Galena vacation rentals

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Top-rated vacation rentals in Galena

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The Brick Apartment above Main Street Galena

My apartment is located right on Galena's historic main street also known as the Helluvahalfmile. There are great views, restaurants and dining, family-friendly activities, and nightlife. You’ll love my place because of it's location, the ambiance, people and the Galena main street life. You are right above my restaurant, which serves coffee, breakfast and lunch!

$111 per night
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Rustic Apartment overlooking Franklin & Main St

Hey there! We exposed the old original brick and hard wood floors inside. We installed an electric fireplace with a big comfy couch right in front of it. We do have cable TV with a variety of channels for you. There is a kitchen complete with an oven, stove, microwave and fridge if you are going to channel your inner chef. The bathroom has a shower and tub, and a built-in bathroom heater to keep it warm for you! This apt is above a coffee shop!

$111 per night
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The Loft Apartment on Main Street Galena

Hey there! This apartment was completely renovated and we exposed the old original brick and hard wood floors inside. There is comfy couch right waiting for you! We do have cable TV with a variety of channels for you. There is a kitchen complete with an oven, stove, microwave, fridge & dishwasher. If you are going to try out your chef skills, the kitchen is big enough for two! The bathroom has a shower and tub, and a double vanity for the both of you! This apt is above a coffee shop!

$113 per night

Vacation rentals for every style

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Galena house rentals

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The Owl House, a charming home near Main St.
$310 per night
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Beautiful Miner's Cottage in a Garden
$128 per night
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Romantic Stone Cottage Retreat
$155 per night
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1842 Bavarian Brew House
$184 per night
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401 Madison - Modern Historic Luxury Escape
$176 per night
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Upscale Resort Getaway 5 Kings Hot Tub Firepit
$590 per night
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Galena RowHouse - Downtown with parking included!
$273 per night
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NEW! 'The FiveTen Federal' - Downtown Galena Gem!
$297 per night
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Driftless Get Away
$139 per night
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Historic Downtown 1852 Home - Newly Renovated
$500 per night
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Getaway Galena Home walking distance to downtown
$212 per night
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Farmhouse Retreat
$147 per night

Galena condo rentals

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Cozy Condo w/Amazing LAKE VIEWS, screened porch
$166 per night
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Chic 2bd-Cozy Wooded View-Easy golf course access
$179 per night
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Lake Point Hideaway
$133 per night
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Elle & Becks Second Floor Suite
$489 per night
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Lake Front Getaway
$260 per night
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Galena, IL, Studio #2
$151 per night
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5★ Condo~NO CLEAN FEE~Jacuzzi~INDOOR POOL~Balcony
$211 per night
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Galena, IL, 2 Bedroom #1
$195 per night
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Galena, IL, 1 Bedroom #1
$164 per night
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Studio @ Wyndham Galena * Fireplace* Beautiful*
$129 per night
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Studio condo in galena, IL.
$232 per night
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Galena, IL, 1 Bedroom S #1
$164 per night

Your guide to Galena

Welcome to Galena

With a history as rich as the mineral deposits for which it’s named, Galena is a charming small-town getaway in the heart of the Midwest and the county seat of Jo Daviess County. Though it seems unimaginable now, Galena once rivaled Chicago in population. Back in the late 1820s, thousands flocked here to mine its namesake ore, which had long been used by Native Americans for burial rituals and trading. Even an American president has called Galena home: Ulysses S. Grant’s mansion, presented to him by the townspeople in the 1860s, is one of the town’s most popular tourist destinations. Many Chicagoans call Galena their second home. Galena’s main street, sometimes called the Helluva Half Mile (riffing on Chicago’s Magnificent Mile), is lined with Victorian-era storefronts and eateries. The rolling hills along the horizon draw visitors for skiing in the winter and hot-air ballooning during the warmer months.


How do I get around Galena?

Galena is equidistant from the major Midwestern hubs of Chicago and Milwaukee, each of which is a little less than a 3-hour drive away. Given the town’s small footprint, Galena isn’t served by public transportation, so having a car is a must for getting there and around. Walking around downtown Galena — including the charming half-mile Main Street — is a great way to get a feel for the area, but car travel is necessary to reach destinations beyond the town’s core. There aren’t many taxis in Galena, though a handful of rideshare options may be available in a pinch.


When is the best time to stay in a vacation rental in Galena?

Galena rolls with the Midwestern weather patterns, which is good news for visitors. Perhaps the most beautiful times of year to visit are late spring, when the surrounding hills are in bloom, or autumn, during leaf-peeping season. Summertime in Galena is marked with outdoor bistro seating on Main Street, live music and festivals on the weekends, and strolling families wielding ice cream cones. Though winter is a little quieter (and can be quite cold), it has its own draws. Area resorts tucked into the hills host downhill skiers and snowboarders, and cross-country ski trails criss-cross through nearby nature preserves and Apple River Canyon State Park.


What are the top things to do in Galena?

Great Galena Balloon Race

One of Galena’s best-known tourist attractions is also one of its most magnificent. Every third full weekend in June, weather pending, thousands come to marvel at a series of colorful balloon races across the prairie. The pros race at dusk on Friday night and at dawn on Saturday and Sunday. Meanwhile, amateurs can enjoy leisurely hot-air balloon rides with on-site rental companies.

Galena Grant Park

Toward the south end of bustling Main Street, a pedestrian bridge stretches across Galena River to this stately Victorian-era park. True to the period design, the park’s paths lead under decorative arbors to the town’s Civil War monument and gazebo, and the formal fountain stands out as a landmark.

West Street Sculpture Park

On the funkier side of Galena’s tourist attractions is this 2-acre park featuring metal sculptures of various scales. Ranging from rusted-out can contraptions to impressive postmodern art statements, the dozens of sculptures here are spread all over the park (including some in its trees), exposed to the elements, and open to visitors year round.