Galena is renowned in the travel world as one of the best day trips out of Chicago.
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That being said, a longer stay in Galena is never a bad idea. The small town is famous for its cozy, community-driven vibes. Slow living meets charm and innovation, as Galena is home to historic architecture along with plenty of trendy contemporary projects, from fine dining to hospitality.
Unsurprisingly, Galena is at its most charming when September and October roll around. Trees change colors, creating scenic views in the rolling hills that surround Galena. While the town’s walkable main drag is a treat any time of year, it feels like a Hollywood set when autumn arrives.
Whether you’re looking for a short weekend getaway or a longer fall escape, start with these Airbnbs in Galena, Illinois, for an enchanting stay. If you’re big on historic stays, head to the bottom of the list. Galena has more than a few Airbnbs for rent that date back to the 1800s—including a presidential home.
[This article is part of TravelAwaits’ new Airbnb and Vrbo recommendation series. We dig into listings to identify the crème de la crème of Guest Favorites, Superhost listings, and hidden gems, making it easy to find the perfect rental for your next trip.]
Best Airbnbs in Galena, Illinois this autumn:
- Best for couples: Luxe Cottage
- Right on Main Street: Apt. #1A
- Top rustic stay: The Ranch
- Great for big groups: Galena RowHouse
- A budget-friendly pick: Skylight & Whirlpool Apartment
- Historic miner’s cottage with greenery: Miner’s Cottage
- Historic brew house: 1842 Bavarian Brew House
- Historic coach house: Corwith Coach House
- Historic presidential home: US Grant Guest House
Airbnbs in Galena, Illinois for a sneaky fall escape
Luxe Cottage
This one-bedroom cottage has room for four, but it’s perfect for a couple’s escape in Galena this autumn. The home is a short walk from Main Street, giving you a great location. But the backyard makes the home feel like its own oasis, fit with a hot tub where you can enjoy the fall breeze and changing leaves. There’s also an indoor gas fireplace for added cozy nights.
Apt. #1A
If you’d rather stay right on Main Street to maximize your time in town, this two-bedroom lets you stay in the heart of Galena. The building dates back to 1840 and is located above a popular restaurant, Cucina Bella. You’ve got two spacious bedrooms, plus a full kitchen, giving you the chance to handle basic meals while you enjoy Galena’s small-town charm.
The Ranch
Galena is primarily known as a picturesque small town with plenty of history—but you can find more country-style stays in the area. Welcome to The Ranch, a private suite located on a 37-acre ranch less than twenty minutes driving from Galena. The unit itself is secluded and has its own outdoor patio, hot tub, and outdoor kitchen. You can also find hiking trails on the grounds. It’s perfect for autumn-lovers who want to spend as much time outdoors as possible between adventures in Galena.
Galena RowHouse
If you’re visiting Galena with a large group, this rowhome can sleep up to ten guests thanks to its large five-bedroom layout. The rooms are well-sized and come with some perks, like the upstairs bedroom that has a freestanding tub. The home also has a lovely sunroom for afternoon coffees, along with plenty of historic features and antiques that are sure to catch your attention.
Skylight & Whirlpool Apartment
If you want a simple escape, look no further. This Galena Airbnb is located right on Main Street, giving you a great location. There’s also free parking on-site for added convenience. Though it’s a simple, shotgun-style apartment with a small bedroom, it’s ideal for couples who are in Galena for a short time to soak up the fall wonder.
Miner’s Cottage
Like the historic Airbnbs in Galena (listed below), this cottage dates back to the 1840s, when it was originally home to a miner. It’s located in the Galena National Historic District, but it’s got more than historic appeal. The home is surrounded by perennial gardens on a quarter-acre yard that’s particularly gorgeous during the fall season. There are also two porches where you can sip on your morning coffee without a care in the world.
1842 Bavarian Brew House
This large three-bedroom home dates back to the 1840s, at which time it served as a tavern. The home has been remodeled to maintain its historic wood features, then refurbished with modern finishes and furnished with upscale pieces. Even the original cellar has been remodeled to now include heated floors and a small gaming area. Out back, there’s a cozy sitting area. This is an exceptionally well-maintained historic home with room for six.
Corwith Coach House
This 1850s home was originally built as a stable for a local banker. It has since been painstakingly restored to maintain its many historic features while adding modern amenities, like the private furnished patio. But the real magic is inside. The home has a classic country design that’s elevated with high-end appliances and finished, giving you a perfectly polished stay despite its age.
US Grant Guest House
Did you know that one of the Airbnbs in Galena, Illinois was once home to a US president? Prior to serving as a general in the Civil War, Ulysses S. Grant lived in this home near downtown Galena. The three-bedroom home has since been tweaked to include modern features, but the rooms are full of historically accurate era pieces. In short, you’ll stay in a home that looks like it’s from Grant’s day and age, but feels like a contemporary stay thanks to its sneaky modern additions… like a running shower and TV.
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