Family-friendly holiday rentals in Galena

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 302

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 as a nod to its previous existence as the Grant Hotel from 1895 to 1933. Suite 302 is an ADA accessible unit located on the 3rd floor and can be attached to Suite 301.

Downtown Gem for Two

Newly remodeled downtown apartment right in the middle of town. New furnishings, office nook with desk, full size kitchen and appliances, smart tv, free wifi, large open living space with private bedroom and bath. Very clean. Adjacent shared deck with table and chairs is available for use. This is a second floor apartment in the back of Simply Elegant Boutique so there are 17 steps to get to it from the outside. *Rest easy, every surface and door knob is disinfected after each stay.

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

Peaceful, Cozy Home w/ Club Amenities in Galena.

Welcome to the Toasted Marshmallow; your cozy escape from reality. Enjoy the peace and quiet of this charming three bedroom, two bath home in The Galena Territories. Kitchen is fully equipped to meet your needs. Enjoy the additional lower level family room w/ 2nd fireplace so your group may spread out. Deck with ample room for dining outside and enjoying your coffee or wine. Home includes six access passes to the GTA Owner's Club and pools. Strong Wi-Fi for remote work, if needed.

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!

<-Hot tub-Firepit-Gas Fireplace-Game room->

Enjoy the ultimate summer retreat at our stylish 4-bedroom cabin in Galena Territory! Sip your morning coffee on the deck, then explore nearby trails or relax in the hot tub. Challenge family and friends to arcade games, air hockey, darts, and board games. With 10 amenity cards, access the Owner’s Club for swimming, fitness, and indoor pickleball—rackets and balls provided! Whether you seek adventure or relaxation, this cabin is your perfect summer getaway!

Gameroom in Galena

In the center of downtown Galena, we offer over 1500 sq ft. in a 1852 building. A bay window offers 180° view of Main St. A pool table, shuffleboard, pinball machine and bar are at your disposal. You'll have access to either Main Street from the front or Bench Street from the back. There is free parking on South Main Street and out the back on South Bench Street. There is no dedicated parking spot but parking opens up quit a bit in the evenings.

1103#203 Modern 2BR | En-suite Master | Downtown

Urban charm awaits in this 2nd floor apartment at a Experience comfort in this modern 2BR apartment featuring 1.5 baths and an en-suite master. Located in downtown Dubuque, you’re steps away from the Millwork District’s dining and entertainment. Enjoy a fully equipped kitchen, cozy living area with smart TV, and complimentary Wi-Fi. Free parking included. Ideal for families, couples, or business travelers seeking convenience and style.