How to maximise holiday let bookings this winter: Proven methods to fill your calendar during low season

Marketing tips

How to maximise holiday let bookings this winter: Proven methods to fill your calendar during low season

5 Dec 2025

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By Amanda Sanders

Winter can still be a profitable time of year for holiday let owners, but only if you have a clear strategy in place. With booking windows shortening by roughly 4-6% based on data from Sykes Holiday Cottages, hosts must be ready to capture interest fast. Shorter lead times mean travellers are browsing later, comparing more options and making quicker decisions once they commit. This guide explains how to use dynamic pricing for festive peaks, how to package winter experiences that convert browsers into bookings, how to prepare your property for cold weather guests and how to market effectively to late bookers. You will also learn how Travelnest helps hosts secure an average of six extra bookings and a 21% rise in winter revenue through smart pricing and multi channel distribution.

Why winter matters for your holiday let

Recent VisitBritain data shows that domestic tourism remains a large and valuable market, with British residents taking over 100 million overnight trips and spending nearly £33 billion within Great Britain in 2024, even though trip volumes have softened compared to 2022 and 2023.

Winter also brings unique opportunities that do not exist at other times of year, such as:

  • Christmas market breaks

  • New Year celebrations

  • Winter walking trips

  • Romantic weekends

  • Cosy escapes with firewood, hot chocolate and indoor comforts

This makes winter an ideal time to rethink your pricing, positioning and marketing so you can attract a broader range of guests.


How to use dynamic pricing for winter success

Dynamic pricing ensures that your nightly rates reflect real time demand. Prices should rise for high intent dates such as Christmas and New Year, then adjust for quieter mid week periods. This keeps your property competitive while also protecting your earnings.

Key tips for winter pricing

  • Review historic trends for festive peaks.

  • Offer slightly lower entry prices for early winter, then increase them gradually as dates fill.

  • Monitor competitor rates and occupancy so you remain attractive to last minute bookers.

  • Add short stay options for guests seeking two to three night breaks.

With Travelnest Smart Pricing, hosts can automate these adjustments. 


How to create winter experience packages that convert

Travellers increasingly look for memorable stays rather than simply accommodation. Packaging winter themed experiences can make your property stand out in busy marketplaces.

Experience ideas to add to your listing

  • A festive welcome basket with mulled wine, mince pies or locally sourced treats

  • Discount codes or guides to nearby Christmas markets

  • New Year celebration bundles such as prosecco, sparklers or a late check out

  • Cosy night in kits for couples or families

  • Winter walking maps and recommendations for local trails

Your Travelnest property expert can also help you shape seasonal packages based on your location and guest profile.


How to optimise your property for winter guests

Winter guests value warmth, comfort and convenience. Small changes can improve reviews, increase occupancy and raise the likelihood of repeat bookings.

Practical winter upgrades

  • Clear instructions for heating controls

  • Extra blankets, throws or thick duvets

  • A stocked firewood basket if you have a wood burner

  • Soft lighting for a cosy atmosphere

  • Weather resistant outdoor mats and boot trays

  • Clear information on local winter attractions and travel conditions

Guests often mention thoughtful touches in reviews, which strengthens your ranking on travel sites.


How to attract late bookers with stronger marketing

Shorter booking windows mean guests are browsing closer to their travel dates. This makes visibility and messaging even more important.

Marketing tactics that work in winter

  • Refresh your listing title and description with seasonal keywords such as cosy winter getaway or Christmas market break

  • Update your photo gallery to include winter ready shots such as soft throws, firelight, festive decor and winter scenes if available

  • Offer last minute discounts on low demand dates

  • Use social media to highlight availability gaps, special offers and seasonal experiences

  • Emphasise flexible cancellation where possible to build guest confidence

Travelnest distributes your property across over 30 top booking sites, giving you global exposure.


How Travelnest helps hosts maximise winter revenue

Travelnest was designed to simplify hosting and increase visibility for every property. During the winter months, our features become even more valuable.

Benefits for winter performance

  • Smart Pricing adjusts rates automatically for seasonal shifts

  • Multi channel distribution promotes your property across leading travel sites

  • Property experts provide tailored guidance for improving winter appeal

  • Hosts using Travelnest achieve on average six additional bookings in winter and a 21% increase in revenue during quieter months

These features give you a competitive advantage that helps you fill your calendar even when market activity slows.


Final checklist for a strong winter strategy

To maximise bookings this winter, make sure you:

  • Activate dynamic pricing and review your seasonal rate plan

  • Add winter experience packages to create more value for guests

  • Prepare your property with thoughtful winter touches

  • Update your listing, images and keywords for seasonal search

  • Promote last minute availability and stay flexible

  • Use Travelnest tools and expert support to strengthen performance

With the right approach, winter can become one of your most profitable seasons.

How to maximise holiday let bookings this winter: Proven methods to fill your calendar during low season

Start, promote, and manage your rental property with Travelnest

  • Global exposure

  • Guest messaging

  • Payment processing

  • Smart pricing

  • Calendar sync

  • Travelnest Direct

  • On-hand support

  • Management dashboard

Start, promote, and manage your rental property with Travelnest

  • Global exposure

  • Guest messaging

  • Payment processing

  • Smart pricing

  • Calendar sync

  • Travelnest Direct

  • On-hand support

  • Management dashboard

Start, promote, and manage your rental property with Travelnest

  • Global exposure

  • Guest messaging

  • Payment processing

  • Smart pricing

  • Calendar sync

  • Travelnest Direct

  • On-hand support

  • Management dashboard

Start, promote, and manage your rental property with Travelnest

  • Global exposure

  • Guest messaging

  • Payment processing

  • Smart pricing

  • Calendar sync

  • Travelnest Direct

  • On-hand support

  • Management dashboard