Holiday houses in Chelsfield

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Top-rated holiday rentals in Chelsfield

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Guest favourite
The exterior of a brick building is shown, featuring three large windows arranged vertically, adorned with white fairy lights. A grey planter sits below one window, while a patterned stone pathway leads to the entrance.
Home in Crockenhill
4.81 out of 5 average rating, 138 reviews

Stunning 2 Bedroom house with parking

An Annexe of a larger property this is 2 Bedroom house fully equipped with all facilities. Two bedrooms both with double beds so the property sleeps 4 easily we also have a travel cot Central location near junction 3 of the M25 station is 10 minutes walk. Situated in the charming village of Crockenhill ,in the lovely kent countryside. nr to Brandshatch. Please note we only have a bath and hand held shower unit for washing hair The property has access to a stunning large garden. 1 parking space

Top Guest favourite
A well-maintained garden is framed by lush greenery, showcasing vibrant flower beds and neatly trimmed hedges. Beyond the garden, expansive views of rolling hills and the Darent Valley can be seen under a partly cloudy sky.
Condo in Otford
4.99 out of 5 average rating, 169 reviews

Amazing Views over Garden & Valley

Wake up & lift the automatic blinds directly from your SUPER KING SIZE BED & be captivated by the VIEW of the beautiful Darent Valley unfolding before you through the picture windows. SNUGGLE in a cosy armchair with a book, listen to your favourite music or EXPLORE many footpaths along the valley. Stroll through the fields to Otford & Shoreham villages, visit HISTORIC HOUSES & vineyards or simply stay at home & enjoy a spacious studio apartment whilst staring at the sunset with a glass of wine

Top Guest favourite
The exterior of a charming studio cottage is shown surrounded by lush greenery. A flowering wisteria drapes over one side, complementing the soft yellow walls. A stylish hanging chair is positioned on the lawn, providing a comfortable outdoor seating option.
Cottage in Meopham South
4.96 out of 5 average rating, 236 reviews

The Garden Room & parking - in the heart of Kent.

A Kentish gem - The Garden Room is an immaculately presented little cottage nestled in the beautiful hamlet of Harvel with thatched houses, Village Greens & the best Farm Café around. We offer a full range of in house Wellness Treatments. There is walking, stables, National Trusts, Silverhand Vineyard & Brands Hatch all on our doorstep. Good transport links; railway stations at Meopham, Borough Green & Ebbsfleet providing services DIRECT from London in UNDER 45 minutes. M25/M20 are close by.

Top Guest favourite
A cozy lounge area is featured with a spacious sofa and two modern armchairs arranged around a low wooden coffee table. A window allows natural light to brighten the space, while a decorative rug complements the wooden ceiling beams and gentle colour palette.
Cottage in Bromley
4.92 out of 5 average rating, 106 reviews

Gingerbread House in a quiet woodland setting

Gingerbread House is a self-contained annex set within the owners property, bordered by bluebell woodland and arable fields. The house is ideally situated for day trips into central London by train, many National Trust and English Heritage sites in Kent/Sussex, or events at Brands Hatch. The village of Pratts Bottom and the local pub is within a 10 minute walk. The nearest train stations are a 10 mins drive and offer fast services to London Charing Cross on the Tunbridge Wells/Hastings line.

Top Guest favourite
Two wooden lounge chairs are positioned on a stone patio, offering views of the expansive greenery and rolling hills in the distance. Lavender plants line the edge of the patio, enhancing the serene rural setting.
Cottage in Sevenoaks Weald
4.99 out of 5 average rating, 103 reviews

Quiet luxury rural cottage with fantastic views.

Rare, peaceful and spacious newly built cottage with private garden, comfortably sleeps 6. On Greensand AONB escarpment, with spectacular uninterrupted views over the Kent countryside. Rural retreat 2 miles south of Sevenoaks, half an hour by train to London Bridge. On private road. Own access and parking. New kitchen with light and airy dining and sitting area. WiFi. Very private south facing garden and patio. Fantastic walks to local pubs, national trust, great cycling. Use of tennis court.

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.
Condo in Wateringbury
4.99 out of 5 average rating, 279 reviews

Boutique country retreat, w/summerhouse 1hr London

Escape to the Kent countryside in this stylish, totally private apartment with your own courtyard garden and charming vintage summerhouse - perfect for relaxing weekend breaks just 1 hour from London. Ideal for couples looking for a peaceful countryside escape, offering rural views, countryside walks nearby and a local pub within a 12 min stroll. With self check in, parking and your own private entrance, it’s an easy base to unwind and explore Kent’s villages, vineyards and historic houses.

Top Guest favourite
The image captures an aerial view of a charming Tudor property surrounded by lush greenery. Two distinctive white-tipped oast houses are prominently displayed, along with neatly manicured gardens and open spaces. The serene countryside landscape extends into the background, showcasing rolling hills.
Home in Brasted
4.96 out of 5 average rating, 330 reviews

Oast Farmhouse, Ide Hill, Hever, Edenbridge

The Oast House is on a private Tudor Estate. A listed mid-Victorian property has charming period features, a large garden and storage. It theoretically sleeps 10 but suitable for 7 if one prefers sleeping alone. Terrific for group bookings, cycling and triathlon participants, temp workers, golfers, extended families in area for special occasions, corporate charity rides, or bake off weekends! Perfect for visiting Tudor England all around beautiful West Kent. We are 35 mins from South London

Top Guest favourite
A private garden area is presented, featuring a mix of stone and gravel pathways, surrounded by low-maintenance shrubs and plants. A comfortable lounge chair is positioned for relaxation, and outdoor lighting enhances the space. The entrance to the property is visible in the background.
Guest suite in Eynsford
4.99 out of 5 average rating, 149 reviews

Lullingstone Eynsford Annexe & Private Garden

Along the Darent Valley, minutes from M25 between Dartford and Sevenoaks (outside ULEZ 😁), surrounded by farmland and horses, we are a mile from Eynsford Village and train station. We have the Park and golf course as our back garden and The Roman Villa and Castle/World Gardens as our neighbours. Castle 'Lavender' Farm is a short walk too. Brands Hatch is a short drive. Parking on drive and private access to secure garden. 1 bedroom, bathroom, lounge, smart TV, DVD & fully equipped kitchen

Guest favourite
An open-plan living area is presented, featuring a circular dining table with modern chairs, a flat-screen TV on a white unit, and a comfortable sofa complemented by a side table. Natural light floods the space through large windows adorned with vertical blinds.
Apartment in Orpington
4.91 out of 5 average rating, 210 reviews

Spacious Cosy Modern Apartment in Greater London

*FLEXIBLE EARLY CHECK-IN AND LATE CHECK-OUT at no extra cost* A charming, modern, spacious, cosy 2-bedroom apartment for 4-5 guests, conveniently located in Orpington town centre. Only 7-9 mins walk away from Orpington train station (London fare Zone 6) with REGULAR TRAIN SERVICES INTO LONDON (17mins to London Bridge, 20mins to London Waterloo East, 27mins to Charing Cross). Ideal location for visiting London and travelling by car from EUROPE via DOVER (66 miles / 70 mins drive away).

Top Guest favourite
The spacious bedroom features a comfortable bed dressed in soft linens, flanked by bedside tables with lamps. Exposed wooden beams create a rustic ambiance, while patterned curtains frame the window. A wooden dresser adds character, and a full-length mirror reflects the room's charm.
Barn in Horley
4.94 out of 5 average rating, 529 reviews

Cosy, Rustic 17th Century Country Barn.

Charming 17th century Barn conversion. Restored with every attention to detail, abundance of character & exposed beams, fully equipped kitchen, attractive bathroom with roll top bath & rain shower. Underfloor heating, High Speed Wifi, Smart TV and optional hot tub (please enquire and book in advance). Just 14 minutes from Gatwick Airport/Station & the Express into London takes only 30 minutes, yet the Barn is set in open countryside, surrounded by fields, on an Equestrian property

Top Guest favourite
Guest suite in Brasted
4.95 out of 5 average rating, 109 reviews

Charming Guest Suite in the Kent Countryside

Our private annexe is nestled in a peaceful cul-de-sac, just 3 miles from Chartwell and 4 miles from Sevenoaks. London Bridge is a convenient 30-minute train ride away. Enjoy high-speed WiFi, HDTV, and a well-equipped bathroom. Refreshments like coffee, tea as well as an assortment of snacks are provided for our guests. The High Street, local pub, and shops are within walking distance. Guests can park their car on-site for free. EV charging available at extra cost.

Top Guest favourite
The interior features a vaulted ceiling with exposed wooden beams and intricate stained glass details. Natural light fills the space, highlighting the contrast between the rustic wood and modern design elements. A circular structure is visible, contributing to the open and airy atmosphere.
Barn in Plaxtol
4.97 out of 5 average rating, 158 reviews

Unique luxury self-contained oast house

Huge loft style Kentish roundel conversion. Situated on a farm set back from the road it is beautifully peaceful, with circular jacuzzi bath, projector, screen, all mod cons. Amazing walks & pubs from the doorstep, perfect for a country retreat, yet only 30 miles from London. Huge King size circular bed. Reynolds spa is 15 mins away. The house recently featured in Mr Bates v The Post Office, & the roundel was the actors green room.

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