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.

Guest favorite

Cabin in Durango

5.0 out of 5 average rating, 234 reviews

Cozy Cabin by the Pond

Quiet, private country location to relax and unwind. 9 miles west of Dubuque, close to Wineries, Heritage Trail, Sundown Mountain Resort. Cozy cabin and quarter acre pond. Sun yourself on the patio, or nap in the shade of the covered porch. We're sure you will love this space as much as we do. Not suitable for children under 12, we strictly enforce no children and no pets. Outdoor relaxing space, gas grill. Fully stocked cabin, with the essentials such as coffee, tea, spices and condiments.

Oct 15 – 22

G$30,585 GYD per night
Guest favorite

Apartment in Galena

4.83 out of 5 average rating, 454 reviews

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.

May 17 – 24

G$23,251 GYD per night
Guest favorite

Apartment in Galena

4.94 out of 5 average rating, 296 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.

Sep 6 – 13

G$29,318 GYD per night

Popular amenities for Galena vacation rentals

Stay near Galena's top sights

Grant Park11 locals recommend
Blaum Bros. Distilling Co.28 locals recommend
Vinny Vanucchi's20 locals recommend
Durty Gurt's13 locals recommend
Fried Green Tomatoes49 locals recommend
DeSoto House Hotel7 locals recommend

Other great vacation rentals in Galena

Guest favorite

Home in Galena

4.96 out of 5 average rating, 137 reviews

1842 Bavarian Brew House

Nov 13 – 20

G$38,623 GYD per night
Guest favorite

Townhouse in Galena

4.94 out of 5 average rating, 103 reviews

Cozy villa with wooded views. Coffee bar included

Apr 7 – 14

G$30,321 GYD per night
Guest favorite

Home in Cuba City

4.95 out of 5 average rating, 187 reviews

Recharge your soul at “The Church”!

Mar 6 – 13

G$24,472 GYD per night
Guest favorite

Apartment in Galena

4.97 out of 5 average rating, 293 reviews

Apt#2 On Main St w/Reserved Parking

Jul 11 – 18

G$51,234 GYD per night
Guest favorite

Home in Galena

4.95 out of 5 average rating, 198 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

Oct 19 – 26

G$35,879 GYD per night
Guest favorite

Home in Dubuque

4.93 out of 5 average rating, 595 reviews

Mississippi River Views: Historic w/Modern Comfort

Aug 16 – 23

G$25,207 GYD per night
Guest favorite

Condo in Galena

4.99 out of 5 average rating, 190 reviews

Elle & Becks Second Floor Suite

Apr 15 – 22

G$89,897 GYD per night
Guest favorite

Cabin in Potosi

4.98 out of 5 average rating, 166 reviews

Unplug and get back to nature

Nov 17 – 24

G$29,096 GYD per night
Guest favorite

Apartment in Galena

4.94 out of 5 average rating, 376 reviews

Gameroom in Galena

Sep 5 – 12

G$38,878 GYD per night
Guest favorite

Cottage in Lena

4.95 out of 5 average rating, 155 reviews

Country Escape - Private Historic Schoolhouse!

Jun 8 – 15

G$25,574 GYD per night
Guest favorite

Home in Galena

4.93 out of 5 average rating, 134 reviews

Historic Downtown 1852 Home - Newly Renovated

Jul 23 – 30

G$119,473 GYD per night
Guest favorite

Apartment in Dubuque

4.92 out of 5 average rating, 110 reviews

1127 / Downtown Dubuque, first floor, free parking

May 11 – 18

G$17,188 GYD per night

Other great vacation rentals in Galena

Guest favorite

Home in Galena

4.99 out of 5 average rating, 78 reviews

King Bed Villa, Resort Amenities, Pools, Golf, Ski

Nov 3 – 10

G$34,678 GYD per night
Guest favorite

Cabin in Galena

5.0 out of 5 average rating, 27 reviews

Hot tub! In/Outdoor fires-Game Room-3 King beds!

Feb 15 – 22

G$140,152 GYD per night
Guest favorite

Home in Galena

5.0 out of 5 average rating, 17 reviews

Newly remodeled cottage! Pet Friendly!

Mar 20 – 27

G$31,913 GYD per night
Guest favorite

Home in Galena

4.97 out of 5 average rating, 78 reviews

Charming fairy-tale cottage for a relaxing getaway

Apr 11 – 18

G$36,724 GYD per night
Guest favorite

Cabin in Darlington

5.0 out of 5 average rating, 13 reviews

Hilltop Hideaway. Relax, unwind, and getaway!

Nov 15 – 22

G$21,682 GYD per night
Guest favorite

Cabin in Galena

4.97 out of 5 average rating, 30 reviews

Stunning 5 bedroom Cabin *Fantastic Location* l

Feb 21 – 28

G$129,750 GYD per night
Guest favorite

Apartment in Galena

4.91 out of 5 average rating, 70 reviews

Historic Downtown Galena Suite #7

Nov 14 – 21

G$22,938 GYD per night
Guest favorite

Cabin in Hanover

4.92 out of 5 average rating, 12 reviews

Sunset Ridge-Unique Riverview 1BD House by Galena

Sep 23 – 30

G$25,885 GYD per night
Guest favorite

Home in Galena

4.89 out of 5 average rating, 57 reviews

Driftless Get Away

Jan 13 – 20

G$30,742 GYD per night
Guest favorite

Home in Galena

5.0 out of 5 average rating, 38 reviews

cozy winter getaway! heated floors, sauna, hot tub

Dec 6 – 13

G$172,671 GYD per night
Guest favorite

Cabin in Hazel Green

5.0 out of 5 average rating, 91 reviews

Crooked Creek Cabin

Sep 13 – 20

G$36,425 GYD per night
Guest favorite

Townhouse in Galena

4.97 out of 5 average rating, 39 reviews

Galena Territory Retreat

Dec 1 – 8

G$38,569 GYD per night

Quick stats about vacation rentals in Galena

Total rentals

130 properties

Rentals with dedicated workspaces

50 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

50 properties are a good fit for families

Total number of reviews

17K reviews

Nightly prices starting at

G$10,469 GYD before taxes and fees

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.


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.


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.

Frequently Asked Questions

  • Are there pet-friendly house rentals in Galena?

    Four-legged friends are welcome in Galena. Choose from more than 10 house rentals for guests traveling with pets.

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

    Absolutely! We offer over 40 apartment rentals with self check-in in Galena. Enjoy a tailored experience with all the comforts you desire.

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

    Yes! Work meets play with ease at over 10 house rentals in Galena featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • 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 bed and breakfast rentals in Galena have wifi?

    Absolutely! We offer over 20 bed and breakfast rentals with wifi in Galena. Enjoy a tailored experience with all the comforts you desire.

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

    Experience the best of Galena with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly house rentals in Galena?

    Galena has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • 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 30 homes with wifi, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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