AI Trip Planning: Find Vacation Rentals with Stays AI

You know the drill

Somebody says, "We should get away for a weekend this fall." Everyone agrees. And then it's on you.

So you open a booking site. Then another. Then Google Maps to check the drive. Then a group text with four links nobody clicks. An hour later you've got fourteen tabs open, a mild headache, and no plan.

Trip planning isn't hard because there aren't enough options. It's hard because there are way too many, and most of them look exactly the same.

That's the problem Stays AI was built to solve.

What Stays AI Is

Stays AI is the assistant built into Stays. You type what you're looking for in plain English, and it searches our directory and comes back with actual stays.

Here's what makes it different from asking a general-purpose chatbot to "find me a cabin":

It only knows stays that made the cut. Every property on Stays is reviewed and approved by a human before it's listed. So when Stays AI recommends something, it's pulling from a directory that's already been filtered for quality. It's the difference between asking the whole internet and asking a friend who's spent years collecting great places to stay.

It knows you. Your favorites, your Trips, the regions you follow, the Offers available to you, the Invites hosts have sent. It can work with all of it.

It doesn't make things up about listings. It answers from the real, structured details on each Listing Page: property type, amenities, vibe, location, rate range.

Start with a Real Question

Open the chat at stays.co/chat and pick the Traveler assistant. Then just ask, the way you'd ask a well-traveled friend.

The more specific you are, the better it gets. Compare these two:

• "Find me a cabin."
• "Find me a secluded cabin with a hot tub within three hours of Chicago that works for two couples."

The first one gets you a list. The second one gets you an answer.

A few prompts worth stealing:

• "Find cool stays within an hour of Grand Rapids, Michigan."
• "Pet-friendly A-frames with a hot tub in the Northeast."
• "What are some romantic, off-grid stays in the Pacific Northwest?"
• "I want a treehouse for my kid's birthday. What's out there?"
• "Show me lakefront stays in the Midwest that are good for a big family."

You can search by location, property type, vibe, amenities, and price range, in whatever combination makes sense for your trip.

Build a Shortlist as You Go

As Stays AI suggests stays, you can pin the ones that catch your eye. Pinned stays collect in your shortlist, and that shortlist follows you across every conversation.

This is where it starts feeling less like search and more like planning. Once you've pinned three or four places, try:

• "Compare my shortlist. What stands out about each one?"
• "Which of these is best for a group of six?"
• "Do any of these have Offers right now?"
• "Which two would work together for a road trip?"

Think of it like laying out your options on the kitchen table and having someone who's read every detail walk you through them. When you've narrowed it down, save the winners to your favorites or drop them into a Trip.

Ask About Deals

This is the part most people don't think to do.

Stays AI knows about current Offers from hosts and live Giveaways. So you can ask:

• "Any Offers from my favorites right now?"
• "Which Giveaways can I enter?"
• "Are there any deals on cabins in Michigan this month?"

Giveaways show up as cards you can enter right from the chat. Offers come with the host's instructions for redeeming them.

One honest note: if you're on the free plan, Stays AI may mention that Premium members saw a particular Offer sooner. It won't ever show you a deal before you're allowed to see it.

Let It Handle the Housekeeping

Stays AI can do more than answer questions. Inside the Stays app, it can take care of the little chores too, as long as you ask it to:

• "Add that one to my Fall Trip."
• "Favorite the first two."
• "Start following the Southwest."
• "Enter me in that Giveaway."

It only takes an action when you clearly ask for one. And if an action would let a host know who you are (like responding to a private Invite, which shares your first name with that host), it checks with you first.

What it will never do is buy anything. No memberships, no bookings, no purchases of any kind.

Already Use Claude or ChatGPT? Bring Stays with You.

If you already do your thinking in Claude or ChatGPT, you don't have to leave. You can connect Stays to either one and search the directory, check your favorites, and see Offers right inside the conversation you're already having.

So you could be planning an entire road trip in Claude (the route, the restaurants, the hikes) and ask it to pull real, curated stays from Stays along the way.

How the connection works:

• You add Stays as a connector and sign in with your own Stays account. The AI never sees your password.
• It's read-only by default. It can search and read, but it can't change anything.
• If you want, you can allow it to take actions for you, like saving favorites or entering Giveaways. It still can't make purchases.
• You can disconnect anytime and its access is gone immediately.

Setup steps for each one are here:

What Stays AI Can't Do (Yet)

We'd rather you know the limits up front than find them the hard way.

• It only searches Stays. That's the point, but it also means it won't find a property that isn't listed with us.
• It doesn't check live availability. Stays doesn't manage calendars. Once you've found a stay you love, click through to the host's booking options to see open dates.
• It doesn't quote final prices. It can tell you a stay's typical rate range. The exact price for your dates lives on the booking platform.
• It's a first pass, not the final word. It's very good at narrowing a big field down to a handful. The last call, the one that comes down to taste, is still yours.

A Simple Way to Try It

Next time someone says "we should get away," skip the fourteen tabs. Open Stays AI and type one honest sentence about the trip you actually want:

"Two couples, a long weekend in October, somewhere quiet with a fire pit, no more than four hours from Detroit."

Pin what you like. Ask it to compare. Check for Offers. Then send the group text with two great options instead of twelve mediocre ones.

That's a plan. And it took you ten minutes.

Keep Reading

• How Travelers Can Get the Most Out of Stays
• Is Stays Premium Worth It?
• Stays vs Airbnb: Different Tools for Different Purposes