Holiday houses in Maidstone District

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.

Location · Family · Backyard

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.

Location · Family · Comfort

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.

Family · Location · TV

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.

Family · Value · Walkability

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.

Value · Family · Amenities

The Bakers | Luxury Top-Floor Smart-Home Retreat

Luxury top-floor apartment set in the heart of the Kent countryside, designed for guests who value calm, quality, and effortless comfort. This bespoke open-plan retreat blends a refined interior with discreet smart-home technology, allowing seamless control of lighting and ambience via in-wall and desktop touchscreens. Immaculately prepared and peacefully private, it is ideal for couples or professionals seeking a quiet, well-cared-for escape. Not suitable for parties or gatherings.

Location · Value · Air conditioning

Bramley Shepherds Hut

Bramley Hut is a wonderful retreat with amazing views over the Weald of Kent. Immerse yourself in nature, a perfect hideaway for peace and relaxation. Located on a farm with apple orchards - hence the name Bramley Hut. Sit and enjoy wonderful sunsets with the best views in Kent. Bramley Shepherds Hut is a bespoke hut from the RHS approved Plankbridge Shepherds Hut Company. A newly planted wild flower meadow in front of the hut will be in flower during the summer months.

Location · Indoor spaces · Hospitality

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.

Location · Value · Parking

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.

Family · Location · Heating

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.

Value · Family · Kitchen

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.

Family · Location · View

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.

Value · Family · Solo travel