Marketing tips
5 reasons holiday rental owners should offer flexible stays in winter
17 Dec 2025
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By Amanda Sanders
Winter can be a challenging time for holiday rental owners. With shorter days, colder weather, and reduced leisure travel, occupancy rates typically drop compared to the bustling summer months. However, this quieter period presents a unique opportunity to attract guests by offering flexible stay options that meet their specific winter needs. By adapting your rental strategy to include shorter stays, weekday bookings, extended check-out times, seamless self-check-in, and last-minute availability, you can transform the traditionally slow winter season into a profitable period. Here's why flexibility is your secret weapon for winter success.
Reason 1: Short stays capture spontaneous winter bookings
Winter weather is unpredictable, and so are travel plans. Guests are more likely to book spontaneous getaways when they see a clear weather window or have an unexpected free weekend. By accepting short stays of just one or two nights, you open your property to this valuable market segment.
Short winter breaks are particularly popular for:
Weekend city escapes when the weather improves
Quick ski trips or winter sports weekends
Romantic getaways around Valentine's Day
Last-minute family visits during school holidays
Travelnest's flexible booking settings make it simple to adjust your minimum stay requirements for winter months. Our property experts can help you identify the optimal minimum stay length based on your location and target market, ensuring you capture more bookings without compromising profitability.
Reason 2: Weekday stays tap into business and leisure blend travel
The rise of remote working has created new travel patterns, with many professionals choosing to work from scenic locations during quieter weekdays. Winter weekday stays offer excellent value for these "bleisure" travellers who want to escape their home office for a change of scenery.
Weekday winter bookings often come from:
Remote workers seeking inspiring workspaces
Couples planning mid-week romantic retreats
Retirees avoiding weekend crowds and higher prices
Business travellers extending their trips for leisure
Offering attractive weekday rates through Travelnest's smart pricing tools helps you fill those traditionally quiet Monday to Thursday nights. Your dedicated property expert can advise on competitive weekday pricing strategies that attract business while maintaining healthy profit margins.
Reason 3: Late check-outs enhance guest satisfaction and reviews
Winter travellers often face unpredictable weather conditions and transport delays. Offering flexible check-out times, particularly late check-outs, can significantly improve the guest experience during these challenging months.
Benefits of flexible winter check-outs include:
Allowing guests to wait out poor weather conditions
Reducing stress around tight travel connections
Providing extra value that encourages positive reviews
Differentiating your property from less flexible competitors
Industry research consistently shows that flexible policies significantly enhance guest satisfaction and review scores. Travelnest's automated messaging system can communicate your flexible check-out policies clearly to guests, while our property management tools help you coordinate with cleaning teams to accommodate these arrangements.
Reason 4: Self-check-in removes barriers for winter arrivals
Winter weather can make travel times highly unpredictable. Flights get delayed, trains are cancelled, and road journeys take longer than expected. Self-check-in eliminates the stress of coordinating arrival times and removes a significant barrier to booking during uncertain winter months.
Self-check-in advantages for winter bookings:
Guests can arrive at any time without worrying about host availability
Reduced cancellations due to travel delays
Appeals to international travellers adjusting to different time zones
Provides contactless arrival option, which many guests still prefer
Travelnest integrates with leading smart lock providers and keypad systems, making self-check-in setup straightforward. Our customer support team provides guidance on the best self-check-in solutions for your property type and budget.

Reason 5: Last-minute availability captures winter deals seekers
Winter travellers are often bargain hunters, looking for great deals on accommodation. By keeping your calendar open for last-minute bookings and offering attractive rates for short-notice stays, you can capture this price-conscious market segment.
Last-minute winter bookings typically come from:
Couples planning spontaneous romantic weekends
Groups organising last-minute winter sports trips
Solo travellers seeking off-season exploration opportunities
Through platforms like Booking.com's promotional tools, Travelnest hosts can set up automated discounts that increase as your check-in date approaches, ensuring you fill vacant nights rather than leaving them empty. Your property expert can recommend the best last-minute pricing strategy based on your local market conditions and historical booking patterns.
Transform your winter strategy with Travelnest
Implementing flexible stay options doesn't mean sacrificing profitability or control over your property. The key is finding the right balance of flexibility that works for your specific situation and guest market.
Travelnest's comprehensive property management platform makes it easy to implement these flexible strategies while maintaining operational efficiency. Our automated systems handle guest communications, coordinate check-in processes, and manage pricing adjustments, while your dedicated property expert provides ongoing strategic guidance.
From dynamic pricing tools that optimise rates for different booking scenarios to automated messaging sequences that communicate your flexible policies clearly, Travelnest provides the technology and expertise you need to succeed in the competitive winter rental market.
Don't let winter be your quiet season. Embrace flexibility and watch your occupancy rates climb, even when the temperature drops. Contact your Travelnest property expert today to discuss how these flexible stay strategies can work for your specific property and market.
