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Galena vacation rentals

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Top-rated vacation rentals in Galena

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

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SUPERHOST
Entire loft · Galena
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!
$116 per night
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SUPERHOST
Entire rental unit · Galena
Shiplap Apartment on Main
This 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!
$116 per night
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SUPERHOST
Entire cabin · Galena
New! Beautiful 3bdrm/3bth cabin, hot tub, kid/pets
Welcome to Galena Haven! Beautiful custom decor throughout the house, and lots of luxuries! Newly designed gorgeous cabin décor. Enjoy a private hot tub on the back downstairs patio. Relax by indoor fireplace, or have a nice outdoor fire at the fire pit. Surrounded by 2 acres for privacy, especially in the back with woods. Lots of fun activities, home fully stocked! 3 bedroom/3 bath home. Ms. Pacman, pingpong/air hockey, snow cone, popcorn, cotton candy machine! Community pool, lake, stables.
$254 per night

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Stay near Galena's top sights

Photo of Blaum Bros. Distilling Co.
Blaum Bros. Distilling Co.14 locals recommend
Photo of US Grant Home Historic Site
US Grant Home Historic Site12 locals recommend
Photo of Grant Park
Grant Park7 locals recommend
Photo of P.T. Murphy Magic Theatre
P.T. Murphy Magic Theatre7 locals recommend
Photo of Dowling House
Dowling House4 locals recommend
Photo of Old Blacksmith Shop
Old Blacksmith Shop4 locals recommend

Galena house rentals

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SUPERHOST
Entire home · Galena
Romantic Stone Cottage Retreat
$165 per night
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Entire home · Galena
Renovated Historic Gem in Downtown Galena
$200 per night
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Entire home · Galena
New! Historic Galena Home close to Main Street.
$159 per night
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SUPERHOST
Entire home · Galena
Beautiful Miner's Cottage in a Garden
$148 per night
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SUPERHOST
Entire home · Galena
Beautiful Private Wooded Lot, Fireplace, Whirlpool
$209 per night
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SUPERHOST
Entire home · Galena
The Owl House, a charming home near Main St.
$311 per night
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Entire home · Galena
NEWLY Renovated, Amazing Views, Hot Tub, Game Room
$414 per night
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SUPERHOST
Entire home · Galena
1842 Bavarian Brew House
$184 per night
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SUPERHOST
Entire home · Galena
Spectacular Lodge in Galena Territory
$330 per night
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SUPERHOST
Entire home · Galena
Black Hawk Hideaway
$276 per night
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SUPERHOST
Entire home · Galena
Charming fairy-tale cottage for a relaxing getaway
$180 per night
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SUPERHOST
Entire home · Galena
Stagecoach Valley Getaway
$264 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.


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 book one of the area’s vacation rentals 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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  5. Galena