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Beat the Rush: When to Book the Year’s Biggest Getaways
Published
4 March, 2026
Edited
24 September, 2026
The best time to book? Before everyone else, of course. Christmas, Thanksgiving, Spring Break, summer in Europe, it may feel like the distant future, but the best homes rarely stay available for long. Consider this your calendar cheat sheet for snagging the best of the best when it comes to high season and holiday stays. We’ve broken down when demand starts to build, and the sweet spot for booking each trip, so you can beat the rush and find a home that feels just right.
Christmas
You probably thought you’d outgrown dreaming of Christmas in the middle of summer. But trust us, tapping into your festive spirit early pays off. Book ahead to have your pick of the most magical homes, and one less thing to think about once the festive countdown begins.
We receive the most enquires:
September and October.
To beat the crowd:
Book from July through August.
Where to Stay: London
Christmas suits London. The lights are twinkling, the shop windows are dressed to the nines, and Kensington puts you close to it all. Brunswick Gardens II sleeps up to 10 across six bedrooms, with original details, art and antiques, and plenty of space to celebrate together. There’s even a second sitting room, should anyone need a strategic retreat after one too many mince pies.
Thanksgiving
From gathering the family to perfecting that pumpkin pie, Thanksgiving is already a game of logistics, so it pays to settle on your stay well in advance. Book ahead to find a home with enough bedrooms for the entire party, generous gathering spaces, and a kitchen ready for its biggest assignment of the year. Private chef or groceries delivered to your doorstep? We’ve got you covered.
We receive the most enquires:
July and November.
To beat the crowd:
Book in June.
Where to Stay: Colorado
A Rocky Mountain Thanksgiving comes with its own kind of abundance: big views, crisp air, and appetites sharpened by a day outside. In Telluride, The Peaks sleeps up to 12 across five bedrooms, with plenty of room for the whole family. There’s a game room for competitive relatives, and a hot tub for restoring diplomatic relations afterward.
Spring Break
Here’s one homework assignment you’ll want to finish early: booking spring break. Get it on the calendar before the New Year to beat the January crowd and give yourself somewhere sunny to dream about when winter starts to drag.
We receive the most enquires:
January.
To beat the crowd:
Book before the New Year.
Where to Stay: The Caribbean
If spring break is the reward for making it through winter, Turks and Caicos is the prize to keep your eye on. Set on Long Bay Beach, Kailoa Villa overlooks the Caicos Banks and sleeps up to eight across four bedrooms. The pool, tennis court, and direct beach access will keep everyone in your camp occupied; daily housekeeping makes sure nobody is working on vacation.
Euro Summer
Planning your European summer takes more than saving a few trattorias on your Instagram and hoping for the best. Start your search in winter and aim to have your bookings secured by January. The rosé can be spontaneous. The villa, less so.
We receive the most enquires:
January for Italy, April for London and the South of France.
To beat the crowd:
Book before the New Year.
Where to Stay: Italy
Tuscany in summer isn’t a hard sell. There are little towns to explore, chilled glasses of Vernaccia to drink, and some of the world's finest dining options to dig into. Once a 20th-century ruin, Villa San Gerolamo is now a striking five-bedroom retreat overlooking the hills of Crete Senesi, with room for up to 10 guests, plus a saltwater pool, hot tub, and gym.
