
Vacation rentals in Galena
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Top-rated vacation rentals in Galena
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Popular amenities for Galena vacation rentals
Dog friendly vacation rentals in Galena

Johnson Apartment and Cathouse Suites, Dogs OK w/$ $
This was our first trip to Galena. Loved staying downtown where we could walk to coffee shops, restaurants, bars, and stores. The accommodations had a creative and whimsical vibe and were just as described, easy to access, and clean. Just what we were looking for.

Galena Getaway
Stayed here with family. Easy to find. Quiet. Layout worked out well. 3 bathrooms! Able to block off stairs. traveled with a senior dog with a bad knee. Kitchen had anything we needed. Relaxing after a day at Chesnut Mountain. Beds comfortable, bathrooms spotless. husband enjoyed the puzzle ball game. Nicely decorated to reflect the holiday season!

Historic Home with Pool Table and Dart Board
Jessica was very friendly. She gave upfront, easy instructions. The house was clean and easy to access. The description was perfect. We came for a weekend at UD. This house did not disappoint. Would definitely stay again!

Cozy Retreat | Hot Tub | Firepit | Dog-friendly
Family ski trip! It was perfect! 20min to Chestnut Ski resort and 15mins to downtown Galena! It was the perfect stay and plenty big enough. We will be back next year!

The Shady Haven (Tiny Home 1)
I've always wanted to stay in a tiny house and I couldn't have picked a better one to try. Loved the location, the cabin had everything I needed for a short stay, and Dan and his wife are extraordinary hosts! You won't be disappointed. And I can't wait to see the Mill when that's finished and open.

Highview Country Escape - Cozy Cabin with a view
What an incredible stay we had! The cabin is spotlessly clean and beautifully decorated with a warm and cozy vibe. The hosts thought of everything that could possibly be needed and were extremely responsive and helpful with anything we asked. The surrounding land is an oasis of peace and relaxation with so many spots to check out. We loved winding down in the hot tub and checking out the farm animals down the road. The pond is another amazing spot! All in all, we highly recommend this airbnb and we really hope we can come again.

Galena Cabin, Access to Owners Club, Privacy
We loved the home, and enjoyed our peaceful time there. The patio was great!

Aspen House - A Private Quiet Getaway In Nature
Hailey was an excellent host. The Aspen House is beautiful. It was the perfect size for our family of 6. It has everything you could need. We really liked that there were plenty of blankets and entertainment outlets. Our youngest was excited to see that one of her favorite spiral toys was there. We had to leave abruptly in the wee hours of the morning due to a sick kid and Hailey made check out a breeze. We were grateful as she ended up being pretty sick. We will definitely look to stay here again when we're in the area.
House rentals in Galena

Cozy private brick loft by downtown-free parking
We absolutely loved our stay. The place was beautiful and exactly as described. Very clean too!!! We loved the binder with information in it and reading all of the facts about the place. Great stay!!!

The Car Wash Inn A Unique Stay
Our stay at the Carwash Inn was lovely!! The space is cozy and was perfect for our needs. The whole place was very clean and the bed was very comfortable, would recommend!

Galena home close to Main St with parking and deck
Super cute place! Having the 4 bedrooms was great for our small group of girls. The dining and living room had the right amount of seating. We didn’t have to hop in the car to explore town. All the restaurants and shops were within walking distance but the location was on a side street so it felt private. I definitely recommend Deb’s place!

Modern/Historic Mansion
Everything was great!

Galena RowHouse - Downtown with parking included!
From making the reservation through check out Mary was great to work with. The property is just as described and a wonderful accommodation for a bachelorette gathering of 9+1 infant. The house was well furnished with comfortable beds and lots of extras that made our stay extra special. Having private parking was a big plus. The house is within walking distance of restaurants and shopping. Our group loved the private porch area for gathering. We never ran out of things to do! We highly recommend the Rowhouse and Galena for a fun weekend getaway.

The Downtown House - 1820s home steps from Main St
Awesome find a block from Main Street in downtown Galena, we’ve stayed here several times and are constantly impressed. Lauren has done a great job taking an older place and making it modern without removing the charm. Everything from Bluetooth speakers to a modern kitchen and large TV with online services and WiFi, this is a great place to stay w family. They even have a parking spot a block away now. Lauren is an amazing host and responded immediately to any request as she’s right down the street. The only downside is on a weekend night it can get a bit loud being one block from several bars, but that’s the nature of being downtown . Highly recommended!

Adorable 3-bedroom Modern Home
From start to finish, this was a great experience. The description and pictures matched and our party of 7 definitely fit comfortably. We cooked a few meals and had every pot, pan, and utensil I needed as well as a full grocery store about 5 minutes away! The price was also very reasonable.

3bed 2bath nestled in cozy Grandview neighborhood
Thank you for your hospitality, great place at a good price. not to far from other good establishments.
Condo rentals in Galena

Lake Links Loft in Galena, Illinois
Our family had a fantastic job at Dan's place. The location is great - close enough to the Eagle Ridge Inn and Owners Club, but very private location with a beautiful view of the lake. The unit had everything we need and was much larger than the pictures made it seem. Galena had great shopping and restaurants. Galena Territory Owners Club indoor pool was perfect for the kids. I'd recommend staying here anytime we make it back to Galena Territory!

Long Bay Point Unit C5
My husband and I stayed here for 4 nights. It's a 10 min drive from downtown Galena in a quiet wooded area with paved trails that you can take to the nearby amenities. The place was clean, quiet, and the bathtub was amazing! The gym and indoor/outdoor pool are very nice but about 1.5 miles from the condo which wasn't stated anywhere (or at least not anywhere we saw) and was a little disappointing but overall wasn't a huge deal. The restaurant is a short walk through the trails or you can drive to it. It's right next door. Also, the initial message you get after booking with the rules and asking to email them out of the app was a little daunting and not normal for Airbnb bookings. It just had a less "homey" experience that you expect from Airbnb. It made me slightly nervous but after everything I would certainly stay here again.

Access to Pools and Lake Galena Marina #Dog Friend
Absolutely amazing stay in Galena! We felt right at home. It was a perfect distance away from downtown, which was easily driveable, and absolutely quiet surroundings. We had everything we needed and was a great set up! Great communication with host and detailed responses about restaurant recommendations, directions to the home and check out instructions. Absolutely a must stay when traveling to Galena!

Montana House #302 - The Luxurious Downtown Stay
Amazing location and incredible amount of work went into restoration. Clean and easily accessible

Galena, IL, 2 Bedroom Q #2
Very nice place. I would definitely stay there again!

Driftless Get Away
i liked that it was accessible to main street. walking distance. it was however very noisy. Semis running by all Friday night. I loved the decor of the rooms. it had that old feel to it. reminded me of Grandma's place with the creeky floors. very roomy.

Tranquil Retreat: Cozy 1BR Suite @ Wyndham Galena
The place is about 5 miles from Galena but not a bad drive to town. If possible, stay in a suite that has a view. Beautiful to wake up to & star gaze at night. The pool is big, the hot tub is hot, the fitness center is well-equipped, & the kid's rec room also. The lobby is huge with a nice fireplace. The suites are large & like a nice, small apartment. It was fun going thru the many shops downtown. Make sure you take some time to tour Galena's many beautiful old homes & buildings. Visit the visitors center by the river in the old depot & have breakfast or lunch across the street at Ottos'. Love this town!

Gorgeous Riverview condo on the Mississippi
Had a wonderful stay at Barbra’s place. Very inviting an well decorated, beautiful view over the Mississippi River where we viewed gorgeous sun rises and hunter moon reflection over the water. Highly recommend staying at Barbra’s place if your travel’s bring you to this area.
Quick stats about vacation rentals in Galena
Total rentals
180 properties
Total number of reviews
17K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Wifi availability
170 properties include access to wifi
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 vacation rentals with a dedicated workspace in Galena?
Yes! Work meets play with ease at over 70 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 bed and breakfast rentals in Galena?
Experience the best of Galena with our bed and breakfast rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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.
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