Holiday rentals with breakfast in Galena

The Persian Room @ The Painted Cat Bed & Breakfast

Welcome to the Painted Cat of Galena, a cozy Victorian B&B with feline flair! The Persian Room is pink, playful & the perfect place to experience Victorian glamor. Featuring a cozy sitting nook in the bay window, you'll find amazing views of the historic neighborhood. Also features an ensuite bathroom with a pink claw-foot tub. Includes a Roku HDTV, window AC, electric fireplace and steam heat. Daily breakfast included with your stay! Proudly welcoming cat lovers of all stripes 🏳️‍⚧️🏳️‍🌈

The Farmhouse country ranch

Relax by yourself, with friends or the whole family at this peaceful country spot -limited cellular. Explore Jo Daviess county in the northwest corner of Illinois and surrounding areas staying in a recently renovated country ranch style house located on a 150 year old working farm. Perfect get away from the fast pace busy life for those who want to take a quiet break, history buffs, explorers, and making lasting memories with family or friends. Enjoy animals, hiking, fishing, history plus more.

Gypsy Coach Sanctuary

Step into a soulful hideaway in this restored 1860s country church—nestled in the heart of the unique Driftless Region of southwest Wisconsin. Just minutes from the Dubuque Millwork District & River Museum, historic Galena, Potosi Brewery and the University of Wisconsin Platteville, this once holy haven offers peaceful country views and timeless charm. A serene retreat where kindred spirits, dreamers and wanderers can rest their boots and stay awhile—close to the excitement, yet a world away.

Galena home close to Main St with parking and deck

Charming four-bedroom house located 2 blocks from Galena's Main St. Fully-equipped kitchen, dining room, living room, and laundry room. Direct TV and WiFi are also available. One bedroom is on the main floor, 3 are upstairs. The home has a large front porch with a porch swing. There is also a deck with lots of seating built into the back hillside which is shaded in the afternoon. Two concrete off-street parking spots between the house and deck are available for guests. Easy self-check-in.

Family summer retreat! Firepit-Gameroom

Perfect Summer Escape for Your Crew! 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 8 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!

Cloran Mansion (Antonio's Cottage) (Pets Allowed)

Adventure into historic charm with modern comforts! The Cloran Mansion Bed and Breakfast offers a perfect romantic getaway, complete with beautiful gardens, a koi pond, gazebo, and firepit. A tasty and filling breakfast (served between 9 and 10:30) gets your day off right. Located on 1.5 acres, the Cloran Mansion gives guests plenty of opportunity to relax, yet it is just a three-minute drive to Main Street and the shops and restaurants of Galena. The Cloran Mansion was built in 1880.

Galena Retreat-Cogan View!

Galena Retreat with Amazing Views +Hot Tub and Resort Amenities. Relaxation awaits you from this one acre property. Elevated with unobstructed views of the rolling hills, enjoy watching sunrises AND sunsets. Located centrally to all the wonderful things the Galena Territory has to offer. Guests will enjoy being steps away from the Owner's Club and close proximity to Eagle Ridge Resort, 4 golf courses, hiking, the marina, Shenandoah Riding, Chestnut Mtn. and Downtown Galena.

Intimate Unit w/ Authentic Irish Ambiance+Shuttle

We welcome you to experience the charm of Ireland in the heart of Galena. Our boutique property blends warm hospitality with thoughtful details, from inviting guestrooms to cozy gathering spaces. Just minutes from historic Main Street, you’ll enjoy strolling past shops, galleries, and restaurants. The rolling hills of Jo Daviess County offer hiking, scenic drives, and vineyard visits. After exploring, return to the comfort and character that make our inn a true getaway.

Greenbriar Country Suites

An oasis of country charm located in the heart of Galena...Free private off street parking and just a short stroll from restaurants, museums, shops and historic sights. Individual Suites from $138.75 to $185 plus tax Free breakfast provided on full price mornings. 24 hour security and maintenance on property. Licensed and inspected by the City of Galena and Jo-Daviess health department. Sleeps 14 people. No common areas for gathering or meetings, no kitchens...

Riverboat Suites - Room 1

Enjoy easy access to everything in historic downtown Galena including popular shops, restaurants and museums from this top rated bed and breakfast. The Riverboat Suites has earned accolades for its outstanding customer service, affordable pricing, high end amenities and terrific location. While Room 1 is our most basic room (and only room with a detached private bath), it offers a comfortable queen bed, yummy breakfast buffet and an impeccably clean space.

The Skylight & Whirlpool Suite On Main St. Galena

The Skylight Apartment is conveniently located in downtown Galena at the quiet, north end of Main Street near restaurants, shops, and night life. We offer private on-site parking — safely park your cars worry-free in the parking lot behind the building. Relax on the private outdoor deck, or lower level meeting room. Visit our FAQ page by searching "305 N Inn Galena" Check out all our listings at Airbnb.com/p/galenaapartments ( copy & paste into URL)

Standard Room

Betsy's Room is located in the White House, a refined, elegant colonial revival-style home. Betsy’s, named after the youngest daughter of Bill and Elizabeth, is an elegantly adorned, spacious room with a queen bed and window facing the river. The private bathroom is located across the hall. Enjoy hiking the trail or sit outside and relish views of the Mighty Mississippi from the patio!