Vacation rentals with outdoor seating in Jo Daviess County

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. )

Treehouse! 3BR Ensuites•Secluded• Hot Tub•Fire Pit

🌲7 minutes to Owner's Club 🌲10% Weekly Discount 🌲3 BRDM+3.5 BTH (all ensuite) 🌲Secluded + Spacious on 2-acre lot 🌲Hot tub! 🌲Smokeless firepit (wood provided)🪵 🌲Year-round community indoor pool & seasonal outdoor pool 🏊‍♂️ + zero entry kiddie pool 🌞 🌲Open concept main level 🌲Games & puzzles for all ages 🧩 🌲Axe throwing game 🎯 🌲Large connect 4 game & jenga 🌲New & fully equipped kitchen 🍽️ 🌲Kid & Dog friendly 👧🏼🐶 🌲Seasonal valley views 🌲Gym access 🌲High-speed internet

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.

Cozy Wooded Tri-Level In Galena Territory

Relax with friends or the whole family at this wooded and peaceful place to stay in the Galena Territory.Cozy Tri-Level with 3 comfortable bedrooms and 3 baths. Tvs in 2 bedrooms as well as large tvs in the living room and downstairs rec room.Fireplace in living room area.Sit outside and enjoy the scenery on the front porch or back screened patio.Only 6 miles to Downtown Galena .Guests are welcome at Lake Galena,the Owners Club,Restaurants,Pools and Trails.Six Free passes are included.

Hot Tub+ Firepit+ "Tiny"house+ Views+ Near Galena

Tucked away in the countryside of Galena, our charming A-frame cabin is the perfect escape for those seeking peace, nature, and a touch of nostalgia. This intimate retreat blends mid-century modern charm with cozy modern comforts, creating an unforgettable getaway. Whether you’re sipping coffee on the deck at sunrise, soaking in the brand-new hot tub under a canopy of stars, or unwinding by the fire with a vinyl record spinning in the background, every moment here is designed for relaxation.

Family Fun! Xbox-Hot tub-Firepit-Games in/outdoor!

Enjoy the ultimate summer retreat at our stylish 4-bedroom cabin in Galena Territory! New furniture and Xbox just added! Sip your morning coffee on the deck, 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!

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

Custom Floating Suite-HOT TUB!

Enjoy a stay directly on the backwaters of the Mississippi River. This custom cabin is floating right on the water, and you won't find anything like it! Grab your loved one or friend and surround yourself in nature, while soaking in the hot tub on the floating patio, or in the beautiful tub inside. Relax in the king size bed thats in front of one of the two fireplaces. The cabin has everything you need, including a small kitchen. This floating oasis is located at Millennium Marina.

Galena Country Getaway

Brick walkway leads to the cedar deck with Adirondack chairs overlooking the large backyard. Enjoy dinner out on the deck and roast marshmallows over a bonfire at the firepit. The dark sky provides excellent stargazing. Kitchen features full-sized refrigerator, cooking utensils and a variety of spices. Spacious bathroom with a waterfall-style shower. Carpeted loft includes a sleep number queen sized bed and two twin beds. Close to Historic Galena & Apple Canyon State Park

Suite Victory #3 On Main St w/Reserved Parking

Suite Victory #3- Beautifully renovated apartment on Main St. right where you want to be with Reserved Parking. Dining, entertainment, and shopping just outside your door. Open floor plan with beautiful views of downtown Main Street. King bed. Double sink vanity and large walk-in shower. Kitchen has island, quartz countertops, and new appliances. Stackable washer and dryer within the unit. Above Charlie’s Place Eatery on Main Street. MAX 2 PEOPLE. NO DOGS ALLOWED.

Hot Tub l Fire pit I Chestnut Mt I 6 bed I 10 ppl

Escape to your own spacious mountain retreat just 8 miles from historic downtown Galena! 2 min to Chestnut Mountain. Enjoy a brand-new hot tub, fire pit with free wood, gas BBQ, and patio—perfect for summer nights or crisp fall days. Spend your days hiking, golfing, shopping, or taking scenic wine tours. In fall, explore vibrant foliage, festivals, and local charm. After your adventures, relax in comfort and style with plenty of space for the whole family.

Ulysses Suites, Suite 201

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 and texture as a nod to its previous existence as the Grant Hotel from 1895 to 1933. Suite 201 is located on the 2nd floor.