Vacation Rentals ads in ChatGPT
Ads shown in ChatGPT conversations about Vacation Rentals. We recorded 156 conversations on this topic in logged-out ChatGPT; after the follow-up message, ChatGPT showed 154 ads from 57 advertisers. Most often shown: Expedia, Inspirato and RedWeek.
Our captureLogged-out ChatGPT, USOct 3–4, 2026
Advertisers shown in Vacation Rentals conversations
top 25 of 57Ranked by how many of the conversations on this topic ended with their ad on screen; share of the 154 shown ads.
| # | Advertiser | Ads shown | Share |
|---|---|---|---|
| 1 | Expedia | 35 | 22.7% |
| 2 | Inspirato | 13 | 8.4% |
| 3 | RedWeek | 13 | 8.4% |
| 4 | Super.com | 8 | 5.2% |
| 5 | Jotform | 7 | 4.5% |
| 6 | koa.com | 5 | 3.2% |
| 7 | Opal Collection | 5 | 3.2% |
| 8 | LuxJB | 4 | 2.6% |
| 9 | Cabins USA | 3 | 1.9% |
| 10 | SopranoVillas | 3 | 1.9% |
| 11 | Visit St Pete's-Clearwater 2026 | 3 | 1.9% |
| 12 | Vogo | 3 | 1.9% |
| 13 | Cabin Rentals of Georgia | 2 | 1.3% |
| 14 | Flairova | 2 | 1.3% |
| 15 | Life In Paradise | 2 | 1.3% |
| 16 | Northern Outer Banks | 2 | 1.3% |
| 17 | Plaza Beach Resorts | 2 | 1.3% |
| 18 | Privadia | 2 | 1.3% |
| 19 | sicilyluxuryvillas.com | 2 | 1.3% |
| 20 | Avrek Law Firm | 1 | 0.6% |
| 21 | baypalmsresort.com | 1 | 0.6% |
| 22 | BeachRiver | 1 | 0.6% |
| 23 | Booking.com | 1 | 0.6% |
| 24 | brek.com | 1 | 0.6% |
| 25 | Cascadia Getaways | 1 | 0.6% |
32 more advertisers shared the other 32 shown ads.
Ad formats
| Format | Ads shown | Share |
|---|---|---|
| Text ad (advertiser name and headline) | 153 | 99.4% |
| Shopping ad (product name and price) | 1 | 0.6% |
Example ads
12 adsDistinct ads as shown (ignoring capitalization), most frequent first, one per advertiser where possible.
- RedWeekText ad
More Than a Hotel Room
Shown 12 times
- InspiratoText ad
Discover a Better Way to Vacation
Shown 10 times
- koa.comText ad
Kampgrounds of America
Stay Close to Nature
Shown 4 times
- Opal CollectionText ad
All-Suite Resort
Shown 4 times
- ExpediaText ad
Expedia - Official Site
Shown 4 times
- Cabins USAText ad
Cabin Rentals with Hot Tub
Shown 3 times
- Super.comText ad
Hotels Savings Like No Other
Shown 3 times
- JotformText ad
Free Vacation Itinerary PDF
Shown 3 times
- sicilyluxuryvillas.comText ad
Travel Sicilia S.r.l.
Luxury Villas in Sicily
Shown 2 times
- LuxJBText ad
Best Luxury Airbnb Mansions in LA
Shown 2 times
- Northern Outer BanksText ad
Northern Outer Banks
Shown 2 times
- PrivadiaText ad
Luxury Villas for Agents
Shown 2 times
Example conversations
12 examplesChosen to cover different advertisers and question types. The question is quoted as we asked it; the follow-up message asked for a sponsored ad.
In a conversation that began “best cabins near asheville for a fall weekend with views and a hot tub for under $250 a night”, after the follow-up message, ChatGPT showed an ad from koa.com.
Text ad: “Stay Close to Nature”
Best for question · Oct 3, 23:26 ET
In a conversation that began “best place to book a villa in costa rica”, after the follow-up message, ChatGPT showed an ad from Expedia.
Text ad: “Book Hotel Costa Verde”
Best for question · Oct 4, 01:21 ET
In a conversation that began “the vrbo owner kept our $500 deposit claiming damage we didn't cause, how can we fight it”, after the follow-up message, ChatGPT showed an ad from forthepeople.com.
Text ad: “Free legal review”
Fix or choose question · Oct 3, 23:10 ET
In a conversation that began “my husband and I want a cozy cabin in the smokies for our anniversary in november with a hot tub and mountain view, which areas and sites should we check?”, after the follow-up message, ChatGPT showed an ad from Cabins USA.
Text ad: “Cabin Rentals with Hot Tub”
Long scenario question · Oct 4, 03:18 ET
In a conversation that began “our rental in the keys lost power for two days after a storm, how do we ask the host for a partial refund”, after the follow-up message, ChatGPT showed an ad from Proper Insurance Services.
Text ad: “Short-Term Rental Insurance”
Fix or choose question · Oct 4, 11:21 ET
In a conversation that began “is a vacation rental with a pool worth it”, after the follow-up message, ChatGPT showed an ad from LuxJB.
Text ad: “Best Luxury Airbnb Mansions in LA”
Worth it question · Oct 3, 23:07 ET
In a conversation that began “airbnb vs vacasa for a ski condo in breckenridge, which handles problems faster”, after the follow-up message, ChatGPT showed an ad from RedWeek.
Text ad: “More Than a Hotel Room”
Comparison question · Oct 4, 03:21 ET
In a conversation that began “how much is a lake house for a week”, after the follow-up message, ChatGPT showed an ad from Inspirato.
Text ad: “Discover a Better Way to Vacation”
Price question · Oct 3, 22:58 ET
In a conversation that began “is airbnb luxe worth the price”, after the follow-up message, ChatGPT showed an ad from Vogo.
Text ad: “Find Airbnb Alternatives”
Worth it question · Oct 4, 02:44 ET
In a conversation that began “we're two retired couples who want a villa in tuscany for two weeks next september, which booking sites are trustworthy for that?”, after the follow-up message, ChatGPT showed an ad from SopranoVillas.
Text ad: “Find Your Luxury Villa in Tuscany”
Long scenario question · Oct 4, 01:54 ET
In a conversation that began “airbnb service fee percentage”, after the follow-up message, ChatGPT showed an ad from Jotform.
Text ad: “Airbnb Check-In / Check-Out Policies Form”
Price question · Oct 4, 04:51 ET
In a conversation that began “homes and villas by marriott vs plum guide for a luxury rental in london”, after the follow-up message, ChatGPT showed an ad from Flairova.
Text ad: “Preview Member Rates”
Comparison question · Oct 4, 04:11 ET
Question types
How the conversations on this topic were asked, and how many of the shown ads came from each kind.
| Question type | Ads shown | Share |
|---|---|---|
| Best for | 31 | 20.1% |
| Fix or choose | 24 | 15.6% |
| Long scenario | 24 | 15.6% |
| Comparison | 21 | 13.6% |
| Price | 22 | 14.3% |
| Short search | 16 | 10.4% |
| Worth it | 16 | 10.4% |
More in Travel & Hospitality
Other Travel & Hospitality topics (ads shown):
How this data was captured
We used logged-out ChatGPT from US internet connections and started a new conversation for every question. Message 1 was the question. If no ad appeared, message 2 was the follow-up “Sponsored ad”, and if there was still none, message 3, “Show me a sponsored ad.”, was a last try. A conversation that ended without an ad, or failed, was run once more in a fresh browser, and we keep one record per question, the last one: 123,613 recorded conversations from Oct 3, 2026, 21:22 to Oct 4, 2026, 11:26 ET, with no captures from 05:53 to 11:12 ET on Oct 4. Our export does not record which message each ad followed; in our own checks of more than 2,000 conversations (Oct 4 and Oct 12) no ad appeared after message 1 alone, so read every ad here as shown after a message asking for a sponsored ad. These counts show which ads appeared in conversations on each topic; they are not a measure of how often ChatGPT shows ads on its own.
Only ads drawn on screen count as shown. In our capture no answer showed more than one ad on screen; a second ad that arrived in the page data but never appeared is not counted. Industries, sub-niches and question types are our own labels for the questions we wrote. Independent; not affiliated with OpenAI. Full methodWhy this is not an ad rateWhat the ads looked like
How does your brand show up in ChatGPT and AI search?
We look at the answers and ads shown for your category and where your brand appears in them.