Holiday rentals with outdoor seating in Jo Daviess County

Chelsey’s condo is the perfect city escape due to its idyllic location in a wooded setting that makes it an oasis for any traveler. The unit itself is well appointed with comfortable beds and is incredibly clean. Don’t look any further if you’re planning a visit to nearby Galena!

This was our second time at Jennifer's place and it was just as perfect as it was the first time. We brought our daughters with us this time, and they slept on the pull out couch and loved it. It was the perfect space for our family. The amenities are a plus. We went to the indoor pool at the Owners Club which was nice and enjoyable and we played the board games one of the nights, which were provided. I highly recommend this place. It's quiet, peaceful, there are walking paths, and it's about 10 to 15 minutes from Main Street. We will definitely be back!

Great place! We felt right at home. Very clean and beautiful surroundings!

The Ravine Lodge is a relaxing spot to truly getaway and unplug. A short distance to downtown Galena and a few miles to the main Owners Lodge where the pool and gym are located. Windy roads so driving at night may not be ideal for some. Home was very clean and had all the amenities. We would come back!!

We had a great stay at the cabin for my brother’s bachelor party weekend. We played 2 golf courses, ate at one of the resort restaurants, and went downtown for dinner one night. It’s a 2 minute drive to the courses and 10 minutes to downtown. Great location that sat on one of the par 4s.

Perfect stay for our girls’ getaway! We stayed here to celebrate our bride-to-be, and it couldn’t have been more perfect. The place was beautiful, clean, and had everything we needed for a comfortable stay. The location was amazing—just a short distance from the shops in Galena, which made exploring so easy. It was the perfect spot to relax, enjoy time together, and make special memories. Highly recommend for any group looking for a charming and convenient stay!!

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!

Even better than advertised. Sandy was wonderful and so was the home. We were very pleased with our stay and her communication. The house is in a nice, quiet neighborhood, close to the strip, around golf courses, wineries, great food, fishing, historical places, and kayaking. Thanks again Sandy, we will be talking to you soon I’m sure.

This was my fourth time staying at Sandys and each time is just as enjoyable as the last. Her new wallpaper in the kitchen, bedrooms, and master bath are beautiful. She has a real knack for decor. She's always super helpful, kind, and her breakfasts dont disappoint! If you're looking to relax in a peaceful setting, but still be close to downtown Galena, this is THE place to stay.

This is the second time we’ve stayed at this Airbnb that Diane owns. The place is beautiful and comfortable and the location is ideal for spending lots of time downtown walking, eating, and drinking. No need to drive! We will for sure be back here again. The bed is so so so comfy!!!! Diane does an amazing job of making the place feel welcoming. She is also flexible with checkin which was a lifesaver for this trip! Can’t wait to go back! Thank you Diane!

We had a fantastic stay at Joan’s place! Everything was spotless, beautifully decorated, and the location was perfect. We will definitely stay here again and highly recommend it to anyone visiting Galena.

I would highly recommended staying at this airbnb!!

My daughter and I really enjoyed Debra’s cute, cozy, charming and spacious place. It was clean and well kept. Being within walking distance to shops, restaurants , and everything else was just great. We would stay here again! Debra was super responsive and helped us with any need we had!

Awesome location. The place had everything we needed and was very clean. It was loud sometimes but it was really more because of the clientele at the bar across the street than The Grape Escape. Closing the windows and turning the air on helped a lot. Plus she does provide earplugs if needed. We would stay here again for sure!

We had a lovely stay at Albert’s Glen while passing through Galena on our way to St. Louis. I scored a few bonus points with my husband when he found out we’d be staying in a historc brewery—with a sauna. The space is full of charm and thoughtfully designed touches that made me feel at home. The bed was comfy (especially if you like a firm mattress, like I do), and the water was hot—just what we needed after a long day of motorcycle riding. It’s a short and pleasant walk to downtown, where we enjoyed dinner on the terrazza at Vinny Vanucchi’s and breakfast at Otto’s. Next time we’re in Galena, we’ll be sure to stay longer so we can explore more—and hopefully catch Sandra’s Sunday breakfast!

We will be back! The suite was easy to find, very accessible to Galena's very walkable downtown, yet felt very private. The cleanliness was 10/10. The space itself was inviting and comfortable. The multiple master suites made for a very comfortable stay, and the bright, inviting kitchen, dining and living rooms made it a joy to relax between trips spent wandering the downtown area. A fantastic experience overall!