Holiday houses in Orpington

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Quick stats about holiday rentals in Orpington

  • Total holiday rentals

    Explore 250 holiday rentals in Orpington

  • Nightly prices starting at

    Orpington holiday rentals start at $53 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,180 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wi-Fi availability

    240 of Orpington holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Orpington rentals

  • 4.7 Average rating

    Orpington stays receive an average rating of 4.7 out of 5 from guests

Top-rated holiday rentals in Orpington

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Guest suite in Chislehurst
5 out of 5 average rating, 31 reviews

Large studio with free parking, Chislehurst London

Stylish Spacious Studio | Private Entrance | Free Parking Relax in this peaceful, modern studio in Chislehurst, London, on a quiet private road with your own entrance and free parking. 5 min walk to Elmstead Woods station - 20 min train to London Bridge - 30 min train to Central London The charming Chislehurst village high street is 5 min drive away, with its boutique shops, restaurants, pubs and cafés. The historic Chislehurst Caves and scenic National Trust walking routes are 1 mile away.

Top Guest favourite
Home in Greater London
5 out of 5 average rating, 19 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 charming exterior showcases a well-maintained building with a tiled roof and large glass doors. A basketball hoop stands beside the entrance, surrounded by lush greenery. A gravel driveway leads to the building, providing ample space for parking and outdoor activities.
Guesthouse in Warlingham
5 out of 5 average rating, 58 reviews

Where Country meets Suburbs

Situated in the picturesque countryside of Warlingham, there is something for everyone; a variety of pastimes that will appeal to that naturistic inner being and or a well-deserved relaxing break. Close to Biggin Hill Airport and London Gatwick Airport. Easy access to London. Central to four Golf Clubs in the area. Various dinning options, including the famous White Bear Gastro Pub (2 min walk). See the history of Charles Darwin and visit his house. Walking and cycling trails, and Much More!

Top Guest favourite
A freestanding bathtub filled with water and flower petals is complemented by a wooden tray holding a glass of wine and an open book. A large ornate mirror and wall-mounted lights enhance the serene atmosphere. A hand towel and bath robe hang nearby.
Place to stay in Box Hill
4.97 out of 5 average rating, 176 reviews

Potting Shed, freestanding bath

Welcome to The Potting Shed Surrey Hills it’s ian exquisite retreat, offering a perfect blend of luxury and tranquility. Watching the sunrise while soaking in your freestanding bath amidst 6 acres of private land is truly magical. It’s luxurious and stylish decor creates an unforgettable experience for guests seeking relaxation and indulgence. From AONB country walks to the personalised room service, the Potting Shed offers a level of extravagance that sets it apart from other retreats.

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.
Apartment in Orpington
4.91 out of 5 average rating, 214 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 Orpington
4.83 out of 5 average rating, 18 reviews

4 Bed House + Loft Space, Petts Wood, Orpington

4 bedroom new modern house ⭐ ⭐️ Contractors and long stays welcome please contact for bookings ⭐️ 📅 Long-Term Discounts Available - Enquire Now for the Best Rates! 🏠 ✅ 4 Spacious double Bedrooms - Comfortable beds for a great night's sleep. ✅ 1 Modern Bathrooms - Perfect for larger groups . ✅ Bright & Cozy Living Area - Relax with a Smart TV & high-speed Wi-Fi. ✅ Superfast Free Wi-Fi - Stay connected for work & entertainment. ✅ 3 car spaces on drive and free parking on road .

Guest favourite
Home in Green Street Green
4.94 out of 5 average rating, 16 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 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 Bromley
5 out of 5 average rating, 17 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.

Superhost
Apartment in Orpington
5 out of 5 average rating, 6 reviews

Palm Tree House Columbus

Experience comfort and style in this chic 40 sqm flat in Orpington, featuring a private terrace and lift access. This modern space offers a cosy bedroom area, a spacious bathroom with a shower, and a fully equipped kitchen with a washing machine and dishwasher. Guests enjoy free access to a shared gym and workspace, plus superfast WiFi, Smart TV, and free parking. Conveniently located just minutes from Orpington Station with easy access to London. Potential for noise. Read below.

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
5 out of 5 average rating, 67 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.

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 Chessington
4.98 out of 5 average rating, 360 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, 104 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 Orpington holiday rentals

When is the best time to visit Orpington?

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Avg. price$238 NZD$243 NZD$234 NZD$208 NZD$211 NZD$217 NZD$222 NZD$226 NZD$236 NZD$234 NZD$231 NZD$248 NZD
Avg. temp5°C5°C7°C9°C12°C15°C17°C17°C15°C11°C8°C5°C

Frequently Asked Questions

  • What are the best places to stay in Orpington?

    Stay in the town centre for easy access to shops and dining, or choose a vacation rental in residential areas near parks for a quieter atmosphere. Many neighborhoods have homes suitable for longer stays and families.

  • What are the best things to do in Orpington with kids?

    Families often explore playgrounds in parks like Priory Gardens, visit animal encounters at High Elms Country Park, or join workshops in local museums. The area has indoor activity centres and family-friendly dining options.

  • What are some of the best things to do in Orpington?

    Wander historic sites like Orpington Priory, stroll leafy parks, and enjoy shopping or markets in the town centre. The area has museums, community arts, and venues hosting local performances.

  • How is the weather in Orpington?

    Orpington has cool, wet winters around 36–46°F (2–8°C), with milder springs and summers reaching 55–71°F (13–22°C). Rain is frequent year-round, so waterproof gear is helpful for outdoor plans.

  • When is the best time to visit Orpington?

    Late spring through early autumn is often recommended for milder temperatures near 55–71°F (13–22°C), longer daylight, and outdoor activities. Winter brings cooler weather around 36–46°F (2–8°C) and frequent rain.

  • What are the best places to visit in Orpington?

    Orpington has historic sites like the Orpington Priory, welcoming parks such as High Elms Country Park, and a town centre filled with shops, markets, and community spaces. Green areas around the town are frequently suggested for outdoor walks and picnics.

  • What are some hiking trails in Orpington?

    Explore footpaths through local parks such as the Priory Gardens, or follow routes in High Elms Country Park, which has woodland trails and open meadow walks. The area is also known for access to green spaces around the town.

  • What are some family activities we can do in Orpington?

    Families can enjoy parks with playgrounds, join creative workshops at local museums, or visit animal habitats at High Elms Country Park. Indoor play centres and community arts venues are also frequently suggested.

  • What are some of the best day trip ideas from Orpington?

    Explore historic towns, gardens, and countryside spots just outside Orpington, or visit local heritage sites and nature reserves nearby. Larger cities in the region have museums, galleries, and diverse dining options.

  • Are there any pet friendly accommodations available in Orpington?

    Orpington has a selection of pet friendly accommodations, including vacation rentals and homes. Many hosts in residential neighborhoods welcome pets, so you can bring a furry friend along for your stay.

  • What are some local tips for visiting Orpington?

    Locals recommend exploring weekend markets early, using park paths for peaceful walks, and checking community notice boards for events. Carrying a raincoat and reusable shopping bag helps with changing weather and local shopping.

  • What is Orpington known for?

    Orpington has a mix of historic gardens, community markets, and green spaces. The area is often recognized for its Priory, local heritage stories, and easy access to countryside activities.

  • What are the best hidden gems to explore in Orpington?

    Consider creative spots like local art studios, gardens tucked behind historic buildings, or smaller museums with neighborhood stories. Quiet woodland trails in High Elms Country Park invite peaceful walks.

  • What are the best foods to try in Orpington?

    Orpington has hearty British classics, locally baked goods, and seasonal produce from community markets. International cuisines can be sampled at neighborhood restaurants for diverse palettes.

  • What should I bring for a trip to Orpington?

    Pack a waterproof jacket, comfortable walking shoes, and an umbrella due to frequent rains, especially in cooler months. Layers help with changing temperatures, and a reusable bag suits visits to local shops or markets.

  • What is the nightlife in Orpington like?

    Orpington has relaxed pubs, casual bars, and places for evening dining around the town centre. Live music, quiz nights, and community events are frequently suggested for a local night out.

  • What are the most popular events or festivals in Orpington?

    Recurring community fairs, local food markets, and seasonal festivals such as summer fetes and holiday light displays are often recommended. Performances and arts events also highlight the area’s calendar.

  • Are there family friendly vacation rentals in Orpington?

    Orpington has a variety of family friendly vacation rentals, many with gardens and spacious living areas. Neighborhoods around local schools and parks frequently host welcoming stays for families.

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