Holiday houses in Orpington

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Top-rated holiday rentals in Orpington

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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, 160 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

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
4.92 out of 5 average rating, 105 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
Home in Greater London
5 out of 5 average rating, 10 reviews

School Cottage conversion

School cottages converted to a high quality luxury specification. Two bedroom, two bathrooms found up a spiral stairwell above a beautifully designed open area including a modern kitchen and living area. A unique and beautiful property, lived in with all the appliances you could need for a relaxing quiet stay. Large and spatial, including an outdoor patio area. Includes private parking, security features and a quiet space within walking distance of Bromley, or direct trains into 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 Lullingstone
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 Greater London
4.91 out of 5 average rating, 208 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
Home in Green Street Green
5 out of 5 average rating, 8 reviews

Sleeps 7 | 3BR Modern Cottage w/Netflix

Welcome to THE CORNERSTONE COTTAGE, part of the curated DUKE STAYS collection of modern, boutique homes. Newly styled with cosy yet luxe interiors, 3-BDR retreat in Orpington sleeps up to 7. Less than a mile from High Street shops, cafés & parks, with fast links to London & the M25. Styled for comfort with luxe linens, fully equipped kitchen, cosy lounge with sofa bed, 55” HDTV + Netflix, high-speed WiFi & self check-in. Ask about corporate, family, long-stay & last-minute bookings

Guest favourite
The spacious living area features a large sectional sofa adorned with decorative pillows, a coffee table with magazines, and a flat-screen television. Natural light enters through skylights above, highlighting vibrant artwork on the walls and a lush green plant in the corner.
Earthen home in Greenwich
4.93 out of 5 average rating, 715 reviews

Huge Luxury Studio Use of Parking & Garden

This unique space is huge, 500 sq ft!! and is close to Greenwich, Blackheath, The 02, Canary Wharf, City Airport and with a quick train journey to central London. You'll love the studio because of the location, the amazing views of canary wharf and the 02, with garden and key-box entry. This huge space is about the size of 4 London hotel rooms and so is a bargain. My place is good for couples, solo adventurers and families with young kids. Please read our 900 plus reviews.

Top Guest favourite
Guest suite in Brasted
4.95 out of 5 average rating, 107 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
A charming cottage is set against a clear blue sky, featuring a pitched roof and two gabled dormer windows. Flowering plants and green grass frame the inviting entrance, highlighting the cottage's warm yellow door and brick exterior.
Cottage in Kent
4.96 out of 5 average rating, 214 reviews

Cosy Private Cottage in Wrotham, Kent Downs AONB

Set on the edge of Wrotham village in the Kent Downs Area of Outstanding Natural Beauty. This self contained one bedroom cottage comes with free off street parking and use of a large cottage garden. We welcome well behaved dogs. A two minute walk into Wrotham Village, with a picturesque church, village shop, and three pubs including the AA Rosette awarded Bull Hotel. Now with a newly completed private patio to the rear solely for guest use. Dog secure with high gate.

Guest favourite
An open living space is showcased, featuring modern furnishings and large windows allowing natural light. A spacious green sofa is positioned near a wooden coffee table, and a tropical-themed rug adds warmth. The kitchen area is equipped with sleek cabinets and appliances, visible in the background.
Apartment in Greater London
5 out of 5 average rating, 23 reviews

Palm Tree House - The Forest

Welcome to our Brand New, Stylish-themed studio in a building with Lift. Enjoy modern furnishings, a fully equipped kitchen with a washing machine and dishwasher, a spacious bathroom with shower, a cosy bedroom area, and a private balcony. Free access to the shared GYM and WORKSPACE. Take advantage of free parking, super-fast WiFi throughout, and a smart TV. It is just minutes from Orpington station, with easy access to London. POTENTIAL FOR NOISE, READ BELOW.

Top Guest favourite
Tiny home in Abbey Wood
4.99 out of 5 average rating, 107 reviews

Modern Self-contained Studio near Elizabeth Line

Welcome to our peaceful London studio designed for comfort, privacy, and well-being. With independent access and thoughtful amenities, it’s an easy place to settle in and unwind after exploring the city. - Sleeps 1 | 1 bedroom | 1 bed | 1 bath - Rainfall walking shower & heated towel rail - Central heating & portable fans - Kitchen & bathroom essentials - Washer & free dryer - Free street parking & luggage drop-off

Top 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, 203 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 Orpington holiday rentals

When is the best time to visit Orpington?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Orpington?

    Orpington has more than 80 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Orpington?

    Experience the best of Orpington with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Orpington?

    Four-legged friends are welcome in Orpington. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Orpington?

    Yes! Work meets play with ease at over 110 vacation rentals in Orpington featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Orpington?

    Make yourself at home in Orpington by choosing from our most frequently booked neighborhoods. We have over 750 vacation rentals in Orpington, over 4,230 vacation rentals in Chislehurst, and over 470 vacation rentals in Bickley.

  • Do house rentals in Orpington have a kitchen?

    Absolutely! We offer over 110 house rentals with a kitchen in Orpington. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Orpington have wifi?

    Absolutely! We offer over 60 apartment rentals with wifi in Orpington. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Orpington have free parking?

    Absolutely! We offer over 100 house rentals with free parking in Orpington. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Orpington

  • Total holiday rentals

    Explore 240 holiday rentals in Orpington

  • Nightly prices starting at

    Orpington holiday rentals start at $28 AUD per night before taxes and fees

  • Verified guest reviews

    Over 3,140 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    230 of Orpington holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Orpington rentals

  • 4.6 Average rating

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

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