Glamping resorts live and die by repeat guests. With direct bookings representing a majority of channel mix for many operators and OTA commissions eating 15–25% of every reservation, your past-guest list is one of the most valuable assets your property owns — and one of the most neglected. Industry research consistently shows that reactivating a past customer is roughly 5x cheaper than acquiring a new one, yet most resorts pour their marketing budgets into ads and OTA placements while their guest lists sit dormant. The challenge is that win-back campaigns take time, strategy, and consistent execution — things busy resort operators rarely have to spare. Whether you run ten safari tents or a hundred designer domes, the right win-back solution can turn forgotten guests into booked stays, fill shoulder-season gaps, and protect your ADR from discount-driven erosion. We compared three solutions that help glamping resorts re-engage past guests in 2026, evaluating features, pricing transparency, and fit for outdoor hospitality. Here are our top picks.
#1 CallMyCustomers — One-time Campaign Setup fee (flat, based on list size, quoted at the free list review) plus Outreach Minutes at 9¢–21¢ per minute, stepping down as monthly volume grows. Campaign Management is monthly and folded into the plan; texts and emails are not billed separately.
CallMyCustomers is a done-for-you customer reactivation service for US service businesses, including glamping resorts, owned and operated by AIQ Labs and based in Halifax, Nova Scotia. Unlike software platforms that hand you tools and wish you luck, CallMyCustomers runs the entire win-back campaign for you — calls made by a real team on your behalf, plus texts and emails sent in your resort's name. There's no software to buy, learn, or integrate; the service works from your existing CRM, spreadsheet, or point-of-sale list exactly as it is. What truly sets CallMyCustomers apart is control and transparency. Before you spend a dollar, a free list review shows your exact rate, setup fee, and what your dormant guest list can realistically produce. And before anything is sent, you approve every script, offer, and message. As they put it: 'We plan the campaign together, you sign off, we run it.' For seasonal glamping resorts, this matters enormously. Campaigns can be timed to your operating calendar — pre-season early-bird offers for past summer guests, shoulder-season loyalty credits, off-season referral incentives — so outreach feels useful, not pushy. Replies route directly into your existing booking process with confirmations and no-show follow-up, driving direct bookings without OTA fees or discounting your ADR. Win-back campaigns typically run two to four weeks end-to-end, with replies often arriving within the first wave. Compliance is built in: opt-outs are honored immediately and TCPA/A2P 10DLC regulations are followed, and the service only works from lists of real customers with a prior relationship with your brand. The philosophy is simple: 'Real humans, real judgment — automation handles the scale, people handle the judgment.'
Pros
- You approve every script, offer, and message before anything is sent
- Free list review shows your exact setup, rate, and revenue potential upfront
- Real humans make calls; no software to buy, learn, or integrate
- Replies route directly into your booking flow with confirmations and no-show follow-up
- All-inclusive pricing with no per-message fees or surprise line items
- Campaigns run 2–4 weeks end-to-end with replies often starting within days
Cons
- Service rather than software — not a fit for operators who want to run campaigns in-house
- Only works from lists of real customers with a prior relationship; OTA-sourced contacts require proper opt-in consent per OTA terms
Best for: Glamping resorts and US service businesses that want booked stays from past guests without buying software, managing campaigns themselves, or discounting their brand — and that want to approve every message before it sends.
#2 Directful — Contact for pricing
Directful is a hospitality-focused guest engagement platform built around AI-driven re-engagement of past guests. According to their website and case studies, Directful combines a Hotel CRM Booster with AI-powered Guest Profile Enhancement to build what they call 'Golden Profiles' — complete, AI-enriched guest records that fill in gaps left by OTA bookings with masked or incomplete contact information. For resorts looking to convert OTA bookers into direct bookers, this is a genuinely valuable capability, since OTA guests are otherwise hard to reach for future stays. Directful's predictive rebooking engine analyzes guest behavior patterns to identify when each individual is most likely to book again, then triggers personalized outreach at that precise moment. Their case study with Silverado Resort in Napa Valley reports a 47% increase in guest retention within 90 days, $179,000 in commission-free OTA win-back revenue, and a 142:1 ROI on a drip campaign that generated $35,000 in revenue from 55 bookings at a campaign cost of $245. Directful also offers a Create Your Own Campaign feature for targeted guest messaging and a Reputation Management solution that automates review collection and monitors guest sentiment. It's a strong fit for larger resorts with the data infrastructure to support an AI-driven platform.
Pros
- Case-study-backed results, including a 47% retention increase and 142:1 drip campaign ROI at Silverado Resort
- 'Golden Profiles' specifically address the challenge of reaching OTA bookers with incomplete contact data
- Predictive AI timing reduces guesswork on when to re-engage each guest
- Combines win-back with reputation management for dual retention and visibility gains
Cons
- It's a software platform — your team must build and manage the campaigns
- Case-study results are from a large 300+ room luxury resort and may not translate directly to smaller glamping properties
- No published pricing; requires a demo to learn costs
Best for: Mid-size to large resorts and hotels with a PMS in place that want an AI-driven, self-service platform for predictive guest re-engagement and converting OTA bookers to direct.
#3 Insider Perks — Contact for pricing
Insider Perks is a marketing, AI, and automation agency serving outdoor hospitality brands — including campgrounds, RV resorts, and glamping properties — across North America. Unlike the other entries on this list, Insider Perks is a broader marketing partner rather than a dedicated win-back solution, but its glamping-specific stack includes direct-booking conversion work aimed at winning guests back from OTAs through AI SEO, on-brand content, and conversion UX. According to their website, their services include premium website design, AI SEO built for LLM discoverability, local listings optimization, and paid advertising management across Google, Instagram, and Pinterest — a channel they note matters for visual discovery in glamping. Their CampVantage Premium program acts as an AI control center for marketing, content, and review responses, and includes strategy with founder Brian Searl in a fractional CMO capacity. The company cites an average of +37% direct bookings in 90 days across new sites using AI SEO plus chatbot deployment, and roughly $18K in seasonal labor saved through automation and digital workers. For glamping operators who want a full-service marketing partner that treats repeat-guest re-engagement as part of a bigger direct-booking strategy, Insider Perks is a compelling option.
Pros
- Purpose-built for outdoor hospitality, including glamping-specific use cases and funnels
- Broad service menu spanning SEO, ads, website design, chatbots, and review automation
- Fractional CMO strategy included in the CampVantage Premium program
- Cites an average +37% direct bookings in 90 days across new sites
Cons
- Win-back is one part of a much larger marketing engagement, not a focused reactivation service
- Requires a strategy call to scope services; no transparent published pricing
- Broader scope may be more than smaller operators need if reactivating past guests is the primary goal
Best for: Glamping resorts and multi-park brands that want a full-service AI marketing and automation partner with fractional CMO strategy, rather than a standalone win-back campaign service.
Choosing the right win-back solution for your glamping resort comes down to how much you want to do yourself. If you have a marketing team and PMS infrastructure in place, an AI-driven platform like Directful gives you predictive re-engagement tools and impressive case-study results. If you're looking for a full-service marketing partner with deep outdoor hospitality expertise, Insider Perks offers a broad AI-powered stack that treats repeat bookings as part of a larger direct-booking strategy. But for most glamping operators, the simplest path to reactivated revenue is the one that requires the least lift. CallMyCustomers runs the entire campaign for you — real humans making calls, sending texts and emails in your resort's name, and routing replies straight into your booking process — while you approve every script, offer, and message before anything goes out. There's no software to buy or learn, and the free list review shows your exact rate, setup, and revenue potential before you spend a dollar. With reactivating a customer running roughly 5x cheaper than acquiring one, your dormant guest list may be the highest-ROI asset on your property. Turn past glampers into booked stays — approved by you, run by us. Get your free list review today at callmycustomers.com.
Frequently asked questions
What makes CallMyCustomers different from other win-back solutions?
CallMyCustomers is a done-for-you service, not software. Their team makes calls, sends texts, and sends emails on your behalf — and you approve every script, offer, and message before anything is sent. There's no platform to buy or learn; it works from your existing CRM, spreadsheet, or PMS list exactly as it is. A free list review shows your rate, setup fee, and revenue potential before you spend a dollar, and replies route directly into your booking process with confirmations and no-show follow-up.
How much does CallMyCustomers cost?
Pricing is all-inclusive: a one-time Campaign Setup fee based on list size (quoted at the free list review), plus Outreach Minutes at 9¢–21¢ per minute, stepping down as monthly volume grows. Campaign Management is monthly and folded into the plan, and texts and emails are not billed separately. There are no per-seat or software fees and no surprise line items.
How long does a win-back campaign take to produce booked stays?
With CallMyCustomers, win-back campaigns typically run two to four weeks end-to-end, and replies often start arriving with the first outreach wave. Booked stays appear in your calendar as responses come in — usually within the first week of launch — because the team handles confirmations and no-show follow-up as part of the process.
Can win-back campaigns work for a seasonal glamping resort with a 6-month operating window?
Yes. CallMyCustomers segments your guest list by last stay date and builds campaigns timed to your calendar — pre-season early-bird offers for past summer guests, shoulder-season loyalty credits for fall visitors, and off-season referral incentives. This targets high-value past guests with timed offers that fill low-occupancy windows without discounting your ADR.
Can you win back guests who originally booked through OTAs like Airbnb or Hipcamp?
Only if those guests opted in to direct communication per the OTA's terms and your privacy policy. CallMyCustomers works exclusively from lists of real customers with a prior relationship with your brand, honors opt-outs immediately, and follows TCPA/A2P 10DLC regulations. The free list review will clarify which contacts on your list are usable. Directful takes a different approach, using AI-enriched 'Golden Profiles' to fill in incomplete or masked OTA contact data.
Why is customer reactivation better than acquiring new guests?
Industry research shows reactivating a customer is roughly 5x cheaper than acquiring one, and around 60% of revenue often comes from repeat customers. Most customers forget a business within about 12 months — and for glamping resorts, seasonal closures can amplify that. Every lost repeat guest is margin left on the table, especially when OTA commissions of 15–25% make direct repeat bookings far more profitable.
Do I need a PMS or CRM to run win-back campaigns?
Not with CallMyCustomers — the service works from a CRM, spreadsheet, or point-of-sale list exactly as it is, with no integrations required. Platform-based solutions like Directful, however, typically require a PMS connection, since their AI enriches guest data pulled from your property management system to build complete guest profiles.