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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.

Farmhouse Style Apt, Steps from Main St, Parking!
Entire rental unit · 4 guests · 2 beds · 1 bath
Farmhouse Style Apt, Steps from Main St, Parking!Nestled in the heart of historical downtown Galena, our quiet and private apartment suite is only steps away from shopping, dining, entertainment and everything Galena has to offer. Wake up to a full tea and coffee bar and make yourself at home as you wind down at the end of the day. As you walk out and down the stone stairway, you will find yourself in the middle of Main Street! A reserved, off street, parking space is included with your stay! We fully clean and disinfect between stays.
The Brick Apartment above Main Street Galena
SUPERHOST
Entire loft · 2 guests · 1 bed · 1 bath
The Brick Apartment above Main Street GalenaMy 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!
Shiplap Apartment on Main
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bath
Shiplap Apartment on MainThis apartment Is located at 303 N. Main street, to the back of the building. You have coffee shops, breakfast, lunch and dinner places located all within a 1/4 and bars to finish off your night. It has just been newly renovated to expose the old brick in the building along with the original wood floors. You will be above a coffee shop, with freshly roasted coffee waiting for you in the morning!

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Other great vacation rentals in Galena

SUPERHOST
  1. Entire residential home
  2. Galena
Beautiful Miner's Cottage in a Garden
$92 per night
SUPERHOST
  1. Entire rental unit
  2. Galena
The #2 at Cathouse Suites, Dogs OK w/$$
$76 per night
  1. Entire rental unit
  2. Galena
Private Apartment Suite on Main St with parking!
$88 per night
SUPERHOST
  1. Entire rental unit
  2. Galena
Dawson's Remise Luxury Accommodation
$115 per night
  1. Entire rental unit
  2. Galena
Quiet 2 Bedroom, Main Street, Parking! Sleeps 4-5
$112 per night
SUPERHOST
  1. Entire rental unit
  2. Galena
Gameroom in Galena
$149 per night
SUPERHOST
  1. Entire rental unit
  2. Galena
Downtown Gem for Two
$136 per night
SUPERHOST
  1. Private room
  2. Galena
The Ranch, a social distination.
$159 per night
SUPERHOST
  1. Entire rental unit
  2. Galena
Ulysses Suites, Suite 202
$204 per night
SUPERHOST
  1. Entire guesthouse
  2. Galena
The Guest House - Private and All Yours
$105 per night
SUPERHOST
  1. Entire residential home
  2. Galena
The Owl House, a charming home near Main St.
$276 per night
SUPERHOST
  1. Entire residential home
  2. Galena
Romantic Stone Cottage Retreat
$155 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.