Vacation rentals in Orpington

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Quick stats about vacation rentals in Orpington

  • Total vacation rentals

    Explore 250 vacation rentals in Orpington

  • Nightly prices starting at

    Orpington vacation rentals start at G$6,274 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,180 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wi-Fi availability

    240 of Orpington vacation 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 vacation rentals in Orpington

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

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Top guest favorite
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, 163 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 favorite
Guest suite in Chislehurst
5 out of 5 average rating, 34 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 favorite
An open-plan living area is highlighted by natural light from a skylight. A modern kitchen features a large marble-topped island with seating. A comfortable sofa adorned with patterned cushions faces a wall-mounted smart TV, providing a cozy space for relaxation and gathering.
Boat in Limehouse
4.97 out of 5 average rating, 110 reviews

Luxurious houseboat in London

The houseboat is a unique place to stay in London, within easy reach of all of London’s landmarks, including Tower Bridge and Tower of London (5 mins by train). The boat is moored within a marina which means that there is very limited boat movement on the water. The houseboat is custom-designed with every possible comfort, including super fast Wifi, smart TV with content streaming services, and supremely comfortable beds. Radiators throughout the boat make this a comfortable year round option.

Top guest favorite
Home in Greater London
5 out of 5 average rating, 20 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 favorite
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!

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).

Top guest favorite
Guest suite in Chislehurst
4.93 out of 5 average rating, 110 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.

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 favorite
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, 72 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 favorite
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, 362 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 favorite
Bungalow in Kent
4.97 out of 5 average rating, 105 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.

Top guest favorite
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
4.98 out of 5 average rating, 167 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.

Popular amenities for Orpington vacation rentals

When is the best time to visit Orpington?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$28,234 GYDG$28,861 GYDG$27,816 GYDG$24,678 GYDG$25,097 GYDG$25,724 GYDG$26,352 GYDG$26,770 GYDG$28,025 GYDG$27,816 GYDG$27,397 GYDG$29,489 GYD
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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