Family-friendly vacation rentals in Jo Daviess County

Private, Galena Log Cabin

This custom log cabin is the perfect getaway for friends & family seeking the solitude of the Galena Territory and fine dining and shops just 10 minutes away on Galena's Main Street. Each of the 3-levels offers an owner's suite with bath. Cozy up to 2 fireplaces, grill on the deck, or make 'smores at the firepit. The cabin has high speed, fiber internet and the lower-level walkout features a 55” flat screen TV. Guests can access swimming pools & pool tables at the Owner's Club 7 minutes away.

Pet friendly, 2 BR close to Mississippi River

This comfortable home is a 2 BR 1 BA with a full kitchen, and off street parking. It is 1 block away from the Mississippi River and within walking distance to local shops, restaurants bars, parks, and walking trails. The local grocery store is located directly across the street. Well behaved pets are welcome. The backyard is completely fenced in. NO SMOKING INSIDE. As stated in the other notes section, we are located along the Canadian Pacific Railroad and there will be trains going by.

Ulysses Suites, Suite 202

Ulysses Suites has just been completed inside the historic J. G. Schmohl building in the heart of downtown Galena, located at 213-217 S. Main Street. The location is walking distance to all the best restaurants and shops. We have 7 suites and a beautiful lobby that are modern and luxurious, with lots of historical character and texture as a nod to its previous existence as the Grant Hotel from 1895 to 1933. Suite 202 is a gorgeous studio with a huge window seat looking over Main Street.

*Winter Fun* *Hot tub-Fire-3 king beds-Game room*

Relax, unwind, & explore at this winter retreat in Galena Territory! Escape to this cozy, spacious cabin for a peaceful winter getaway. Sip morning coffee as snow falls through the trees, then unwind in the hot tub or by the fireplace. Roast marshmallows around the fire or enjoy arcade games, air hockey, darts, and more indoors. Stay active with access to the owner's club—indoor pool, fitness center, and pickleball (8 amenity cards included). Perfect for relaxation and winter adventure!

Octagon treehouse Hottub-pool-fireplace-firepit

Unique "tree house" - an octagon tiny house, surrounded by the woods! 2 bedroom, 2 bathroom home you can enjoy the views of nature all around, with floor to ceiling windows. One king bed, one queen bed. Modern comforts with fun flash blacks. Private hot tub and firepit look into serene woods! Sit by the indoor gas fireplace and enjoy our record collection. Soak in a Japanese soaking tub. Enjoy fall colors or watch snow fall! Community indoor poor, seasonal outdoor pool, gym access

Galena Country Getaway

Brick walkway leads to the cedar deck with Adirondack chairs overlooking the large backyard. Enjoy dinner out on the deck and roast marshmallows over a bonfire at the firepit. The dark sky provides excellent stargazing. Kitchen features full-sized refrigerator, cooking utensils and a variety of spices. Spacious bathroom with a waterfall-style shower. Carpeted loft includes a sleep number queen sized bed and two twin beds. Close to Historic Galena & Apple Canyon State Park

Beautiful Miner's Cottage in a Garden

This 1840's miner's cottage in the heart of Galena is only 3 blocks from beautiful, historic and fun Downtown Galena Main Street, but is far enough to have quiet times in the quarter acre yard of perennial gardens as well the expansive 2 story front porch, and 3rd porch off the kitchen, with gas grill. The house sits on a corner lot in the Galena National Historic District. The bathroom and kitchen are newly remodeled and the entire house is designer decorated. Beautiful!

Aspen House - A Secluded Getaway In Nature

Relax with your loved ones at the peaceful Aspen House. A Miner's Cottage nestled in a beautiful stand of aspen trees = a quiet retreat just for you! The property is surrounded by protected wooded green space with the Taylor Run trail adjacent on the northwest side. The Owners Club, pools & lake are accessible by hiking/ 5 minute drive. Enjoy bird watching, fishing, hiking and picnicking without driving anywhere!

Hot Tub + Fall Views | Peaceful Escape

Welcome to Pine Ridge—a peaceful, modern 2-bedroom, 2.5-bath vacation rental in The Galena Territory. With two king suites, a cozy living area, forest views, and a private hot tub, it’s perfect for couples, friends, or a remote work getaway. Relax on the porch, unwind by the fireplace, or explore nearby trails, shops, and GTA amenities. Just 5 minutes to the Owners Club and 10 minutes to downtown Galena.

Tree Tops

So much more than just a place to sleep! Tucked away in a cedar forest and built on stilts reaching the tree-tops, this eco-friendly, African-inspired lodging experience is one of a kind. Located on the owner's ranch in the rolling hills 12 minutes from downtown Galena, you feel as though you are nestled in the heart of nature. Horses, alpacas, and mini donkeys roam the secluded 37 acre property.

The VIP Room at The Cathouse Suites, Dogs OK w/$$

Newly renovated building in historic, Uptown Galena above Miss Kitty's Grape Escape. One studio apartment with kitchenette with microwave and coffee/kcup maker, queen size bed, 4K TV, & Wheelchair accessible patio. Extra mirrors in the bathroom with a full size shower, bathrobes and lush towels. Easy access to premier night life and entertainment just below at Miss Kitty's Grape Escape.

Cozy Galena Townhome

This renovated 2-story, 2-bedroom townhome plus loft is located in the Galena Territory, a 6800-acre resort area with beautiful rolling hills, 24 miles of walking trails, golf courses, and amenities. Located in the Creekwood townhomes, it's less than a 4-minute drive to the Country Store, Highlands Restaurant, and Thunder Bay Falls. Kick back and relax in this calm, modern space.