Holiday rentals with breakfast in Galena

Family Fun! <Hot tub-Fires in/outdoor-Game room>

Escape to our cozy luxe cabin in Galena Territory, the perfect retreat for fall! Start your mornings sipping coffee by the gas fireplace, then warm up each evening in the hot tub! Enjoy friendly competition with arcade games, board games, air hockey, and darts. With 10 amenity cards, you can access the owner’s club for swimming and exercise including indoor pickle ball-rackets and balls at the house! Experience relaxation and adventure in this tranquil haven—your unforgettable getaway awaits!

Cozy Cabin by the Pond

Quiet, private country location to relax and unwind. 9 miles west of Dubuque, close to Wineries, Heritage Trail, Sundown Mountain Resort. Cozy cabin and quarter acre pond. Sun yourself on the patio, or nap in the shade of the covered porch. We're sure you will love this space as much as we do. Not suitable for children under 12, we strictly enforce no children and no pets. Outdoor relaxing space, gas grill. Fully stocked cabin, with breakfast items included for you to enjoy at your leisure.

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.

The Tabby Room at The Painted Cat Bed & Breakfast

This regal room is adorned with stately green damask wallpaper and a large central window overlooking historic Park Avenue. Spacious and inviting, this room makes quite an impression. It also includes an antique record player and an ensuite bathroom with a clawfoot tub. Includes a Roku smart tv, window AC unit and steam heat. As part of The Painted Cat B&B, a light, self-serve breakfast and coffee is served daily with a plated brunch served every Sunday. Breakfast included with your stay.

Cloran Mansion (Ann's Room) (No Pets)

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.

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.

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!

Luxemburg Beauty- The Gehlen House Inn

Nestled in the rolling hills of northeast Iowa, the Gehlen House offers year-round accommodations for calming getaways and/or family fun. One of 34 area buildings listed on the National Register of Historic Places, the Gehlen House Inn has 6 bedrooms, 6 baths, a shared kitchen and living room space. Kalmes Restaurant is directly across the street.