I'm trying to book a vacation that will have 3 different destinations (all three require flights). It will be 14 days total, but it can start basically any day in September and the amount of time in each place can't be changed. Is there any EASY way to check the best set of days to do this trip, flightwise as well as making sure Airbnbs or hotels are available at all 3 locations during that timeframe? I normally use Kayak for trip planning, but I can't think of a simple way to do this one on Kayak, even with multi city.

Just curious what destination?

I prefer Google flights over Kayak, personally. If it were me, I would focus on 2 or 3 hotels in each place, then play around with the dates. I dont think the sites have level of detail of planning.

Generally I look at flights on Google, then look at hotel options.

I would not book flights anywhere but direct (google does take too to the direct website).

Depending what you are doing, one way flights on different airlines may be beneficial.

Sounds like a job for a travel agent.

Since the requirements are based around the length of stay in each place, I would start with searching the hotels for availability.
Once you know when/where you are staying, search for flights.

What is the criteria for declaring 'best set of days'?

I like using flightconnections.com and Google Flights for planning.

07ag said:

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What is the criteria for declaring 'best set of days'?

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Cheapest, and best selection of Airbnbs available during that time period.

• Is your budget driven by flight cost or lodging cost?
• What are the three cities?
• What are the durations in each city?
• Do you care about connecting flights vs nonstops?

3 cities doesn't sound that difficult. I can tell you from experience that 6 cities is where most travel agent booking software and fare specials fall apart. Especially if you're not going RTW.

You lost me at Airbnbs

Where are you planning to go ?

with the info offered so far, start an excel spreadsheet to gather info. Flightconnections to find routes. Google flights to research prices for individual flights. Another column for number or airbnbs available, then make a decision

Good luck!

I would feed your options, preferences, budget, etc into ChatGPT. It will give you a good starting point.

Yeah, the best way to do this is just to start a spreadsheet. There's tools out there for flights and hotels individually but otherwise it will just take some legwork. Personally I usually start with the longest/most expensive flight and look for a deal, then work down from there. I always get flights and then fill in hotels unless there is an extremely specific hotel I want to stay at that has limited availability. Usually hotels are a lot easier to find than flights unless there is a major event in the city you're going to.