Vacation rentals in Galena

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Top-rated vacation rentals in Galena

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Top guest favorite
A custom log cabin is framed by lush greenery and manicured landscaping. The warm wooden exterior features multiple gabled roofs and large windows. A stone pathway leads through the vibrant garden, creating an inviting approach to the entrance.
Cabin in The Galena Territory
4.96 out of 5 average rating, 112 reviews

Private, Galena Log Cabin

This custom log cabin is the perfect getaway for friends & family seeking the solitude of the Galena Territory and fine dining and shops just 10 minutes away on Galena's Main Street. Each of the 3-levels offers an owner's suite with bath. Cozy up to 2 fireplaces, grill on the deck, or make 'smores at the firepit. The cabin has high speed, fiber internet and the lower-level walkout features a 55” flat screen TV. Guests can access swimming pools & pool tables at the Owner's Club 7 minutes away.

Top guest favorite
An open living area features a light-colored sectional sofa paired with a rustic coffee table. A dining table with black chairs is visible, along with modern kitchen appliances and cabinetry. Natural light flows through large windows, enhancing the inviting atmosphere of the space.
Apartment in Galena
4.95 out of 5 average rating, 357 reviews

Downtown Gem for Two

Newly remodeled downtown apartment right in the middle of town. New furnishings, office nook with desk, full size kitchen and appliances, smart tv, free wifi, large open living space with private bedroom and bath. Very clean. Adjacent shared deck with table and chairs is available for use. This is a second floor apartment in the back of Simply Elegant Boutique so there are 17 steps to get to it from the outside. *Rest easy, every surface and door knob is disinfected after each stay.

Top guest favorite
The living area features mid-century modern furniture with vibrant green and orange chairs surrounding a coffee table. A gas fireplace is centered under a unique light fixture, and large windows allow views of the surrounding woods. A dining area is visible in the background.
Treehouse in The Galena Territory
4.98 out of 5 average rating, 184 reviews

Octagon treehouse Hottub-pool-fireplace-firepit

Unique "tree house" - an octagon tiny house, surrounded by the woods! 2 bedroom, 2 bathroom home you can enjoy the views of nature all around, with floor to ceiling windows. One king bed, one queen bed. Modern comforts with fun flash blacks. Private hot tub and firepit look into serene woods! Sit by the indoor gas fireplace and enjoy our record collection. Soak in a Japanese soaking tub. Enjoy fall colors or watch snow fall! Community indoor poor, seasonal outdoor pool, gym access

Top guest favorite
An open living space showcases exposed brick walls and dark wood flooring. A round wooden dining table with four chairs is positioned adjacent to a cozy black armchair and ottoman. The kitchen area includes a refrigerator and cabinets, with a warm light illuminating the room.
Loft in Galena
4.87 out of 5 average rating, 813 reviews

The Brick Apartment Main Street Galena

Hello! Welcome to our beautifully-renovated apartment, conveniently located on the north end of Galena’s historic Main Street. This unit is above Big Bill’s coffee shop, and boasts exposed original brick from the historic Logan House Hotel, hardwood floors, a kitchen (range, refrigerator, microwave, sink), and beautiful views of our historic town! Only feet from restaurants, shopping, and night life! Check out all our listings at Airbnb.com/p/galenaapartments ( copy & paste into URL)

Guest favorite
This historic brick home features multiple windows reflecting a classic architectural style. A stone garage, designed with modern doors, complements the house. Lush greenery surrounds the property, enhancing its natural appeal. A paved driveway leads to the garage, showcasing an inviting approach to the entrance.
Home in Galena
4.96 out of 5 average rating, 217 reviews

1842 Bavarian Brew House

Nestled in charming and historic Galena this beautiful home was built in 1842 by brewer Peter Specht from Bavaria. The cellar operated as his brewery and tavern while living in the home above. The house was extensively renovated in 2008. It remains full of character and charm, but now boasts an abundance of modern comforts. A quiet private patio and yard are the perfect spot for a morning coffee or a glass of wine. All within a few walkable blocks to Main Street, the heart of Galena!

Superhost
A charming cabin exterior is framed by a white picket fence adorned with colorful flowerbeds. The house features a sloped roof and warm wood siding, with lights illuminating the inviting entrance. Lush greenery surrounds the property, enhancing the tranquil outdoor setting.
Tiny home in The Galena Territory
4.94 out of 5 average rating, 163 reviews

Cozy Romantic Getaway*Fireplace on deck*King bed

Enjoy the cozy setting of this romantic nature retreat at The Hygge Haus. Hygge ("hooga") is about taking time away from the daily rush to be together with people you care about - or even yourself - to relax and enjoy life's quieter pleasures. Come hygge in our cozy house meant for two, wrap in a fuzzy blanket by a fire. Feel contentment in sharing a cozy meal at the table, talking on the chaise built for two. Relax, unwind, & explore the Galena Territory and nature. Cozy up!

Top guest favorite
The charming two-story miner's cottage features a welcoming front porch adorned with historic American flags. Lush greenery surrounds colorful flower beds, enhancing the outdoor space. The stone and white clapboard exterior reflects classic architectural elements within the Galena National Historic District.
Home in Galena
4.96 out of 5 average rating, 566 reviews

Beautiful Miner's Cottage in a Garden

This 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!

Top guest favorite
A modern living area features a cozy seating arrangement with two armchairs and a plush sofa. A decorative rug lies beneath a coffee table, while a television is mounted above a fireplace. Large windows provide natural light, complemented by artwork on the walls.
Apartment in Galena
5 out of 5 average rating, 138 reviews

Ulysses Suites, Suite 303

Ulysses Suites has just been completed inside the historic J. G. Schmohl building in the heart of downtown Galena, located at 213 to 217 S. Main Street. The location is walking distance to all the best restaurants and shops. We have 7 suites and a beautiful lobby that are modern and luxurious, with lots of historical character and texture as a nod to its previous existence as the Grant Hotel from 1895 to 1933. The Presidential Suite 303 is located on the 3rd floor.

Top guest favorite
A comfortable seating area features two black reclining chairs with plush pillows, set against a backdrop of exposed brick walls and modern lighting. A glimpse of the outdoor street is seen from nearby windows, enhancing the vibrant urban atmosphere.
Apartment in Galena
4.98 out of 5 average rating, 123 reviews

Suite Victory #4 On Main St w/Reserved Parking

Suite Victory #4- Beautifully renovated apartment on Main St. right where you want to be with Reserved Parking. Dining, entertainment, and shopping just outside your door. Open floor plan with beautiful views of downtown Main Street. King bed. Double sink vanity and large walk-in shower. Kitchen has island, quartz countertops, and new appliances. Stackable washer and dryer within the unit. Above Charlie’s Place Eatery on Main Street. MAX 2 PEOPLE. NO DOGS ALLOWED.

Top guest favorite
An expansive recreational area features warm wooden flooring and exposed brick walls. Comfortable seating arrangements include a sectional sofa and armchairs. A pool table is positioned center stage, with a wall-mounted television nearby. Large windows allow natural light to fill the space, creating an inviting ambiance.
Apartment in Galena
4.94 out of 5 average rating, 433 reviews

Gameroom in Galena

In the center of downtown Galena, we offer over 1500 sq ft. in a 1852 building. A bay window offers 180° view of Main St. A pool table, shuffleboard, pinball machine and bar are at your disposal. You'll have access to either Main Street from the front or Bench Street from the back. There is free parking on South Main Street and out the back on South Bench Street. There is no dedicated parking spot but parking opens up quit a bit in the evenings.

Top guest favorite
A welcoming living area features a comfortable sofa and a wooden coffee table. Large windows provide a scenic view of the landscape and river, allowing natural light to fill the space. A TV is mounted above a stone fireplace, creating a cozy atmosphere.
Home in Dubuque
5 out of 5 average rating, 180 reviews

Home by the River

Situated alongside the Mississippi River, wildlife abounds in every season. With eagles nesting nearby, there is always something new to see from the beautiful sunrises, cruise ships passing by, and watching the commerce of the barges and railroad right out the front window! This home has been recently refurbished and sits at the edge of our 15 acres. You can see us and visit with us if you like, or you can maintain privacy 10 acres away!

Top guest favorite
A decorative sign reading 'Dawson's Remise' is illuminated in warm tones, framed in black wood. Next to it is a textured pillow featuring a geometric red and black pattern, adding a modern touch to the setting.
Apartment in Galena
4.99 out of 5 average rating, 378 reviews

Dawson's Remise Luxury Accommodation

Enjoy 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.

Popular amenities for Galena vacation rentals

When is the best time to visit Galena?

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Avg. priceG$37,023 GYDG$36,605 GYDG$35,350 GYDG$34,932 GYDG$37,233 GYDG$39,115 GYDG$39,115 GYDG$38,278 GYDG$39,324 GYDG$40,579 GYDG$38,278 GYDG$38,278 GYD
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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Galena?

    Yes! Work meets play with ease at over 80 vacation rentals in Galena featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Galena?

    Four-legged friends are welcome in Galena. Choose from more than 40 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in house rentals in Galena?

    Experience the best of Galena with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Galena vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Galena, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Galena have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Galena. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Galena have self check-in?

    Absolutely! We offer over 10 house rentals with self check-in in Galena. Enjoy a tailored experience with all the comforts you desire.

  • Do boutique hotel rentals in Galena have a gym?

    Absolutely! We offer over 10 boutique hotel rentals with a gym in Galena. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Galena?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with self check-in, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

All about 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.

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.

Quick stats about vacation rentals in Galena

  • Total vacation rentals

    Explore 170 vacation rentals in Galena

  • Nightly prices starting at

    Galena vacation rentals start at G$8,367 GYD per night before taxes and fees

  • Verified guest reviews

    Over 17,990 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    170 of Galena vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Galena rentals

  • 4.9 Average rating

    Galena stays are highly rated by guests—averaging 4.9 out of 5!

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  2. United States
  3. Illinois
  4. Jo Daviess County
  5. Galena