The Ultimate Winter Staycation in the UK Checklist

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If you, like many other Brits, are hungry for a break but don’t want to risk booking a trip abroad – then you need a staycation. All (well, nearly all) the benefits of a holiday without having to gamble on whether your destination will be moved to the red list, a staycation in the UK is a great way to still get away and rest this year. And as the weather gets cooler and the days get shorter, there’s still a lot of opportunities to have a relaxing few days off. 

When it comes to booking a staycation in the UK, there’s more than you think to think about. From your transport there to who’s going to look after the cat, this is the ultimate checklist for booking a staycation in the UK. 

Table of Contents

So, now you know what’s in store, let’s get right into the steps for booking the ultimate staycation in the UK!

Organise Your Dates

First things first – when are you going on your UK staycation? Whether you’re going away for an anniversary or birthday, or just when the two of you are free, set your dates first. This will help to narrow down your options, and can affect things further down this list such as weather and location. 

Once you’re set on the ‘when’ part, you can begin your search with a clear goal. Now, I don’t mean to make this process seem like a tonne of work. Holidays are fun – but the reality is that booking them isn’t always easy. So getting these kinds of things straight before we begin our search is the best way to set ourselves up for success!


Decide a Budget

Next, it’s time to decide how much you want to spend on your staycation in the UK. Depending on how long you’re planning to be away, how you’re travelling, and other factors, your budget will look different for each individual.

Aspects of your budget to consider:

  1. Accommodation
  2. Transport
  3. Spending money
  4. Food 
  5. Activities

With prices of staycations in the UK skyrocketing after we came out of lockdown, holidaying in the UK is working out to be more expensive than it used to be. Pre-Covid, going somewhere in the UK for your summer holiday was considered a much more affordable option, thanks to the savings that could be made on flights. However, there’s a lot of money to be made in the staycation holidays game now, which has seen prices increase a lot. An investigation by Which reported that prices had gone up on average by 35%!

With this in mind, when it comes to deciding your budget, you might want to consider padding it out a little if you can. And of course, depending on how long you’re going to stay (which you would have already decided in the previous step), your budget will need to reflect that.

Choose a Location

This is one of the most exciting parts of the staycation process! This might be a really easy step if there’s somewhere that’s been on your list for a while. If, however, you don’t have a destination in mind yet, then now is the time to pick where you want to go for your staycation. 

Great staycation ideas in the UK:


From St Ives to Penzance, Cornwall is one of the most idyllic places in the whole of the UK. Although, be warned that it’s also one of the most expensive places to go to, not to mention far – that 6-hour drive from London will need a lot of pit stops! But, it’s all worth it, because if you’re craving that seaside air and breathtaking views, then Cornwall is the place for you.

Plus, Cornwall is said to be beautiful (and sunny!) even in the autumn! So if you’re planning to get away in October or November, you can still get a little bit of sun on your staycation. 

The Peak District

An underrated area of the UK, the Peak District is a beautiful place to visit for a staycation. If you like long walks and cosy cottages, then you should give this northern gem a try. There’s nothing like spending a few cold nights in a cosy cottage!

The Scottish Highlands

Beautiful greenery, majestic castles and fresh countryside air – the Scottish Highlands have it all. For those wanting to really get far away, Scotland has some real hidden gems when it comes to staycations. If you don’t know where to start, check out this list of the best spots in Scotland.

Book Time Off

If you’re going on a long weekend or want to book a mid-week staycation for a more budget-friendly break, you’ll likely need to book time off work. So get those holiday requests in, and cross your fingers if you’re booking something last minute!

Pick Your Search Engine

Airbnb isn’t the only place to book a UK staycation. In fact, in reality, there are a lot of different accommodation options when you’re booking a staycation in the UK.

For Hotels

If you want that bit of luxury on your staycation and don’t want to worry about doing the dishes and cleaning up, then you can book a hotel! In the colder weather, hotels can also feel a bit warmer and cosier. is a cult favourite for holidaymakers, where you’ll find a combination of independent hotels, boutique picks and larger chains. 


Another of the more famous hotel booking sites is Trivago, where you can find great last-minute deals and hidden gems. 

Secret Escapes

For those looking for boutique hotels at great prices, Secret Escapes is the site for you. A lot of their deals also include things like spa treatments and sometimes, experiences. 

Book Direct 

Always been a fan of Hilton or Marriott? Then book directly with them for competitive rates!

For Homestays and Rentals


We couldn’t not include Airbnb on this list. With thousands of listings for any budget and a great user experience, booking with Airbnb is fuss-free and easy.


Vrbo is a newer holiday rental website, specialising in luxury getaways and family-friendly rentals. 

Plum Guide

For luxury homestays, definitely give Plum Guide a try. They apparently vet each and every one of their properties so you can enjoy a seamless experience.

Again, offers a range of homestays too!

For Unique Stays

Kip Hideaways

Kip Hideaways is a site dedicated to finding unique, utterly Instagrammable hideaways. All you have to do is become a member and enjoy a perfect hideaway!

Want to glamp under the stars or stay in a treehouse for your UK staycation? Coolstays has got you covered. 

Work Out Your Route

Once you’re set on where you’re going, it’s time to figure out how to get there. Knowing how long it’ll take you to arrive at your destination gives you crucial information to plan your trip – like what time you’ll need to leave to make the most of your booking. A simple Google Maps search will suffice here (thank you technology!) so that you can factor in travel time into your itinerary.

If it’s too complex or long winded to get to a certain destination, this might be the point where you go back to the drawing board (or step 3) and reassess where you want to go.

Book Your UK Staycation

Once you’ve found your dream accommodation, it’s time to book it! Remember, with some hosts on Airbnb, you need to submit a request to book their place before the reservation is confirmed, so try to get in there as soon as you can to avoid losing out to another eager holidaymaker. 

After booking, it’s always good to make sure you have your confirmation email and reservation reference handy in case anything changes or you need to provide proof of reservation.

Organise Travel Arrangements

Next, it’s time to sort out how you’ll get there. Each method comes with its own requirements and costs, so let’s look at them in a little more detail.


If you own a car or are able to rent one, driving is a much more relaxed way of travelling. You get to decide the music, temperature and speed – the only downside is the driving itself! But road trips are always fun, and cost-effective too.

However, it is worth noting that even if you own a car and you’re going to drive, it doesn’t mean you won’t need to prepare in any way for your staycation. If your accommodation is more than a few hours away, then you have a long drive ahead of you. It’s a good idea to make sure your MOT and servicing are all up to date, as well as making sure things like tire pressure and screen wash are all in working order.


Whether you use National Rail or Trainline, if you’re taking the train, it’s pretty easy to book your route. Remember to add on any railcards and see if you qualify for any discounts!


Coaches, although a long-winded way to travel, is much more cost-effective than trains. Plus, many coaches nowadays have had a revamp, including things like air conditioning and phone charging facilities onboard. So if you’re looking to stick to a lower budget, consider travelling by coach!


Although planes aren’t the most eco-friendly way to travel, if you need to get to the other end of the country then flying may be a viable option for you!

Take Out Travel Insurance

You’re probably thinking: ‘Travel insurance? For a staycation?? I thought that was just for medical cover abroad!’

Travel insurance does include healthcare costs while you’re abroad, but it also covers you for any cancellations or errors made by your accommodation or transport provider! So it’s worth looking into when you’re going on a staycation. Especially with the uncertainty that Covid has brought into pretty much every area of our lives, being covered for cancellations can save a lot of hassle in the future. 

Check the Weather

Oh, the unpredictability of British weather. Because we’re talking about a staycation in the UK during the autumn and winter months, it’s a given that it’s not exactly going to be sunny when you go away. But checking the weather is still a good move – no one wants to go for a staycation in a blizzard or torrential rain!

Book your House/Pet-Sitter

Now you’ve got a staycation in the UK to look forward to, it’s time to organise what you’ll leave behind. If your plants need watering or the dog needs walking but you don’t have any family or friends nearby who can do these things for you, then don’t panic. There are quite a few options when it comes to housesitters and petsitters too. 

For housesitters, try:

  1. Gumtree
  2. Mind My House
  3. SitMyHouse
  4. Trusted Housesitters

For petsitters, try:

  1. PawShake
  2. Nomador
  3. Rover 

Having someone to pop in to make sure everything’s okay can give you that extra peace of mind so that you can focus on having a good time!

See What’s Around

To make the most of your time on your staycation, do a little research before going to the area you’re visiting. Whether you’ve picked a place specifically for its landmarks, such as Bath or Cambridge, or you found a cool Airbnb to stay in, doing some research beforehand will mean you can plan your time efficiently. 

Here’s a list of the things to look out for when you’re doing your research:

  1. Restaurants 
  2. Bars 
  3. Attractions
  4. Walking routes
  5. Shops 
  6. Landmarks

Plan Your Itinerary

Now you know what’s around, it’s time to plan your days! If you’re looking to relax and watch movies all day, then you can just skip this step, but if you want to explore and take in the sights, then get planning. 

Sites like TripAdvisor and TimeOut have even made guides for certain areas, which are definitely worth a read.

Buy What You Need

Okay, so you might not be buying bikinis and shorts for a staycation in the UK, but there’s nothing stopping you from getting in the holiday spirit! Whether it’s a new set of comfies or some treats to eat while you’re away, go out and buy all the things you need to have a restful break. There’s no time like a holiday to treat yourself a little.


Nearly there now! As the all-important date of your staycation comes up, it’s time to get packing. It’s a pretty straightforward process, but we do have some tips on how to pack efficiently! Here’s a few now:

  1. Roll your clothes up – trust us, it takes up less space
  2. Take an extra bag for laundry – you’ll thank yourself later!
  3. Make a packing list – it’ll make the difference between remembering that comb and not!
  4. And if you’re hungry for more hacks, we all know there’s only one place to go: TikTok. 

Enjoy Your Staycation Holiday!

Congratulations, you’ve officially planned your very own staycation in the UK! There’s nothing left now but to count down the days and enjoy yourself when the time comes. 

We hope this checklist helped you out when planning your staycation – and if you need any extra recommendations, the enamoree team would be happy to answer them. Just get in touch or leave a comment below. Happy Staycations!

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