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Vacation rentals in Galena

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Top-rated vacation rentals in Galena

Guests agree: these stays are highly rated for location, cleanliness, and more.

Romantic Stone Cottage Retreat
SUPERHOST
Entire house · 2 guests · 1 bed · 1 bath

Romantic Stone Cottage RetreatThe Bawden Furnace Schoolhouse was built in the 1870's and is close to downtown Galena (3.2 mi.), art and culture. The rustic ambiance, natural surroundings, and airy floor plan with wood burning stove make it easy to relax, unplug and unwind. The schoolhouse is perfect for couples and solo adventurers who are looking for a true getaway.

Dawson's Remise Luxury Accommodation
SUPERHOST
Entire apartment · 2 guests · 1 bed · 1 bath

Dawson's Remise Luxury AccommodationEnjoy a luxurious stay in our remise ("carriage house"), complete with authentic Art Deco and Industrial furniture and design. We took great care in ensuring top notch craftsmanship and amenities, so as to create an inviting environment that you won't want to leave! Hidden away off the quaint and historic Park Avenue, you'll enjoy a quiet and restful stay whilst within walking distance to Main Street Galena and all it has to offer.

Beautiful Miner's Cottage in a Garden
SUPERHOST
Entire house · 2 guests · 2 beds · 1 bath

Beautiful Miner's Cottage in a GardenThis 1840's miner's cottage in the heart of Galena is only 3 blocks from beautiful, historic and fun Downtown Galena Main Street, but is far enough to have quiet times in the quarter acre yard of perennial gardens as well the expansive 2 story front porch, and 3rd porch off the kitchen, with gas grill. The house sits on a corner lot in the Galena National Historic District. The bathroom and kitchen are newly remodeled and the entire house is designer decorated. Beautiful!

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Popular amenities for Galena vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Galena

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  1. Entire apartment
  2. Dubuque
Canary Hill Cottage
$86 per night
SUPERHOST
  1. Entire apartment
  2. Galena
Apt#2 On Main St w/breakfast & parking
$196 per night
SUPERHOST
  1. Entire apartment
  2. Galena
Ulysses Suites, Suite 202
$214 per night
SUPERHOST
  1. Entire house
  2. East Dubuque
A MUST SEE! Entire Lake House & Garage. Amazing!
$182 per night
SUPERHOST
  1. Tiny house
  2. Bellevue
The Shady Haven
$139 per night
SUPERHOST
  1. Tiny house
  2. La Motte
Off-grid Tiny House farm stay
$62 per night
SUPERHOST
  1. Entire apartment
  2. Galena
Fireplace Apartment on Main Street Galena
$109 per night
  1. Entire townhouse
  2. Galena
Cozy townhome in the heart of The Galena Territory
$127 per night
SUPERHOST
  1. Camper/RV
  2. Bellevue
Riverfront Bunk Camper
$68 per night
SUPERHOST
  1. Entire house
  2. East Dubuque
Cozy Oasis/DBQ-Galena Locale-Pets/Outdoor Patio
$82 per night
SUPERHOST
  1. Entire cabin
  2. Bellevue
Mississippi River Cabin
$142 per night
SUPERHOST
  1. Entire house
  2. Galena
Newly Renovated. Gorgeous Retreat!
$156 per night

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 book a Galena vacation rental?

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.

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