Start with the numbers, not the photographs

It is easy to fall for a cottage because of the flagged kitchen floor and the view across the valley. Before you do, work out exactly who is coming and what they actually need. A family gathering in the Yorkshire Dales usually means a mix of ages: grandparents who want a ground-floor bedroom, a couple of teenagers who would rather not share with a seven-year-old, and someone who has volunteered to cook for twelve. Write the list down, names against beds, and count it twice.

Then check the difference between sleeps and bedrooms. A property advertised as sleeping ten may do so with two doubles, a twin and a sofa bed in the lounge — perfectly pleasant for a weekend, less so when the sofa bed is in the room where everyone wants to sit after a day on Ingleborough. Ask how many proper beds there are, how many are bunk beds, and whether any of the sleeping space is in an annexe or converted barn away from the main house. For a big group, that separation can be a bonus; for a family with small children, it can be a nuisance.

Sleeping arrangements that keep the peace

Think about how the group naturally divides. The most successful large cottages tend to have bedrooms spread over two or three floors, with at least one bathroom per four or five people, and a mix of doubles and twins so that couples and singles can be shuffled about without anyone feeling hard done by.

• Ground-floor bedroom and bathroom — essential if anyone has mobility issues, and useful for a grandparent who would rather not tackle a steep Dales staircase at two in the morning.
• En-suite rooms — worth paying a little more for when two or three family units are sharing. It removes the morning queue and the politics of who gets the bathroom first.
• Bathrooms, not just showers — after a wet walk up Buckden Pike, a deep bath earns its keep. Check whether there is a decent shower as well, and whether the hot water is on a timer that will run out halfway through the fifth person.
• Dog-friendly rooms — if a Labrador is coming, ask whether dogs are allowed upstairs and whether there is a boot room or utility where a wet dog can dry off.

Dining and sitting space for everyone at once

This is where large holiday cottages most often disappoint. A dining table that seats eight in a house that sleeps twelve means somebody is eating off their knee. Ask for the seating numbers for the table and for the sitting room, and be specific — a photograph showing a long oak table with twelve chairs is worth more than any description.

Look for an open-plan kitchen and dining area if you plan to cook together, or a separate dining room if you would rather keep the noise of a big meal away from anyone reading by the fire. Two sitting rooms are a genuine luxury for a mixed-age group: the children can watch a film in one while the adults talk in the other. Games rooms, snugs with wood burners, and a decent-sized garden with a terrace all add to the sense that nobody is tripping over anybody else.

Kitchens, parking and the unglamorous details

A catering-sized kitchen is rarely what you get in a Dales cottage, so check the practicalities before you commit to cooking Christmas dinner for fourteen. Two ovens, a large fridge, a separate freezer, a dishwasher and enough pans and roasting tins make far more difference than granite worktops.

• Parking — count the spaces. Many cottages in villages such as Reeth, Kettlewell or Hawes have room for two cars and a narrow lane outside. If four households are arriving, ask where the rest will park.
• Heating and hot water — oil-fired ranges and wood burners are charming, but ask whether there is central heating too, and whether logs are included.
• Wi-Fi and mobile signal — patchy at best in the upper dales. If someone needs to work, or a teenager needs to stream, confirm what the connection actually supports.
• Arrival times and keys — large properties can take longer to clean between guests, so late-afternoon check-ins are common. Plan the supermarket run accordingly.

Location: what is genuinely on the doorstep

The Dales rewards a bit of thinking about driving. A cottage near Skipton, Leyburn or Settle puts you within easy reach of shops and pubs, while a remote farmhouse above Swaledale offers silence and stars but a twenty-minute single-track drive to the nearest pint. Neither is better; they simply suit different gatherings.

Consider what the group will want to do. Walkers will want paths from the door — the Three Peaks, Malham Cove, Aysgarth Falls and the waterfalls at Ingleton all draw crowds at peak times, so a base slightly off the main honeypots can mean quieter mornings. Families often appreciate a garden with a bit of flat grass, a stream nearby, and a pub within walking distance that serves food in the early evening. Check opening times out of season, when several village pubs reduce their hours.

Booking sensibly and reading the small print

Large properties go early for school holidays, half-terms and the weeks around Christmas and New Year, often a year ahead. For a gathering of several households, book as soon as the dates are agreed and take a moment over the terms.

• Confirm the deposit and balance dates, and the cancellation policy — group bookings often carry stricter conditions.
• Ask about any additional charges for extra guests, dogs, logs or electricity, particularly in older properties with electric heating.
• Check whether the price is based on occupancy. Some owners charge per person above a certain number.
• Speak to the owner or agency directly if anything is unclear. A short conversation about beds, parking and access will tell you more than any listing.

Get those details right and the rest takes care of itself: long walks, a big table, a fire lit at dusk, and three generations happily under one Dales roof.