Two hours west of Chicago, the small river town of Galena turns into prime autumn territory each September and October, when the hills around it change colour and its walkable Main Street starts to resemble a film set. The town is best known as a day trip from the city, but a longer stay is where it shines — and with a stock of 19th-century buildings, there are plenty of rentals with genuine history attached.

For couples, a one-bedroom Luxe Cottage a short walk from Main Street offers a hot tub in the backyard and an indoor gas fireplace. Staying right in the action? Apt. #1A sits above the restaurant Cucina Bella in a building dating to 1840, with two bedrooms and a full kitchen. On a budget, the Skylight & Whirlpool Apartment is a simple shotgun-style spot, also on Main Street, with free parking.

Bigger crews are covered too: the five-bedroom Galena RowHouse sleeps ten and comes with a sunroom, antiques and a freestanding tub in the upstairs bedroom. If you'd rather swap town for countryside, The Ranch is a secluded private suite on 37 working acres about 20 minutes' drive from Galena, with its own patio, hot tub, outdoor kitchen and hiking trails.

The history buffs get the good stuff. A Miner's Cottage from the 1840s sits in the Galena National Historic District on a quarter-acre of perennial gardens with two porches. The 1842 Bavarian Brew House was once a tavern; it's been remodelled with original wood features, and the old cellar now has heated floors and a small games area — sleeping six across three bedrooms. The Corwith Coach House, an 1850s former stable for a local banker, has been restored with high-end appliances and a private furnished patio.

Then there's the showstopper: the US Grant Guest House, a three-bedroom home where Ulysses S. Grant lived before his Civil War command. The rooms are furnished with era-appropriate pieces, but modern touches like a proper shower and TV mean you're camping out in history without actually roughing it.

Galena works for a weekend or a full week away — walkable downtown, restaurants and wine bars within a few blocks, and rolling countryside on the doorstep. It suits couples chasing a cozy autumn break, friend groups wanting a house with character, and anyone who likes their accommodation to come with a story.