Multi-generational family walking on a beach
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How to plan a multi-generational holiday - The ultimate guide

14th February 2025

The rise of multi-generational travel is a wonderful new trend in the UK that’s reshaping how families spend time together. British families are embracing the multi-generational break, that sees grandparents going away with their children, and grandchildren - all on one amazing trip together. Picture grandparents sharing stories, children playing, whilst parents enjoy some peace and time with their nearest and dearest.


The magic of a multi-generational stay lies in its ability to unite different age groups through shared experiences. With busy schedules and distance often keeping loved ones apart, these holidays provide a valuable chance to reconnect in a special location, be it amidst rolling hills, craggy coastlines, or ancient woods.

Here at Coolstays we offer an array of properties that cater perfectly to multi-generational stays. So in today’s guide, we’re outlining for you some of the steps you may wish to take when planning your next getaway with the whole family.

Large family? Find out everyone’s specific requirements

Before you start looking for the perfect property for your multi-generational break, you’ll want to make sure you are aware of everyone’s specific requirements. There may be some non-negotiables that may influence your search, so it’s always a good idea to be aware of these from the offset.

Some things that you’ll want to ask people about include:

How are they going to be travelling to the property?


It’s important to understand where everyone is travelling from and how they are going to be getting to and from the property. Your older friends or relatives, for example, may not want to drive too far, meaning you’ll need to opt for a location closer to where they’re living. Or perhaps some members of your group will be making use of public transport, so a good train or bus connection might be vital. Then there’s anyone travelling with children. These individuals may not fancy a long drive with two cooped up toddlers in the car.

So get an idea of people’s willingness to travel, and it will help you narrow down your destination list when planning your trip.

Does anyone have any specific accessibility requirements?


If you’re planning a trip for different generations, you will want to be aware of any specific accessibility requirements that members of your group may have. If you’re travelling with older people, are they comfortable walking through uneven terrain to access the dwelling? If not, this may rule out some more rural or off-the-beaten-track stays.

Some people may also prefer to avoid climbing up stairs, which again can rule out specific stays. Or, you may be able to find a stay with a number of bedrooms on the ground floor to accommodate these specific needs.

What age are the children you’re travelling with?


The odds are, if you’re organising a multi-generational holiday, there will be some children travelling with you. If this is the case then consider their ages. If they are infants, then you’ll need to know ahead of time if the property can provide cots (so parents know to bring their own if not). If the children are slightly older, then you’ll want to ensure there are suitable bedrooms for them to make use of.

Also, in order for children to remain entertained during your stay, you’ll want to consider the facilities at the property. Younger children may love a playpark in the garden with swings and a slide. Slightly older children could make use of a games room with a pool table or table football. Just make sure that when you’re planning, you take into consideration the needs of everyone involved.

Try and be as flexible as possible


Despite talking above about the non-negotiables, it is very important that people try to be as flexible as possible. This is because an unwillingness to compromise may lead to you being unable to find a place to stay. It may be impossible to find somewhere in the right location that ticks every box.

So we advise you to pick your battles wisely. If one person claims that one specific aspect of the stay is absolutely vital for them, but everyone else isn’t that bothered, then it’s probably best to go with it. Set your parameters, understand everyone’s wants and needs, and try to find a stay that ticks as many boxes as possible.
Multi-generational family walk

Choosing the right activities for a multi-generational break

Finding the right property in the right location is one thing, but planning activities for you to enjoy during your break is another one entirely. But, for some groups, the activities are just as important as the accommodation. And when travelling with people of all ages, there’s a lot to consider.

Remember, you don’t have to spend all of your time together


It’s important to remember that you do not always have to spend all of your time together. If you’re going away for a week, then the odd afternoon, or even full day apart is fine. If you’re relaxed about this, it means that if people have certain things that they would like to do, they can still do it, without feeling like they’re breaking up the group.

This can be great for anyone looking to go on a bracing hike that might be too strenuous for the older members of your party. Similarly, your older relatives may have their eye on a particular cultural excursion that children might not be interested in - a visit to a specific museum for example.

If you’re flexible with your time, and allow for the odd moments where the group’s split up, it’ll be all the more special when you do spend quality time together back at the property.

Days out as a group


Some days out are simply not suitable for everyone. Kids might not have the most fun hopping from pub to pub in a charming market town. And older travellers may struggle spending the day on their feet exploring museums, galleries, and other historic destinations. There are, however, certain locations that may work nicely for multi-generational groups.

For example, the beach can be suitable for all ages. Grandparents might enjoy sitting in a seaside pub or lounging on a deck chair with a good book whilst kids play in the sand. Parents and kids can also spend time swimming in the sea whilst older relatives paddle and feel the water on their skin.

Other great days out that might suit your group include days at the park picnicking and playing on the grass, boat rides across lakes or down winding rivers, or trips on steam trains that take you through gorgeous rolling countryside.

Activities at the property


Whilst big fun days out can be a great way to spend time together as a group, you may also want to look into activities you can do on-site, wherever you’re staying. If board games are your thing, then you may want to find a property with a suitable area to play, and maybe even one that provides the games for you. If you know that some of your group love a game of tennis, then you could even look for accommodation that has its own tennis courts.

Kids and parents alike will often love a swimming pool, which can really make your stay special - just be sure not to leave little ones unattended in the water.
Stillwaters at Avington Estate
Stillwaters at Avington Estate, sleeps 14

Choosing the right property for a multi-generational holiday

Here at Coolstays we’re the experts when it comes to staycation destinations. So why not take a look at some of the accommodation options that we have available to help you plan your next multi-generational break?

Cottage or barn for a rural retreat for families


If you’re looking for a stay that offers a number of areas to socialise together as a group, whilst still providing you with nooks and crannies where you can head for some relaxation, then a charming old cottage or a converted barn might just be for you. These properties often offer delightful living rooms with open fires and lots of comfy seating for you to gather together as a group. And, they are also great for providing cosy snugs where older relatives can retire with a book for a bit of peace.

Beach house for a stay by the sea for a group stay


We’ve already established that the seaside is a lovely spot for a multi-generational getaway. People of all ages love days at the beach. And here at Coolstays, we’ve got a vast array of amazing seaside homes that offer great access to the beach and modern, spacious interiors that are ideal for big multi-generational groups.

Modern home for a luxury break


Whilst a converted barn or beautiful old cottage offer up cosy nooks and rustic charm, spacious contemporary homes are at the other end of the spectrum offering big groups, giant open-plan living areas and modern luxuries. These contemporary retreats often offer up desirable features like hot tubs, free-standing baths, underfloor heating, swimming pools, and more. Add to this their clean, minimalist design and you’ve got the perfect place to unwind together with loved ones. Kids will often love the hot tub or swimming pool, whilst luxury features like underfloor heating, heated towel rails, and ensuite bathrooms will often appeal to older loved ones.

Boutique hotels for larger groups


One type of stay that we’ve not really touched on in this blog post, is the option of booking a number of rooms in a nice hotel. Whilst this definitely has some drawbacks - such as the lack of communal living spaces in which to socialise together - it does offer plenty of privacy and allows older relatives to head off to their own room at night, offering peace and quiet. A hotel is mostly a good option for groups that intend to spend days out and about, on excursions, offering a comfy base to retire back to at the end of the day.
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