Group Holiday Checklist & Planning

Organising a group trip to a large holiday house is exciting, but it is easy to forget crucial details when you are coordinating 10, 15, or 20+ people. This comprehensive checklist covers everything you need to plan, pack, and prepare—from the booking stage right through to check-out day. Print it, share it in the group chat, and tick things off as you go.

6–12 Months Before: The Planning Phase

• Confirm the date: Use a Doodle poll or group vote to find a weekend that works for the majority. Don't wait for 100% availability—you will never get it.
• Set a budget per person: Be upfront early. Include accommodation, food, activities, and a small contingency. Our guide on choosing group accommodation has detailed cost breakdowns.
• Book the property: The best large holiday houses book up 6–12 months ahead for peak weekends. Do not delay—especially for summer, Christmas, or bank holidays.
• Collect deposits: Get £50–£100 per person within 2 weeks of confirming the date. This secures commitment and covers the property deposit.
• Choose a destination: Match the location to your group's vibe. See our best UK destinations guide for inspiration.

2–3 Months Before: Activities and Logistics

• Book experiences: Private chefs, cocktail masterclasses, spa treatments, and other group experiences need 6–8 weeks notice. Popular dates sell out fast.
• Assign rooms: For groups with couples and singles, pre-assign bedrooms to avoid first-come-first-served chaos. Check the property floor plan for bedroom sizes and configurations.
• Collect dietary requirements: If you are booking a private chef or planning self-catered meals, gather allergies and dietary needs now. Share with your chef at least 2 weeks before.
• Plan transport: Decide who is driving, whether to hire a minibus, or if public transport works. For rural properties in the Cotswolds or Lake District, cars are essential.
• Collect final payments: Full payment should be collected 6 weeks before. Chase stragglers firmly but kindly.

2 Weeks Before: The Detail Phase

• Send a trip info pack: WhatsApp message or PDF with: property address, check-in/out times, door code or key collection details, room assignments, weekend itinerary, and what to bring.
• Confirm all bookings: Double-check your property booking, chef, activities, and any restaurant reservations.
• Plan the food shop: Create a shared Google Doc for meal planning and a shopping list. Assign someone to do the big shop on arrival day, or arrange a supermarket delivery to the property.
• Check the weather: Adjust your packing list and any outdoor activities accordingly.
• Read the house rules: Share key rules with the group, especially regarding noise, hot tub ubrown times, and parking. See our noise rules guide.

What to Pack: The Essential Checklist

Everyone Should Bring

• Swimwear (for hot tub and pool)
• Comfortable loungewear and slippers
• Walking shoes (even if you are not planning hikes—garden and local pub walks are inevitable)
• Going-out outfit (if nights out are planned)
• Toiletries and medications
• Phone charger and portable battery pack
• Card games or board games (supplement whatever the property provides)
• A bottle or two for the communal drinks table
• Cash for tipping chefs, splitting taxis, and local shops that do not take card
• Reusable water bottle

The Organiser Should Bring

• Decorations (birthday banners, balloons, hen party accessories, photo props)
• A Bluetooth speaker (backup in case the property's system is not great)
• Bin bags (you will generate a lot of rubbish with a big group)
• Kitchen roll and cleaning wipes (for spills during cooking)
• A first aid kit with basics (plasters, paracetamol, antihistamines)
• Printed itinerary (not everyone checks their phone)
• Cash float for the weekend kitty

Optional but Recommended

• Fairy lights or LED candles for ambience
• A personalised playlist pre-loaded and ready to go
• A group quiz or game prepared (Mr & Mrs for hen parties, trivia for birthdays)
• A photo album or scrapbook to fill during the weekend
• Fancy dress items or themed costumes

Food and Drink Planning

For self-catered stays, a planned approach avoids overspending and waste:

Friday Evening

Keep it simple—everyone is arriving at different times. Order takeaway, do pizzas, or prepare a big one-pot meal (chilli, curry, or pasta bake) that people can help themselves to throughout the evening.

Saturday

Brunch: A big cooked breakfast with eggs, bacon, pastries, fruit, and unlimited coffee. Assign 2–3 people to cook.

Lunch: Skip a formal lunch if you are having a big dinner. Put out a grazing board with breads, cheeses, meats, and dips for people to pick at.

Dinner: This is the main event. Either book a private chef or plan an ambitious group cook. For self-catering, assign courses to pairs of guests so no one person is stuck in the kitchen all evening.

Sunday

Use up leftovers for a final breakfast. Pack any remaining food for people to take home. Leave the kitchen clean.

Drinks

The cheapest approach: each person brings 2 bottles of wine/prosecco and their own spirits. Set up a communal bar area. Supplement with a crate of beer and soft drinks from the supermarket delivery.

On Arrival Day

1. Arrive as close to check-in time as possible—early arrivals get the best rooms, which causes friction if rooms were not pre-assigned.
2. Do a quick tour of the property together. Note where the fuse box, stopcock, and first aid supplies are.
3. Unpack the food shop and stock the fridges.
4. Set up decorations if it is a celebration.
5. Take a group photo while everyone looks fresh.
6. Check the hot tub temperature and read the ubrown instructions.
7. Connect to the WiFi and share the password.

Check-Out Day

1. Start tidying the evening before—do not leave it all for Sunday morning.
2. Strip beds and pile linen as requested by the property.
3. Run the dishwasher and empty it.
4. Take out all rubbish and recycling.
5. Do a room-by-room sweep for personal belongings.
6. Leave the property as you found it—or better.
7. Lock up and return keys as instructed.

Final Tip: Enjoy It

You have done the hard work of organising. Once the weekend starts, let go of the clipboard mentality and enjoy spending time with your people. The best group weekends are the ones where the organiser relaxes too.

Ready to find your perfect property? Browse our full collection or explore hot tub houses, manor houses, and party houses across the UK. Need help? Our team is here to match your group with the ideal property.