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I’m curious to know how you all handle calendar gaps.
As an example, here’s something I recently tried.
Aug 28 - Sep 1 (Sun night - Fri) were open in my calendar. On the 21st, I dropped my price by $5 each day. It’s now the 29th, and I’ve dropped the price by a total of $45/night. This block of dates is still unbooked.
I’m curious, what strategies do you all use to book unbooked, near-future date blocks?
It’s up to the market. If no one wants to stay, no price change will make a significant difference. I cut prices for last weekend, I then had a booking. Was the price the reason, I don’t know! There were very few places left unbooked in my area.
If you don’t have to many properties to manage I think it’s just better to make a search to see the price of other similar properties in your area, and adjust your price accordingly.
I used to drop my prices if we weren’t booked a week out. I realized that I was feeling resentful of guests who were getting everything I offer at such a low price so I stopped lowering the price. I figured I’d prefer a day off to an underpaying guest. We’ve been pretty fully booked at our regular price.
Underpricing the competition always works for me too! It’s not ideal, but for me it’s better than nothing at all.
I think that under-pricing the competition may get asses in seats for the short term, but in the long term you are harming yourself. If everyone lowers their prices there will come a time when we are losing money by hosting.
I’m not too worried about that. I’m very confident that both capitalism and greedy hosts like myself will do their job. 
I had today and tomorrow that was free but I was last available in the city.
I got this morning a booking for a price (one person) 650 dollars for two days.
So it’s always a question of demand/offer.
Is this higher, lower or your normal pricing?
I don’t have the same price every day.
But basically my lowest price can be 80-90 dollars a night with a normal price 130-140 dollars so it’s much higher.
For last minute availability I prefer certainty over profit maximization, so I’d rather cut my price by $20-30 a night and get a 2-3 night booking rather than risk having the place empty for a long stretch, or having to resort to consecutive one night stays.
If OP had to cut his prices by $45 a night it sounds like he was overpriced quite a bit for that particular time period.
I’m not booked every night and don’t want to be. Occasionally I raise my price on an open night and I’m usually disappointed when it gets booked (which is more often than not). The problem with price manipulation is that you have no idea what the demand is. And it’s hard to ask us as we may have a different kind of listing, price point, attractions and so on.
Then you’re not raising the price high enough. Factor in a nice meal at a posh restaurant into the price, and if it does get booked, you’ve got a nice evening out to look forward to
Ha! It’s not that kind of place. I’m able to raise the price enough to buy a nice beer at a posh restaurant.
We average $110 but depending on time of year can be from $99 to $150. Have just gone pet friendly and have more bookings. We have two dogs, a cat and birds, no longer chooks.
It is interesting to have to put a value on your time like you do with Airbnb hosting. With a regular job you never have the choice to work or not on a given day, but when you have the freedom to set your own rates it really puts into focus what you value!
I’m being very aggressive this summer so I can relax in the winter when rates are 1/3 what they are now. I haven’t had an unbooked day since May 15 so I’m starting to look forward to a slowdown! I thought tonight was going to break my streak, but instead I’ll be treating myself to something nice. 
That’s how my dog boarding business is. There are times when I have too many dogs, but I have to take them when people are vacationing, not when it’s convenient for me. Winter is a great time to enjoy good food and drink, or shows, or museums or travel…
That is true, my problem guests were the result of me dropping rate to fill empty weekend.
By how much do you drop your price to get last minute-bookings?
Like you, I prefer a booking to no booking. I found that if I set my prices to Airbnb’s suggested tips a few days beforehand I’ll book those nights for the most part.
But I’m now thinking I can set the price to Airbnb’s tips + X%, I’ll still get the bookings plus more money.
I’m working to try and calibrate X.
Have you found that being pet-friendly to cause more wear and tear on your property? Did you charge more or set specific rules as a result?