
Vacation rentals in Galena
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House rentals in Galena

Comfortable 4 Bed 4 Bath in the Galena Territory!
Beautiful place and James is very good host . Thank you

Peaceful, Cozy Home w/ Club Amenities in Galena.
We enjoyed our stay. It was a great location to Oak hills farm. We traveled with kids and the amenities available was very helpful to our stay. Great house to stay overall.

Historic+private brick loft by colleges & downtown
Nathan's place is a comfortable haven with character. We especially appreciated the location: easy walk to grand, historical homes on the bluff; historic districts downtown; and even a small market just blocks away. The home is clean and spacious, with tall ceilings, transom windows, and lovely, restored wood floors. The small kitchen is remarkably well stocked. Even on a busy, holiday weekend we slept soundly, thanks to blackout curtains, ceiling fans and a white noise machine. We highly recommend this stay for budget conscious travelers like us who want to explore the heart of this beautiful river town.

Galena home close to Main St with parking and deck
We had a mother/daughter few days and Deb’s place was perfect and met all of our needs!! Great place to stay!!

The Downtown House - 1820s home steps from Main St
Lauren's home was lovely and she was wonderful to have as a host. She was proactive with sending check-in and check-out information and provided ample information prior to arriving. The house is super close to the main streets in Galena, which made it very walkable and easy to get back and forth while taking a break or dropping purchases before meals. It is on the corner and could be too noisy for some but it didn't bother us too much. You can tell it is an older home - some unevenness to floors and tight bathrooms - but lots of character and really convenient. All in all I would recommend and would stay again!

Galena Getaway
What a perfect place for us! From the wrap around porch to the two fireplaces, this place is so dreamy! The showers were great and the beds were so comfortable. The kitchen had everything we needed and more. We will stay again if we get the chance!

A MUST SEE! 2BR Lakefront Home w/ Boats & More!
Great place! We felt right at home. Very clean and beautiful surroundings!

Hot Tub-Dog friendly-fire tables-pools
Doreen’s place was spacious, comfortable, and had everything we needed for a relaxing stay. The screened-in porch and outdoor deck offered a peaceful and serene atmosphere. Having multiple bathrooms was a major convenience, especially for our group of six. We also really enjoyed the amenities at the owner’s club, particularly the pool and fitness center. Doreen was incredibly responsive and helpful throughout our stay.
Condo rentals in Galena

Montana House #201 - The Luxurious Downtown Stay
The filmmakers attending the Julien Dubuque International Film Festival (JDIFF) loved staying here! It was a perfect place to be!

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!

Galena, IL, Studio 2
Great place to stay very close to downtown Galena.

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.

Tranquil Retreat: Cozy Studio @ Wyndham Galena
This place was absolutely B.E.A.U.T.F.U.L! The staff were super sweet and friendly. So many things to do at Galena. Also, there was a table with “to do activities” That was very helpful. I would 100% come back. Thank you all staff for being such a good host.

Driftless Get Away
We had a wonderful five day stay at the driftless getaway! Everything was to our expectations and beyond. Nice little touches throughout the entire areas. (Love the twinkle lights) There were Activities for both kids and adults like games and coloring books provided in the space. As well as a coffee bar, retro mini fridge and treat baskets in each room. Our location was a quick 4 minute drive or 15 walk into the main street of Galena. The town is charming and there is plenty to see, eat, do. Wouldn’t hesitate to stay here again! Thank you both for such a lovely home away from home!

Enjoy our Lake Views this Spring! King Bed, Screen
A beautiful place in a great location. Just minutes from all the golf courses. The home was extremely well kept and updated. The sunroom was awesome.

Gorgeous Riverview condo on the Mississippi
This was a very well maintained and clean location. Great balcony to watch the river traffic. Walkable to restaurants Very enjoyable
Dog friendly vacation rentals in Galena

The Gathering Place- Modern, Spacious, 6 bedrooms
Perfect home for extended family to celebrate together! Everyone was thrilled to have their own bathroom and big, open common areas to hang out together. Great fire pit, hot tub and yard area. Home was well stocked & very clean plus near walking trails, golf & owners club.

131 Plum Cove - 3 Beds, 3 Baths, Sleeps 8
We had originally booked 2 nights, but had such a great time and felt so at home staying at Michael's place that we decided to extend our stay for an extra night. It felt so peaceful and relaxing and even the kids were begging to stay another day. Luckily it was available. Everything was very clean and we loved the style and decor of the house. The view from the balcony was beautiful and perfect for enjoying an early morning cup of coffee. The house had everything we needed for our stay with kids and dogs. The kids loved that we had access to the pool at the owners club and the dogs loved taking walks down the path by the lake. Also, Michael was very responsive throughout our stay. We had an issue with one of the TV's and within 10-15 minutes the maintenance guy was there and able to get it up and running. This place is definitely at the top of our list the next time we visit Galena!

Cute cottage, short stroll to Mississippi River!
This place is a beautiful little getaway. Right up the road from the river, it is peaceful and quiet. Lots of fun architecture to see in town and the river walk is lovely. Our dogs were welcomed which made the trip 10x more enjoyable. The house is cozy, warm and feels very much like home. Sue has an entry table in the home with suggestions for local activities, eateries, shopping which was nice to refer to. Overall we were happy with the space. It was nice to know that Sue was in the house next door for questions, but she very much provided privacy unlike some places I’ve stayed. I highly recommend!

Cozy Retreat | Hot Tub | Firepit | Dog-friendly
Brian and Jonny were very responsive and communicative from beginning to end. It was a last minute trip and we were lucky to find a pet friendly place during the start of the summer season. The house was clean, cozy and close to walking trails. Although we did not take advantage of the outdoor grill or hot tub (they have a wood burning fireplace for the winter), we enjoyed the screened in porch and open concept layout of the house, as pictured in the profile. The house is situated between two other houses blocked somewhat by the trees. I would describe as semi-private where we could see their back patio/hot tub/fire pit and vice versa. But whatever your personal comfort level, you can’t beat the proximity to trails, Owners Club, and easy access to Hwy 20 to Galena! We enjoyed our stay and exploring!

Galena Cabin, Access to Owners Club, Privacy
Joel’s place was absolutely beautiful! It was secluded and peaceful but also very close to down town. I loved drinking my coffee outside in the mornings it was so peaceful! I’d recommend Joel’s air bnb to anyone wanting to travel to galena. I’d go back in a heartbeat! Joel was a great host. He gave us all the information and checked In on us throughout our stay. We had a great time!

Modern Space on Main with On-Site Parking!
The property was cool. Though I did realize how out of shape I was - winded every time I climbed the 2 steep floors to the unit. But so worth it. Spacious, adjustable climate (HVAC), TV, sprawl-able sofa and leather chairs. I was looking forward to having my coffee and reflection time on the back porch but, alas, the weather didn’t cooperate. Several dining options nearby and we walked over to the Fenelon Elevator for an epic view of the Mississippi River. Thanks for the memorable stay - it made a perfect landing on our adventure along the Mississippi River, from the headwaters in MN to the Gulf. Our Tip - Drop in to the Wicked Dame wine bar. - what a cast of characters we encountered.

Aspen House - A Private Quiet Getaway In Nature
We had a really wonderful stay here over Memorial Day weekend. My two and four year old loved the toys and the movie screen (our daughter cried when we left). My husband and I thoroughly enjoyed the screened in porch. We’ve been to Galena now many times and this was our favorite place we’ve stayed at yet!

Summer Fun! Game Room! Close to all amenities!
We had a wonderful time. Great location. Private and lots of room! And if your a vinyl fan it was so much fun!! We will be back again !
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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