Villa holiday rentals in Galena

Captain Merry Bluffside Villa

Bring the whole family to this great place with lots of room for fun. A few minutes away we have several marinas, restaurants, casinos, and the Mississippi river museum. Galena is just 11 miles away with alot of fun things to do. Fall time is beautiful here with the color changes of leaves. Also, the property is right in between 2 ski resorts. Less than 10 minutes from Sundown and 20 minutes to Chestnut ski/ Snowboard resort. This is a perfect place to stay for ski trip.

1869 Historic Italian Villa on the Bluff

This special place is close to everything, with spectacular view of downtown Dubuque and the scenic river. This house which was built in 1869 is one of the oldest homes in Dubuque with close proximity to the historic 4th St. Elevator and walking distance to shopping and main street Dubuque. The Italian villa has a 3rd floor cupola with a fantastic must see view. This is a new listing for the Dubuque area. Looking forward to having you as our guest!

Captain Merry Mansion

A meticulous $2MM restoration revealed the true elegance of this amazing property. Perfect for family gatherings, your own rehearsal or large dinner party. If you enjoy history mixed with luxury, this place is for you. Located by the Mississippi River bridge to Dubuque and only 12 miles from the historic town of Galena, the area offers an abundance of activities. Well behaved children and pets are welcome.

Spring Creek Sanctuary-2BR-Owners’ Club Access

Welcome to Spring Creek Sanctuary! This 2BR/2BA condo in Galena Territory offers comfort and nature. Relax by the wood-burning fireplace, cook in the modern kitchen, or unwind on the private deck with wooded views. Enjoy Owners’ Club amenities—pools, fitness, game room, tennis—plus nearby golf, trails, and Lake Galena. Just 15 minutes to historic downtown Galena, shopping, dining, and wineries!

Galena Territory 2BR Condo | Semi-Private Pool

Enjoy nature’s splendor (and a semi-private pool!) at Walnut Hill Hide-a-way, a cozy 2BR/2BA condo in the Galena Territory. Relax in the living room with fireplace, cook in the well-stocked kitchen, or unwind on the deck with wooded views. Perfect for families or small groups, with pool access just a 1–2 minute walk and other Territory amenities to enjoy during your stay!

Winter. Perfected. @ South Course Villa - Scenic,

2 Bedrooms, 2 Baths, Queen Sofa Sleeper in Living Room - Sleeps 4 in beds, Occupancy of home is 6

Cozy Season @ Poplar! Amazing View, Fireplace and

2 Story Golf Villa, 2 Baths (Sleeps 2 in bed + 2 on sofa sleeper)

Cozy Up in Woodland Vista Retreat on Creekwood - F

2 Bedrooms, 2 Baths, Sofa Sleeper, (Sleeps 6)

Fireside & Frosty @ Creekwood Haven-Cozy Retreat w

2 Bedrooms, 2 Baths, Sofa Sleeper, (Sleeps 6)