Holiday rentals with outdoor seating in Galena

Our cabin's a win-win

In 1834, it was a chicken coop nestled between the house and barn. Today, it's a cozy cabin just a stone's throw away from the villa and venue. From the private, rural setting to the rustic decor, you'll feel as though you've traveled back to simpler times. It's unique, refreshing and oh-so tranquil. If you're looking for a little hush and a lot less rush, you're going to fall in love with this little home away from home. While you're visiting, get the scoop on how we transformed this coop.

*Holiday Getaway! Fireplace, Hot Tub, Fire Tables*

Step into Rolling Hills Retreat, a sanctuary from the everyday bustle! Our dog-friendly rental offers breathtaking views and numerous amenities for your pleasure and relaxation. Enjoy a swim in the indoor or outdoor pool, and discover a variety of amenities that promise an unforgettable stay. *Pickle Ball *Basketball *Pool Tables *Hiking Trails *Workout Room *Tennis Courts *Brand new (June 2024) Marina with boat rental (additional charge) *Ping Pong tables *Arcade *Scenic Waterfall *Kayaking

*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

1842 Bavarian Brew House

Nestled in charming and historic Galena this beautiful home was built in 1842 by brewer Peter Specht from Bavaria. The cellar operated as his brewery and tavern while living in the home above. The house was extensively renovated in 2008. It remains full of character and charm, but now boasts an abundance of modern comforts. A quiet private patio and yard are the perfect spot for a morning coffee or a glass of wine. All within a few walkable blocks to Main Street, the heart of Galena!

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!

Suite Victory #4 On Main St w/Reserved Parking

Suite Victory #4- Beautifully renovated apartment on Main St. right where you want to be with Reserved Parking. Dining, entertainment, and shopping just outside your door. Open floor plan with beautiful views of downtown Main Street. King bed. Double sink vanity and large walk-in shower. Kitchen has island, quartz countertops, and new appliances. Stackable washer and dryer within the unit. Above Charlie’s Place Eatery on Main Street. MAX 2 PEOPLE. NO DOGS ALLOWED.

Ulysses Suites, Suite 201

Ulysses Suites has just been completed inside the historic J. G. Schmohl building in the heart of downtown Galena, located at 213 to 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 201 is located on the 2nd floor.

Home by the River

Situated alongside the Mississippi River, wildlife abounds in every season. With eagles nesting nearby, there is always something new to see from the beautiful sunrises, cruise ships passing by, and watching the commerce of the barges and railroad right out the front window! This home has been recently refurbished and sits at the edge of our 15 acres. You can see us and visit with us if you like, or you can maintain privacy 10 acres away!

2 Bedroom Townhouse w/Soaking Tub + Rain Shower

Welcome to Dear Galena, a modern Zen retreat on a corner-unit townhouse golf villa with a wooded view. It's the perfect getaway for couples, friends, family or just you! Situated within The Galena Territory and near Eagle Ridge South Golf Course, this townhouse has two bedrooms - each with a king size bed and two bathroom. A pull out sofa bed for additional guest and high-speed Wi-Fi for streaming and all of your work from home needs.

The Car Wash Inn A Unique Stay

Enjoy a unique stay inside a beautifully revitalized single bay 1950s car wash. Only minutes away from historic downtown Shullsburg. This space has been thoughtfully designed to retain it's industrial charm with a nostalgic ambiance, while offering modern amenities for a comfortable stay. ~20 miles to Galena, IL ~25 miles to Mineral Point, WI ~25 miles to Dubuque, IA ~ATV Trail Access with large parking area