Chesterfield Vacations from $530

You can snap up a vacation package to this popular destination from $530 on Expedia. However, how much your vacation to Chesterfield costs will depend on the length of stay, hotel choice and season.

If you’re looking to snag a cheap Chesterfield vacation package, consider visiting in February, November and December. You’ll generally find better rates on airfares and hotels during these months — perfect for a budget-friendly getaway.

Usually, a handful of days is enough to tick off the main attractions during your Chesterfield vacation. But if you want to have time to unwind or go on day trips, consider extending your itinerary.

From attractions such as Castlewood and Magnolia Grange to its terrific history, a Chesterfield vacation is sure to exceed your expectations. With so much to see and do, it’s time to find out for yourself why Chesterfield is such a good vacation destination.

Begin your search for a Chesterfield package deal by entering your destination and preferred trip dates under our “Packages” tab. Then apply a few filters, like “Property type” and “Popular locations,” to tailor the results to your exact needs. You can also sort by “Package discount” and discover offers that come with unbeatable savings. If you don’t find the perfect Chesterfield package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chesterfield getaway off to a flying start.

An Expedia vacation package could land you great savings when compared to booking flights and stays individually. Better still, you can tailor your Chesterfield getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Secure incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Chesterfield vacation.

If you’re anything like us, you love traveling the world but are not a fan of the price tag that can come with it. That’s why we’ve created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Chesterfield break across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.