Vacation rentals in Orpington

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Quick stats about vacation rentals in Orpington

  • Total vacation rentals

    Explore 260 vacation rentals in Orpington

  • Nightly prices starting at

    Orpington vacation rentals start at G$6,275 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,400 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

    130 properties have a dedicated workspace

  • Wi-Fi availability

    250 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
Condo in Eltham
4.93 out of 5 average rating, 369 reviews

Free Parking | Private Flat Near O2 & Greenwich

Private self-contained flat with free parking in peaceful Avery Hill, South East London. Ideal for couples, families, business travellers and O2 visitors. Features a private entrance, king-size bed, single bed, sofa bed, shower room, living area, kitchenette, WiFi and courtyard seating. Close to Greenwich, Blackheath, Eltham Palace and The O2, with excellent links to Central London. ✓ Sleeps 4 ✓ Free parking ✓ Self check-in ✓ Private entrance ✓ Fast WiFi ✓Courtyard ✓ Near 02 Arena & Greenwich

Guest favorite
Home in Eltham
4.95 out of 5 average rating, 22 reviews

Lovely 3 double bed large house, fully renovated

Bring the whole family to this great place with lots of room for fun. Two reception rooms, downstairs washroom, large modern bathroom, fully fitted kitchen, large garden and parking in own gated driveway. Close to two overland train stations 15 mins walk away. Close to bus stops, shops and restaurants. Opposite to a park. Places of interest, Eltham Palace, Greenwich park with the Royal Obsevatory, Royal naval college, cutty Sark Clipper, Leeds Castle, Hever Castle, Hall Place, Penshurst Manor.

Guest favorite
Home in Greater London
4.96 out of 5 average rating, 24 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.

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, 217 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 favorite
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
4.91 out of 5 average rating, 116 reviews

Gingerbread House in a quiet woodland setting

Gingerbread House, popular with families, 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, sightseeing in Kent/Sussex, or events at Brands Hatch. The village of Pratts Bottom and the local pub is within a 8 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 favorite
Guest suite in Chislehurst
4.92 out of 5 average rating, 114 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 favorite
An open-plan living and dining area is visible, featuring a circular dining table surrounded by green chairs. A modern kitchen with white cabinets is in the background. Natural light fills the space through large glass doors that lead to the patio.
Guest suite in Greater London
4.98 out of 5 average rating, 50 reviews

2 bed detached home in Bromley

Welcome to your beautiful 2 bedroom home in Bromley, BR2!. The property has been recently refurbished to a high standard, featuring an open plan living and dining area, modern kitchen and triple glazed windows. It is perfect for families or couples and there is off street private secure parking. Located in a quiet area close to shops, restaurants, and transport links, our home is the perfect choice for your London getaway. Book now and enjoy a comfortable and convenient stay!

Top guest favorite
Guest suite in Chislehurst
5.0 out of 5 average rating, 13 reviews

1BR Chislehurst | Free Parking | 20minTrain to Ldn

Stylish Fully Equipped One-bedroom Apartment | Free Parking Relax in this peaceful, modern one bedroom apartment in Chislehurst, London, on a quiet private road with 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 and eateries. The historic Chislehurst Caves and scenic National Trust walking routes are 1 mile away.

Top guest favorite
A private outdoor space is showcased, featuring a well-maintained lawn, wooden fencing, and a small dining set with four chairs underneath a dark umbrella. The sliding glass doors of the guest house provide access to the interior.
Guesthouse in Greater London
4.97 out of 5 average rating, 73 reviews

Guest House 1 double bed

Take it easy at this unique and tranquil getaway close to Bromley town centre. Complete with its own entrance this stylish guest house has everything you need for your stay. A double bed, dining table & chairs, oven, hob, microwave, kettle, fridge and washing machine. The bathroom includes an electric shower and there's strong wifi and a wall mounted tv with free access to Netflix, Sky, Amazon and Apple TV+. Bed linen, towels, crockery & cutlery are of course provided.

Superhost
The exterior of a charming red-brick house is shown, featuring multiple peaked roofs and large windows. Surrounding greenery provides a natural buffer, and a street sign is partially visible in the foreground. A clear blue sky complements the architectural details of the building.
Apartment in Greater London
4.86 out of 5 average rating, 29 reviews

Apartment Masons Hill

Newley Refurbished 2 Bed Apartment in Bromley Welcome to our bright and spacious 2-bed apartment, located Close to central Bromley. The home features a large lounge & dining area, a fully equipped but small kitchen, private off street parking Just a 5-minute walk from Bromley South Rail Station, with excellent bus connections, only 17 minutes from Victoria Station, Central London. The apartment is walking distance of parks, shops, sports grounds, Gym & golf driving range

Guest favorite
A sleek kitchen area features modern cabinetry with a glossy finish and countertop space. Stainless steel appliances, including a microwave and oven, are visible. A small dining table with two black chairs is placed against the wall, accompanied by a vase of flowers.
Apartment in Kent
4.94 out of 5 average rating, 101 reviews

ENTIRE BEAUTIFUL 2 BEDROOM APARTMENT DARTFORD KENT

Enjoy a luxury experience at a peaceful centrally-located serviced apartment. Which is just 2 minute walk from dartford train station and local town centre, with food and high street shops all in walking distance for your convenience. We also have parking for your car. Also you can enjoy free WiFi with smart Tvs in the living room and bedroom. As well as an en-suite off the master bedroom and a main bathroom that makes you feel at home.

Superhost
Apartment in Chislehurst
5.0 out of 5 average rating, 3 reviews

1BR Flat | Sleeps 3 | High Street

❗New listing 20% discount offered ❗ Stylish 1-bedroom flat in the heart of Chislehurst High Street, surrounded by restaurants, cafés and shops. Ideal for couples, solo travellers and business guests, with central London around 30–40 minutes away. The flat includes a comfortable bedroom, Smart TV , fully equipped kitchen , bathroom with bath and shower, and a dedicated workspace —perfect for short stays or longer visits.

Popular amenities for Orpington vacation rentals

When is the best time to visit Orpington?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$28,238 GYDG$28,865 GYDG$27,819 GYDG$30,538 GYDG$32,421 GYDG$32,212 GYDG$26,355 GYDG$26,773 GYDG$28,028 GYDG$27,819 GYDG$27,401 GYDG$29,493 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.