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Galena Getaway

Peaceful, pet-friendly ($50 fee per reservation) vacation home in the Galena Territory. 3 bedrooms, 3 bathrooms, two living rooms, 2 wood fireplaces, screened in porch, upper level porch, deck, firepit, access to owner's club (pool, exercise room and game room), marina and 24 miles of hiking trails. Sleeps up to ten people. (Please ensure your guest count is accurate when you make your reservation. The guest count can be updated if needed. Inaccurate reservations will be charged accordingly. )

The Brick Apartment Main Street Galena

Hello! Welcome to our beautifully-renovated apartment, conveniently located on the north end of Galena’s historic Main Street. This unit is above Big Bill’s coffee shop, and boasts exposed original brick from the historic Logan House Hotel, hardwood floors, a kitchen (range, refrigerator, microwave, sink), and beautiful views of our historic town! Only feet from restaurants, shopping, and night life, this apartment allows you to explore Main Street without the hassle of re-parking! See you soon!

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.

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.

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

Family-Friendly Wooded Retreat- 3 Ensuite Bedrooms

Loved by guests for its cleanliness, location, and value, this spacious 3BR, 3.5BA home is perfect for families, families traveling together, or groups of friends. This Galena Territories retreat is steps away from the Owners Club, Marina, and championship golf courses. After a day exploring, unwind in two comfortable living areas and enjoy private en-suite baths in every bedroom. Surrounded by wooded views, this home offers ample space to relax, recharge, and reconnect with nature.

Hot Tub Retreat|Summer Nights · Fall Colors Await

Welcome to Shenandoah Ridge—our thoughtfully designed 4-bedroom, 4.5-bath vacation rental tucked into the woods of The Galena Territory. Spacious, peaceful, and full of cozy touches to help you unwind. Whether you’re here for a family getaway, group trip, remote work retreat, or just time in nature, you’ll find everything you need to feel at home. Just 7 minutes to the Owners Club and 15 minutes to downtown Galena—close to the action, but still calm and quiet.

<Hot Tub><Fire Pit><Game Room>3 Kings! Family Fun!

Ultimate Family Escape in Galena Territory! Unwind, explore, and make memories at this chic, spacious cabin! Sip coffee on the deck as deer wander by, soak in the hot tub, and gather around the fire pit for s’mores. Stay cozy by the wood fireplace or challenge the family with arcade games, air hockey, pinball, and darts! Enjoy Owner’s Club access with a pool, fitness center & pickleball (8 amenity cards). Adventure awaits—book your perfect getaway today!

A MUST SEE! 2BR Lakefront Home w/ Boats & More!

Welcome to our cozy lakefront home located in East Dubuque, Il which is only minutes away from Galena, IL and Dubuque, IA. This two bedroom home sleeps 6. We provide canoe's, and lifejackets. This home also has a large garage, a private deck overlooking the lake, and large yard. Other amenities include central air, comfy mattresses, all kitchen appliances, washer/dryer, Smart TVs with sound bar, and cable Internet. Don't miss out book now.