How to Boost Winter Bookings

Your Winter Booking Playbook: 6 Steps to Success

A property owner in Saint John, New Brunswick Canada, recently shared their struggle in a Skool community:

"Wondering if someone could give me some ideas on how to get my bookings up in Saint John, NB. Had no bookings in November and half the month vacant in December now."

If you’ve ever felt the sting of empty calendars during the slow season, you’re not alone. Whether you’re running a cozy ski chalet, a beachside retreat, or a cabin near hiking trails, slow bookings can be a frustrating challenge. The good news? With a few simple adjustments, you can transform your property into a must-visit winter destination.

Here are six practical strategies to help boost your winter bookings and keep your property thriving, no matter where it’s located.

1. Showcase Your Destination’s Unique Appeal

Every destination has something special to offer in winter—whether it’s Saint John’s snowy trails and Bay of Fundy views, the festive charm of ski towns, or the tranquil beauty of coastal areas in the off-season. Highlight what makes your location stand out.

Quick Action: Create a “Winter Escape” package with small but thoughtful perks like:

• A complimentary hot chocolate or locally sourced treat
• Late checkouts for relaxed mornings
• Discounts for nearby restaurants, ski rentals, or local attractions

Wherever your property is, focus on creating an experience that makes guests feel at home and excited to visit.

2. Update Your Listing for Seasonal Appeal

Your listing is often the first thing potential guests see—make sure it reflects your property’s winter charm.

• Photos: Highlight cozy features like fireplaces, snowy views, or holiday decor.
• Description: Use inviting language that captures the season, like: “Imagine unwinding with a warm drink by the fire after a day of exploring snowy trails or local winter markets.”
• Seasonal Keywords: Incorporate phrases like “cozy winter getaway,” “family-friendly holiday retreat,” or “perfect for snowy adventures.”

Quick Action: Take three new photos of your property that showcase its winter charm and update your listing today.

3. Get Your Property in Front of More Eyes

In a crowded market, visibility is key. Use these strategies to attract attention:

• Social Media: Share authentic photos or videos of your property’s winter setup—cozy indoor spaces, snowy landscapes, or festive touches.
• Ads: Target travelers in nearby cities with ads that highlight how easy it is to enjoy a winter escape.
• OTA Listings: Update your title and description with seasonal keywords to stand out.

Example Seasonal Titles:

• “Cozy Winter Retreat with Stunning Mountain Views”
• “Family-Friendly Holiday Escape Near Snowy Trails”
• “Relaxing Coastal Getaway Perfect for Winter Walks”

Quick Action: Update your listing title with a seasonal hook and post a short video of your property on social media today.

4. Adjust Pricing with Confidence
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Winter months often come with lower demand, so flexible pricing is key to attracting bookings.

• Dynamic Pricing Tools: Platforms like PriceLabs or Beyond Pricing use AI to adjust rates based on local demand, events, and competitor pricing—ensuring your property remains competitive while maximizing revenue.
• Seasonal Offers: Deals like “Stay 3 Nights, Pay for 2” or midweek discounts can catch the attention of budget-conscious travelers.

Quick Action: Test a promotional offer, such as a 15% discount for midweek stays, and track its impact using your booking platform’s analytics.

5. Collaborate with Local Businesses

Working with local partners can enhance your property’s value while strengthening community ties.

• Team up with restaurants, shops, or attractions to create bundled packages or exclusive discounts.
• Collaborate with tourism boards to feature your property in seasonal promotions.

For example, if you’re near a ski town, offer discounted lift tickets in partnership with the resort. If your property is in a coastal area, team up with a local seafood restaurant for a “Winter Dinner Special.”

Quick Action: Reach out to one local business or tourism board this week to explore a partnership opportunity.

6. Gather Insights from Guests and Locals

Your past guests and local community are invaluable resources for fresh ideas.

• Past Guests: Ask what they loved about their stay and what would make their winter experience even better.
• Locals: Are there hidden gems, winter activities, or unique traditions in your area that you could promote?

AI-powered survey tools can make gathering feedback quick and easy, helping you spot trends and implement improvements.

Quick Action: Use a free survey tool to ask your past guests one key question: “What would make our property your go-to winter escape?”

Recap

1. Showcase Your Destination: Highlight your area’s unique winter attractions and offer thoughtful perks.
2. Update Your Listing: Use seasonal photos and keywords to make your property stand out.
3. Boost Visibility: Leverage social media, ads, and OTA updates to reach more travelers.
4. Adjust Pricing: Use dynamic pricing or creative offers to attract bookings without undervaluing your property.
5. Partner Locally: Collaborate with businesses or tourism boards to add value and reach new audiences.
6. Get Feedback: Learn from guests and locals to uncover new ways to appeal to winter travelers.

Winter travelers are out there, searching for their perfect escape. Whether it’s updating your listing, experimenting with pricing, or creating a unique experience, taking action now can set your property apart.

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Got a challenge you need help with?

Join our Skool community, share your story, and your property might just be featured with creative strategies to turn things around!

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