We keep a binder with spreadsheets to record all of the dates we were booked. At the end of each season, we do a full tally of them by weekdays and weekends, as well as holidays, and total them up. At the end of each year, we do the same. After awhile, it's really useful at gauging when guests are most likely to book, and how much to discount for longer stays.
What those numbers look like, and what kind of discount you give is going to depend entirely on what type of rental you have, where it's located, and what kind of guests you typically get (vacationers, snowbirds, students, business folks).
More importantly, factor in what expenses longer term stays accrue- is there a higher cleaning bill? A longer period before you can rebook once they leave, bc of the cleaning? Do you provide any amenities like wifi that has a data cap, long distance phone calls from a landline, that might be used more heavily than with short term guests? A cord of wood for firepits that gets used more? Supplies? Laundering? Replacements of things from heavy use? Likewise, are there any fiscal benefits of long term bookings? Would you have lost more money by only booking short stays, since weekdays are less common? Do you have any amenities that you charge for? We have a wine rack that guests can enjoy for a $10-20 donation, based on the type. I also make a lot of handmade soaps, balms, lotions, and curated loose teas, that I usually sell at our local farmers market, but I provide guests with free ones, and additional ones at retail price on request- it's been extremely lucrative, bc most guests end up asking and buying some to use or take home. I also keep a stock of basic stuff guests might forget. like ibuprofen, asprin, shampoo and conditioner, coffees, etc- i have a freebie stash policy for one offs, and unopened ones for purchase. If you buy those in bulk, and just charge an extra dollar or two for guests, long term stayers tend to buy a lot, bc it's more convenient than running around and finding a store in a strange town. Stuff like that can help you make up for a discount, profit wise.
Most important of all, can you justify the expenses of the discount while still making a profit? Heavy use will mean more repairs, replacements, and costs that cut into your bottom line. Charge what seems fair and justifiable, while still respecting your needs as a small business.
