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
4.8 out of 5 average rating, 126 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, 145 reviews

Stunning 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

Guest favourite
The studio features a modern layout with a comfortable sofa in grey, accented by yellow cushions. A small dining table is positioned beside a kitchenette equipped with essential appliances. A TV is situated nearby, and natural light enters through a glass door leading to the patio.
Guesthouse in Greater London
4.97 out of 5 average rating, 61 reviews

Cosy Studio ‘Summer House’ South-East London

Individual entrance, kitchenette (no hob/oven), bathroom, sofa/double-bed, patio, large table, underfloor heating, blackout curtains. Chelsfield station 8 min walk, 30 min to London Bridge, ‘Oyster Card’ accepted. Next to the station is a nice British Pub/Restaurant and some small grocery stores. Our 'Summer House' is a proper Studio with everything you need for a short-term stay. We're a multinational family and love to travel. You'll stay in a quiet, friendly, and green part of Greater London.

Guest favourite
A cozy bedroom is presented with soft yellow tones and patterned bedding, creating a tranquil environment. A spacious bed is complemented by decorative pillows. Natural light filters through the large windows, dressed in light curtains, while a fan and a mirror are positioned nearby for comfort and convenience.
Guesthouse in New Addington
4.89 out of 5 average rating, 55 reviews

Annexe Haven Cosy Space with own (shower&entrance)

Escape at this unique and serene getaway. This stunning annex is an extension to the main property. This unique space boats of it's own private entrance with security night lights and it's own entrance to your private patio. Within the annex separate from the bedroom is a shower, a toilet and a sink. Also allocated in this space is your own hallway with fridge/freezer, a microwave and a kettle. The nicely designed bedroom is spacious with a smart tv & own private study & Free Netflix account.

Superhost
Apartment in Greater London
4.67 out of 5 average rating, 3 reviews

Palm Tree House | Candyland

Enjoy our brand-new, stylishly themed studio with a balcony in a building with an elevator. Modern furnishings include a fully equipped kitchen with a washing machine and dishwasher, a bathroom with shower, a Double bed, and a private balcony. Free Parking, super-fast Wi-Fi throughout, Smart TV are also available, access to a shared gym and workspace. It is just minutes from Orpington station, with easy access to London. Orpington Hospital and Shopping Centre are also within walking distance.

Top Guest favourite
A bright open-plan living area features two comfortable sofas, a coffee table, and a Smart TV. A wood-burning stove is centrally located, with a dining table and chairs nearby. A window allows natural light to illuminate the space, complemented by decorative artwork on the wall.
Home in Farningham
5 out of 5 average rating, 64 reviews

Converted barn in rural Kent

Whether you’re into motor racing, golf, cycling, long country walks or simply after some R&R, the Old Dairy Cottage is the perfect choice for a peaceful and serene retreat. The cottage is located in a rural hamlet, set amongst the beautiful Kent countryside (AONB). With miles of scenic walks and cycle routes on your doorstep plus Brands Hatch, London Golf Club, historic castles, English Heritage/National Trust sites, country parks, picturesque villages and much more all a short drive away.

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 Greater London
4.91 out of 5 average rating, 204 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).

Guest favourite
The exterior of a charming two-story cottage is shown, featuring a mix of stone and brick finishes. A pathway leads to the door, flanked by well-maintained greenery. Several large windows allow natural light, and the dual chimneys add character to the traditional design.
Cottage in Keston
5 out of 5 average rating, 16 reviews

Keston. Pretty Cottage, 2 double bedrooms and view

Overlooking Keston Common, quiet and set back from Commonside with parking to the front, two double bedrooms with first floor bathroom having separate shower and “egg bath”. Minimum 3 nights, discounts for weekly stay. Fully fitted kitchen with bay window & window seat overlooking the Common, open plan lounge with double doors to patio with swinging sofa and pretty back garden. Ground floor WC/utility room. Incredible holiday stay, easy transport to London, 40 mins drive to Gatwick.

Top Guest favourite
The kitchen features modern cabinetry with glass fronted shelves displaying various plates and glassware. A gas stove is positioned alongside an oven. Solid countertops provide ample workspace, with dual sinks under a window offering natural light and an outdoor view. Kitchen essentials are organized for convenience.
Guest suite in Chislehurst
4.92 out of 5 average rating, 104 reviews

One bedroom fully equipped flatlet

Located in beautiful wooded area on outskirts of London: 20 minutes by train to London Bridge. Chislehurst station 7 minutes walk, or 2 minutes bus ride. Village has "old" and "new" part with boutique restaurants & shops incl. supermarket (10-15 minutes walk ). Near the station are Chislehurst caves, restored historic monument & tourist attraction from war time use as a bomb shelter. Around the flat there are beautiful walks , runs & cycling in Petts Wood. House has quiet garden.

Top Guest favourite
A shepherd's hut is surrounded by a vibrant field of wildflowers, featuring bright red poppies. The structure has a classic design with a light door and a chimney visible atop the roof. Natural greenery frames the hut, creating a tranquil atmosphere.
Shepherd’s hut in Shoreham, Sevenoaks
5 out of 5 average rating, 24 reviews

Cosy shepherd’s hut with stunning valley views

Tucked away in the peaceful village of Shoreham, Sevenoaks, this cosy shepherd’s hut for two offers sweeping views of the Darenth Valley. Set in the grounds of a beautiful Grade II listed home, it’s fully equipped with a kitchenette, shower, toilet, basin, log burner as well as outdoor furniture to enjoy the view. With great local pubs, a vineyard, and walks nearby, and warm hosts on-site, this is the perfect spot to relax, recharge, and soak up the Kent countryside.

Top Guest favourite
An aerial view captures a serene retreat surrounded by lush greenery and mature trees. The single-story accommodation features a modest roof and large windows, inviting natural light into the interior. A gravel pathway leads through the landscape, enhancing the tranquil atmosphere.
Bungalow in Kent
4.96 out of 5 average rating, 82 reviews

Luxury Spa Retreat: Sauna, Steam & 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.

Guest favourite
The self-contained annex features a charming exterior adorned with lush green foliage, creating an inviting entrance. Large windows allow natural light to fill the living space, while the brick pathway leads up to the door, enhancing the property's connection to its surroundings.
Guesthouse in Kent
4.89 out of 5 average rating, 179 reviews

Beautifully developed historic stables, high spec

Professionally designed and newly developed self contained annex, part of a historic grade II listed building from the 17th century. Centrally located in Sevenoaks town, on the High Street, opposite Sevenoaks School and Knole Park National Trust site. Within the Kent Downs Area of Outstanding Natural Beauty (AONB). Private off-street parking and hot tub (both free of charge) and EV charging available. Pets welcome.

Popular amenities for Chelsfield holiday rentals

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