Kid-friendly holiday rentals in Jo Daviess County

Stayed here for a sisters weekend- and it was great for 6 sisters between the ages of 60-75. Two bedrooms on main floor and 2 downstairs worked great for us. Things were a little dated- but hey- so are we. We had a couple of issues that needed attn and James was most attentive and took care of them immediately. I would recommend. Great value for 6 women with varying needs! Especially loved the hot tub in the natural surroundings!!!

This was a girls trip. We were there Weds-Sun. The house is beautiful and well appointed. Walking distance to everything downtown. Our favorite breakfast spot was right at the bottom of the stairs. Would definitely stay here again!

Our family—including me, my wife, our daughter, and our puppy—had a wonderful time. Ginger was very kind and provided detailed information, including how to use the amenities like the swimming pools. The property was clean, cozy, and conveniently located near downtown, where we had a great time exploring. We’d definitely recommend this place to any family and would love to return on our next trip to Galena.

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!

We had the absolute best time at The Treehouse. It was truly one of the most spectacular places we’ve ever stayed! From the moment we arrived, it felt like the perfect home for a family getaway. The house had everything we could have possibly needed for comfort, fun, and quality time together. It was sparkling clean, beautifully maintained, and the views were just breathtaking. Our hosts were wonderful. They were so kind, responsive, and helpful throughout our stay. We especially loved relaxing by the fire pit, unwinding in the hot tub, and enjoying the peaceful screened-in porch. It was the perfect balance of cozy and fun! Beyond the amazing home itself, Galena had so much to offer. We had a great time exploring the town, dining at local restaurants, shopping, and just soaking in the charm of the area. We’re so grateful for our stay at The Treehouse and can’t recommend it highly enough. We’re already hoping to return for another family gathering next year!

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!

I can’t stress enough what a perfect place this is! Location is ideal and having reserved parking provided a lot of peace of mind. Condo was super modern and clean. We’ll definitely book again in the future!

I would highly recommended staying at this airbnb!!

We had a great stay at Robin’s place! Right in the middle of town. Cute and cozy inside.

Thank you Don for your attentiveness and friendly welcome. Went to say goodbye, but you were off today… Good for you! We throughly enjoyed the games and location. Hoping it won’t be another 2 years before we come back. Maybe it will be through the week next time… nice and quiet today… Lori Johnson/Paul Simpson

Great location to enjoy the downtown area. Very clean and accurate to presentation on site. Host made check-in/access very easy. Highly recommend!

I had a fantastic stay! The place was exactly as described—clean, cozy, and thoughtfully decorated. The location was perfect and made it easy to get around. The host was incredibly responsive and went above and beyond to make sure everything was smooth from check-in to check-out. I’d absolutely stay here again and highly recommend it to anyone looking for a great Airbnb experience!

We had so much fun staying in Catherine’s suite! The location was perfect and we loved the music from the Grape Escape! We would most definitely stay here again!

This place is awesome! We came with our baby and dog and it was perfect for all of us. Place was the perfect size for us and had an everything we needed. Great location close to downtown Galena and other activities. Comfortable bed and it was great to have 2 bathrooms!

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!

Great place to stay very close to downtown Galena.

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.

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.

The place was exactly as described and what we expected. Far enough out of town to not be busy but close enough for a quick drive into town.

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!

The view from this apartment is everything you would want. The river is right there! We spent many hours on the balcony, watching the joggers and walkers on the path, watching the barges and tugs. Inside, the unit is just perfect. I wouldn't change a thing.

Fantastic stay at Elle & Beck's place. Stayed with friends to celebrate an anniversary and the location was ideal to explore all that Main Street in Galena has to offer. Very comfy beds and spacious bathrooms - great to have counter space in an older building's bathrooms which is uncommon and a pleasant surprise. The living area was well appointed with comfortable furniture and was a great space to start the day or unwind after a day's events. Very responsive hosts with great communication. Sincerely appreciated the offer to sent a couple of items that were accidentally left behind - very thoughtful. If you are looking for a great place to stay for 6 guests, you would have a difficult task to locate a better place to stay in downtown Galena than Elle & Beck's. We've been to Galena several times and this was a memorable stay. Our friends that came along raved about the location as well. Should we be looking for a place for 6 on our next stay, this one is at the top of our list.