Begin with the road, not the view

It is easy to fall for a photograph of a stone cottage under a purple sunset, but the practical question comes first: how far are you willing to drive for a pint of milk? In the Highlands, "remote" can mean anything from a ten-minute hop into a Highland town to a forty-minute single-track road with passing places and a resident deer population. Work out your daily radius before you book. If you plan to walk in Glen Affric, eat out in Inverness, and catch a ferry from Ullapool, a cottage near Aviemore might look central on a map but will leave you facing two hours of driving before breakfast.

Think about the roads you will actually use. The A9, A82, and A835 are reliable year-round, though winter closures happen. Side roads toward Torridon, Applecross, or the quieter glens are glorious and slow. A cottage five miles up a track is a delight in June and a serious proposition in January, especially if you arrive after dark.

Heating is the whole ball game

Highland weather does not negotiate. Even in July, an evening can drop to single figures, and a wet walk needs somewhere warm to come back to. When you read a listing, look past the word "cosy" and find out exactly what heats the place.

• Wood-burning stove: lovely, but ask whether logs are included and whether the stove is the main heat source. If it is, you will be chopping kindling on your holiday.
• Oil-fired central heating: the Highland standard, usually reliable and quick to warm a cold stone wall.
• Electric storage heaters or panel heaters: fine in a well-insulated modern build, grim in an old croft house with single glazing.
• Heat pumps and underfloor heating: increasingly common in new conversions, but they warm slowly, so ask for the heating to be switched on before you arrive.

Ask directly: is the heating included in the price, or metered separately? Some owners charge for electricity used, which is fair in a draughty cottage but can add a surprising amount to a winter week. Also check for a drying room, a boot rack, and somewhere to hang soaking waterproofs. In a wet climate, a proper drying space matters more than a fancy bathroom.

Check the boring details that make a stay work

Broadband and mobile signal are patchy across the region, and "superfast" claims deserve scrutiny. If you need to work, ask for a speed test screenshot rather than a promise. If you do not, a digital detox is a genuine pleasure, provided you know the score in advance and download your maps and music before you leave the last decent signal.

Other questions worth asking before you commit:

• Is the water from a private supply? If so, is it filtered and is the pressure decent for showers?
• Is there off-road parking for the number of cars in your group?
• Does the kitchen have a full-size oven, a decent knife, and a cafetière? Self-catering kitchens vary wildly.
• Is there a freezer big enough for ice packs and a catch of mackerel?
• Are pets genuinely welcome, or merely tolerated, and is the garden secure?

Match the cottage to the season

The Highlands give you four very different holidays from the same address. Summer brings long light, midges in still, damp air, and busy car parks at the classic viewpoints. Spring and autumn offer quieter roads, golden birch woods, and the best conditions for hillwalking. Winter is for low-level walks, fireside afternoons, and the chance of snow on the tops, though you should carry a shovel, check road conditions, and be flexible.

Midges deserve a mention because they shape evenings outdoors. A cottage with a sheltered seating area, a porch, or a conservatory gives you somewhere to sit when the wee beasties are out. Smidge and midge nets help; a breezy spot helps more. If you are travelling in July or August, ask whether the windows have insect screens.

Think about the last mile and the first morning

The final stretch of any journey shapes your first impression. Find out where the nearest shop is and what time it shuts. Inverness, Dingwall, Fort William, and Thurso have supermarkets with long hours, but many villages rely on a community shop that closes at five and shuts on Sundays. Arriving with the basics already in the boot, milk, bread, butter, coffee, a bottle of something, turns a stressful evening into a relaxed one.

It is also worth checking what is within walking distance. A cottage on the edge of a village with a pub, a café, and a footpath from the door gives you the option to leave the car parked, which is one of the quiet luxuries of a Highland holiday.

Read the reviews for weather, not just décor

Reviews written in winter tell you more than glossy summer photographs. Look for comments about warmth, water pressure, road access, and how the owner handled a problem. A thoughtful owner who leaves torches, a well-stocked log basket, and clear directions for the last half mile is worth more than granite worktops. Book directly where you can, ask your questions plainly, and confirm the cancellation terms, because Highland weather sometimes rewrites the best-laid plans. Choose well, and the cottage becomes part of the holiday rather than just a base for it.