gravel driveway, with a view of the rolling countryside and distant hills visible in the background.
Guest house in Kent
4.98 out of 5 average rating, 109 reviews

Silverwood Studio Countryside Getaway

Escape to the countryside at Silverwood Studio, based on a farm in the most stunning location in Kent. We have recently renovated this barn to a high standard, complete with a log burner, kitchenette and a large picture window looking over the most fantastic view. It is located in a truly beautiful setting, in the middle of the English countryside, perfect for a romantic getaway or peaceful retreat.

Guest favourite
Cottage in Kent
4.9 out of 5 average rating, 111 reviews

The Clock House - a haven of tranquility!

In a rural setting, this beautiful converted property is surrounded by countryside and orchards. It sits in its own grounds of our house offering a haven of tranquility, but close to the village of Marden with a rail connection to London and just 20 mins from Tunbridge Wells with plenty of bars, restaurants and shops. Nearby attractions include Bewl Water, Bedgebury Pinetum and Hush Heath Vineyard.

Popular amenities for Maidstone District holiday rentals

When is the best time to visit Maidstone District?

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Frequently Asked Questions

  • 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.

  • 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!

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

    Four-legged friends are welcome in Maidstone District. Choose from more than 260 vacation rentals for guests traveling with pets.

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

    Maidstone District has more than 350 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do condo rentals in Maidstone District have wifi?

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

  • 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 470 vacation rentals in Bearsted, and over 50 vacation rentals in Snodland.

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

    Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with wifi, over 20 homes with free parking, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • 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 $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do tent rentals in Maidstone District have free parking?

    Absolutely! We offer over 10 tent rentals with free parking in Maidstone District. Enjoy a tailored experience with all the comforts you desire.

  • 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.

Quick stats about holiday rentals in Maidstone District

  • Total holiday rentals

    Explore 810 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 30,980 verified reviews to help you choose

  • Family-friendly holiday rentals

    350 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 260 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    370 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!

Destinations to explore

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