First of all, remember that when websites like Groupon post deals, most are for within the next few months. So now, you can get deals for October-December pretty cheap. Secondly, now is a time when many aren't thinking about vacations so it can be a wise time to buy!
A couple tips to remember: When thinking about purchasing a vacation Groupon, do a few things.
1. Look up the resort on Trip Advisor. Trip Advisor is one of my favorite sites and I use it for every trip, yes every trip! It provides great reviews and real pictures of the resort. Like any travel review, you have to sort through and decide what is improtant to you. I reccomend reading at least 10 reviews. Some people (and we all know the type) just don't travel well or are extra picky, so you need to figure out the facts of any review. I always looks at the pictures and look for key items such as what ten people said about the rooms, food, and staff.
2. Call the resort first and see if they have availability for the time you want to go. They may only allow a certain number of groupon per week for example. Ask questions and make a decision on if it is worth it to buy the Groupon. Hopefully you have already read the blackout dates and fine print!
3. Buy that vacation with one of your reward credit cards or airline cards! Might as well get some miles or points or cash back!
Airfare: Have you check your air miles lately? See if you have enough miles to travel or get a discount. many airlines offer fall discounts for trips! I have been researching vacations and we can travel to place like Mexico, Hawaii, or the Carribbean all for anywhere between 30-60,000 miles and thats from Seattle! If you don't have enough miles, see if you have enough to get to a close airport or port of call. Cities like Dallas, Miami, Washington, Chicago, or New York. Cities like these have non stop flights to paradise and can be cost effective.
Also: When searching for airfare using miles, it is my direct expierience that the offers and miles change by the minute! So get an idea of where you can go, pick out a resort (but don't buy yet), then secure your flight. What cost 30k miles last week, might come up 60k today, and might be back to 30k on Monday! Its a brutal game these airlines play with us so be strong and win!