Family-friendly holiday rentals in Chislehurst

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Top-rated family-friendly rentals in Chislehurst

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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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
4.82 out of 5 average rating, 141 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.
Apartment in Otford
4.99 out of 5 average rating, 175 reviews

Stunning views with silent aircon!

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
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 Lullingstone
4.99 out of 5 average rating, 155 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 with short cut to train station less. The Park and golf course are our back garden and The Roman Villa and Castle/World Gardens our neighbours. Lavender Farm is a short walk too and Brands Hatch 10mins drive. Parking on drive and private access to secure garden. 1 bedroom, bathroom, lounge, smart TV, DVD & fully equipped kitchen

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 Greater London
4.93 out of 5 average rating, 110 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, 105 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
The exterior of Taylour House is showcased, highlighting its distinct Tudor-style architecture with wooden beams and red tiled roofs. Windows with leaded glass add to the historic charm, while a welcoming entrance is framed by a small overhang. The image captures the structure nestled in a quiet, inviting setting.
Home in Kent
4.98 out of 5 average rating, 101 reviews

Taylour House - Historic, unique, yet modern

Welcome to our historic 'hidden gem' Taylour House built in 1468 for the Lord Mayor of London. Quiet yet town centre location with local amenities on your doorstep. Easy reach of Central London, (Edenbridge Town station 10 mins walk) Gatwick and Heathrow. Sleeps up to 10 guests. Private dining by prior arrangement. Perfect for a holiday, family gatherings, birthday celebrations and hen/stag and bridal parties. Full refurbishment carried out in 2023. Children and dogs very welcome.

Superhost
A modern studio is set within a well-maintained garden, featuring a private outdoor deck with wooden railings. The entrance is framed by neatly trimmed shrubs, and large sliding doors provide a glimpse of the interior space, which is bright and welcoming.
Guest suite in Greater London
4.8 out of 5 average rating, 105 reviews

Garden gem: your private escape

Step into our cozy Chislehurst haven. Less than 45 mins from central London by public transport, our modern studio offers a private entrance, a comfy superking bed, a fully equipped kitchenette, self-contained toilet and shower room. Take a 5-min stroll to the charming village with shops and eateries. Explore London or venture into the beautiful Kent countryside. Ideal for two adults and can accommodate a child. Enjoy free roadside parking. Welcome to your retreat in the heart of SE London!

Top guest favourite
The exterior of the ground floor annex is shown, featuring a brick facade and a wooden framed window with multiple panes. A small bench is visible to the side, surrounded by a landscaped area with greenery.
Apartment in Eltham
4.92 out of 5 average rating, 340 reviews

1 bedroom Self contained flat in SE London near 02

Relax at this peaceful place to stay. Unique accommodation available perfect for an individual, couples, families or friends. Ground floor annex with private entrance. The property comprises of one bedroom which includes a King size bed, a single bed, wardrobes and a chest of draws. An en-suite shower room and private living room. There is a large sofa bed, table and 4 chairs. Also there is a small kitchen area. Wi-Fi and sky available Outdoor court yard includes dining table and chairs.

Superhost
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.
Flat in Greater London
4.91 out of 5 average rating, 213 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
Guest suite in Brasted
4.96 out of 5 average rating, 120 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.

Guest favourite
A couple relaxes in a bubbling outdoor hot tub, holding glasses, with a scenic view of lush green fields and trees in the background. A champagne bottle sits in an ice bucket beside them, enhancing the tranquil atmosphere.
Shepherd’s hut in Greater London
4.98 out of 5 average rating, 355 reviews

The Ultimate Couples Retreat | 30 Mins from London

This countryside retreat is the perfect romantic escape, just a 35 minute taxi/train ride minutes from London. Unwind in your private luxury hot tub, sip on a complimentary bottle Champagne under the stars, and wake up to breathtaking views of rolling fields and wildlife. Our handcrafted shepherd’s hut blends rustic charm with modern comfort, offering a king-sized stargazing bed, a cozy fire-lit deck, and a luxury bathroom, all set in a peaceful meadow.

Top guest favourite
Bungalow in Kent
4.97 out of 5 average rating, 103 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.

Popular amenities for Chislehurst family-friendly rentals

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Avg. price$290 SGD$287 SGD$276 SGD$333 SGD$338 SGD$306 SGD$309 SGD$282 SGD$268 SGD$277 SGD$272 SGD$301 SGD
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Quick stats about holiday rentals that are family-friendly in Chislehurst

  • Total holiday rentals

    Explore 50 holiday rentals in Chislehurst

  • Nightly prices starting at

    Chislehurst holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 700 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Chislehurst holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chislehurst rentals

  • 4.6 Average rating

    Chislehurst stays receive an average rating of 4.6 out of 5 from guests

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