The Dos (and Don’ts!) of Planning a Large Group Holiday

27 March 2024

With everyday life always so rushed and hectic, there’s nothing like downing tools and taking a well-deserved holiday with your favourite people – all at the same time.

But if all that potential organising makes you break out in a cold sweat, don’t worry.

We won’t just take you through the planning process step by step. We’ll also point you in the direction of some of the most unusual, wow-factor holiday homes around… for a little extra kudos!

What are the benefits of booking a large group holiday?

Whether you’re planning a specific celebration or a ‘just because’ getaway, it feels incredibly special – even luxurious – to go on holiday as part of a cosy group.

Let’s face it: in the constant whirlwind of busy schedules and the demands of everyday life, how often do you get to see everyone you love, all together?

So your group holiday is a precious time to make lasting memories, through relaxed catch-ups and fun-filled experiences… the sort of things that inspire excited, laughter-fuelled: “do you remember when…” chats years later!

While you could easily book a standard hotel for your large group holiday, wouldn’t it be great if you had an entire retreat all to yourselves?

And what if that retreat was jaw-droppingly unique into the bargain?

Above: St Curigs Church, Snowdonia

OK, let’s start with a little ‘large group holiday’ inspiration.

When you book a large group holiday, you’ll find many places offer exclusive entire-site hire – often with additional ‘extras’ available, like catering or on-site activities.

This is fantastic for holiday freedom and flexibility. Everyone will get the chance to do their own thing if they want to, yet there’ll be plenty of sociable space to come together… like an enormous kitchen, or a beautiful garden that’s ideal for cocktail receptions!

Our Host Unusual categories include some truly magnificent settings for group breaks, from the cheerfully quirky to the blissfully opulent.

For starters, how about sunning yourselves on a private island, or booking out an idyllic country pub – with a fully-functional bar – all to yourselves?

Above: The Boars Head Pub, Shropshire

Step One: Choosing the right location for your large group break

If you’re the one doing the organising, it’ll be tempting to choose a place that you know you’re going to love, then presenting it to everyone else as a done deal.

However, by running a few different options past the whole group first (say: glamping, seaside stays, or a ‘Downton Abbey’-esque palatial setting) you’ll get an idea of different preferences and what the majority are likely to enjoy the most… putting you in everybody’s good books.

Be aware that some people might want some extra privacy or extra facilities, especially if they’re travelling as a family. If so, you could look around for cosy ‘reading nooks’, quiet garden spaces, dedicated children’s play areas, or even rooms with separate self-contained facilities.

Oh, and don’t forget to check the full amenities of each potential choice. If there’s a hot tub – or even a swimming pool – in the garden, or games and a cinema room inside for example, it could win a few extra points!

Above: Halula Beach House, Cornwall

Step Two: Setting a budget for your large group holiday

Although large group holidays can seem expensive when you look at the total price, bear in mind that the more people on the list, the lower the cost per person.

You could potentially save money with a self-catering break, too – just ask everyone to bring along one or two things to pool once you’re there, or nominate someone to book an online shop.

Alternatively, splash out on a private chef and put your feet up – ideal if you’re celebrating something truly special!

The key is to make sure all costs are clear from the outset (don’t forget transportation and any extra activities) and not leaving it right up to the last minute to request payment.

People will thank you for giving them as much time as possible to prepare and save up, so book your chosen retreat as far in advance as you can. You could set up a simple spreadsheet to keep track of who’s paid what in the meantime.

For the truly unusual, like themed retreats and unique conversions, you’ll need to get in extra-early anyway!

Above: Wonderland House, Brighton

Step Three: Planning an itinerary for your large group holiday

Now that you’ve decided where you’re going, it’s time for the fun part: planning your group holiday activities.

Check the property website, or speak to the owner or manager directly to see exactly what’s possible during your stay. Depending on where you’ve chosen, activities could include:

• Cookery or cocktail-making classes
• A communal firepit for glamping stays – marshmallows optional!
Spa and wellness services, like in-retreat massages or yoga
• Fun outdoor games and sports
Tailored workshops or local excursions
• Bespoke hen party activities, like life-drawing and makeovers

Don’t forget to book activities that the majority of people are going to enjoy, and give everyone the option of opting out if they’d rather not take part in a particular activity.

You could also ask a detail-oriented someone do some research into the local area – such as finding the location of the nearest pub!

Above: Browning Bros Teybrook Orchard, Essex

Step Four: Relaxing, making memories, and having fun on your large group break!

Once the organising is done you’ll have earned the right to sit back and relax, so make the most of it!

Whatever type of large group holiday you’ve got in mind – be it a hen party, a family reunion, or a long-overdue catch-up with close friends (and their dogs) – you’ll find the perfect setting in our Host Unusual listings.

We’ve even categorised them by type and feature, for even more wow-factor inspiration and stress-free planning.

So get browsing, and do your best to narrow down just a few favourites (though we warn you: with so much uniqueness and wonder to choose from, this might be tricky!)


Author: Nina Jervis
Main image: Woolbrook Reservoir, Devon


Recommended Accommodation for Large Groups:



Swipe left
to find out more

New to Host Unusual: Nostalgic Retreats, Luxury Airstream Glamping, and Caribbean Island Bliss!

Now that spring has finally sprung (well hello, sunshine!) it’s time to think about the important things in life… like...

Top 10 Host Unusual Retreats As Seen on TV during 2024!

Staying somewhere you’ve seen on TV can add an extra frisson of joy to a well-deserved holiday. Why? Well for...

Host Unusual Stays with Links to the Loveliest Local Produce!

What makes an unusual stay even better? For us, it’s sampling some of the area’s finest local produce – hands...

Meet the Owners: The Windmill Suffolk

Meet Natalie and Steve, owners of The Windmill Suffok - a glorious towering bolthole as seen on George Clarke's 'Amazing...

Try Something New in 2024! Unusual Retreats with Added Memory-Making Experiences

When you plan a holiday, booking an unusual place to stay is all but guaranteed to inspire happy memories. But...