How should I waitlist a single day in an otherwise open week?

[MicheyMouse]

Day 1 is available. Day 2 is not available. Day 3-7 is available.

What is the safest way to waitlist with the highest possibility of being successful?

 

[atthebeachclub]

I’d book the available days and waitlist the one day, then combine when you hopefully get that last day.

 

[Simba's Mom]

I’d book the available days and waitlist the one day, then combine when you hopefully get that last day.

But what if you don't? Would it be safer to book days 3-7, and waitlist for 1-2. That would be my plan, since I'm so afraid I'd end up having to check out, then check back in.

 

[atthebeachclub]

But what if you don't? Would it be safer to book days 3-7, and waitlist for 1-2. That would be my plan, since I'm so afraid I'd end up having to check out, then check back in.

I’d probably adjust my vacation dates it if didn’t work out, or book another room category as backup just in case. This is where having extra points is helpful.

 

[CarolynFH]

But what if you don't? Would it be safer to book days 3-7, and waitlist for 1-2. That would be my plan, since I'm so afraid I'd end up having to check out, then check back in.

I'd book day 1 and days 3-7 to be sure I have them, then WL day 2 because a single night is more likely to fill than 2 nights. But I'd book a backup reservation somewhere, just in case the WL didn't fill. I wouldn't like having to move twice if the WL didn't fill, but I'd like it even less if I didn't get days 1 & 2 at all.

 

[muppets3d]

What I'd probably do is book days 1&2 at a different resort if available and waitlist days 1&2 at my preferred resort. Yes I know that a two day waitlist isn't as likely to come through but I'd rather have something even if it means having to move. I would not want to move twice, which is the alternative if my waitlist for day 2 only does not come through.