Short break or big trip? Holidays to book now

The city break

October is the perfect time to explore Lisbon without breaking into a sweat, while still enjoying mild evenings. It’s also a time when flight prices drop (Lisbon can be surprisingly expensive to fly to). Easyjet and Ryanair both have sales on this month – the former offering 15% off, the latter 20%. At the time of writing, we found flights with Ryanair from Stansted to Lisbon for less than £100 return around weekends in October and just £69 return if you fly Saturday-Wednesday. Getting a cheap bed in the city doesn’t mean compromising on style: it’s home to several award-winning hostels, such as the Travellers House, which has private doubles from just €30pp a night.

New York is another option. Come the end of November, around Thanksgiving and then leading up to Christmas, the cost of travelling to the Big Apple rockets. So get the festive shopping in early with a trip in October or early November: fly Tuesday to Tuesday with Norwegian for £240 return.

Short-break UK escapes

Peaky blinder … dry stone walls and fields in the Peak District, Derbyshire.
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 Peaky blinder … the Peak District, Derbyshire. Photograph: Christopher Thomond for the Guardian

This month, Matlock, on the edge of the Peak District, sees the start of its annual illuminations. Every Saturday from 9 September until 28 October there will be a light show at Matlock Bath, including boats festooned in coloured lights and a firework display. If you’re going for a quiet break, add to the adventure by booking a stay in a cosy shepherd’s hut: Peak Glamping still has weekendavailability in September, from £100 a night. For families, Barn Farm Camping, three miles west of Matlock, has five barns that sleep between 2 and 15, from £85 a night. For something more active, head to Anglesey for a yoga and wild swimming weekend. Run by Zest Life, prices start at £450pp.

The week (or more) away

Panoramic aerial view of Venice from San Marco Campanile.
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 Panoramic aerial view of Venice from San Marco Campanile. Photograph: smiltena/Getty Images

As with Lisbon – but even more so – Venice is a hot summer destination that offers more breathing space in autumn. Citalia is offering the chance to visit the city for three nights, followed by seven nights lazing beside Lake Garda for £1,099, including flights from London with BA, departing on 9 October. The operator is also offering a £100 discount on any holidays booked during September, which take in more than one destination, so it’s worth having a browse.

The big trip

Shinsekai, Osaka, Japan
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 Shinsekai, Osaka.
Photograph: Alamy

Those who have always dreamed of visiting Japan should take inspiration from a new set of itineraries to the country from Rickshaw Travel. It offers a range of two- to three-day “bite-size” trips that can bolted together into a big trip – or opt for its Japan in a Nutshell itinerary: a 10-day trip taking in Tokyo, Osaka and Kyoto, from £1,598pp.