I like to look for free or cheap activities/events, combine that with free/cheap lodgings and then figure the rest out.
Helps that my fave vacation is hiking and tent camping.
What type of things do like to do? Are you active? Do u like to walk around small towns? Go to big cities? There are many ways to make even a normally-expensive vacation cheap.
For example, when I went to NYC, I took a cheap megabus to get there (I was nearby in DC), used points for a hotel, and mostly just wandered around checking out the free sightseeing (Central Park, State Island Ferry, etc). For food, we ate cheap and used various coupons. Happy hours also makes for great deals. I simply have a price point in my head what I am willing to spend on various things and chase the deals, ignoring everything else.
For more specific destinations, try coming up to Canada. Your dollar will stretch 30% more. There's Windsor, Stratford, Niagara, etc.
For example, in Windsor, you can tour the wine country. It's very inexpensive with many wineries offering free tastings. Hike to the southernmost point of mainland Canada (small entry fee). Tour the JP Wisers whisky distillery. Explore the historic towns of Walkerville and Amherstburg. So many summer festivals every weekend, many free.
A couple of years ago, my friend and I did a girls trip to Louisville. We stopped at the Keeneland track near Lexington (free to watch the jockeys train their horses) and skipped Kentucky Horse Park (pricey!). Then off to Buffalo Trace Distillery for a free tour and tasting. Wandered some small towns nearby. Then we moved to Louisville and spent a day at the Kentucky State Fair. For $10 each, we got a full day of entertainment. We also went for a walk across the state line nearby. I then got a Groupon to go trail riding near Louisville for $20ish per person. It ended up a cheap weekend.
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