Holiday rentals with outdoor seating in Jo Daviess County

4.99 out of 5 average rating, 368 reviews

The spacious interior showcases a cozy seating area with a brown couch and decorative pillows. A large bed is centered beneath a wooden beam ceiling, framed by patterned curtains. Unique artwork adds character, while a game table occupies one corner, enhancing the inviting atmosphere.

Guest house in Galena

The Guest House - Private and All Yours

*Some revenue from your stay will go to SPLC, ACLU, and other progressive causes* Enjoy the cozy comforts of this renovated studio in Galena's historic district. The building is yours for your stay, with driveway parking onsite. We've made this a welcoming space for respectful travelers of all backgrounds, so join us for a comfortable and unforgettable time in our beautiful and historic city. Our space is privately operated by us, not a rental company. We live onsite, and been here for 20 years.

4.99 out of 5 average rating, 101 reviews

A recreational area features a blue ping pong table next to a classic billiard table. A stylish bar with modern stools is positioned against a floral accent wall. Natural light illuminates the space, enhancing the inviting atmosphere for leisure activities.

Cabin in Galena

Secret Room-Fireplace-Hot Tub-Pool/Marina,Patio

Enjoy this gorgeous, huge home for your group getaway! Relax in this tranquil wooded setting with a private hot tub or soak in the luxurious tubs. Hang out in the "Secret" room with motorcycle bar & TV, drink coffee in 3 seasons room 4bed/4.5 bth home is spacious with multiple spaces to enjoy loved ones! Access to community indoor pool and seasonal outdoor pool Great perks like snowcone maker cottoncandy maker, axe throwing, ping pong, billiards, arcade game, Connect 4 and other games! Dog f

4.87 out of 5 average rating, 351 reviews

A wooden side table is adorned with a decorative tray holding candles and pebbles. Above, a framed artwork showcases a cityscape, while a wall clock displays the time. A framed certificate and a ceramic figure add character to the space.

Home in East Dubuque

Cozy Oasis/DBQ/FieldDreams/Galena-Fenced for Pets

As natives to Dubuque and Galena , we wanted a place we could come home to when visiting that is also PET friendly!! Plenty of indoor/outdoor space. Make this your FIELD of DREAMS home base - just 20 minute drive to field and then you are 2 miles from Dubuque Casino and 14 mile scenic drive to Galena Main Street.Outdoor patio with plenty of seating , fire pit for late night snacks w camping chairs, Grill for your outdoor cooking. We have it all and if we don’t we will find it!! Fenced backyard!

The aerial view captures a serene landscape with lush greenery and hills in the background. The townhome neighborhood is highlighted, surrounded by trees and well-maintained lawns, with a glimpse of a red barn in the distance. The scene conveys a peaceful natural setting.

4.98 out of 5 average rating, 165 reviews

Wooded Villa with Resort Access, Fireplace, K Bed

⭐King bed with plush bedding in a peaceful, private setting ⭐Wood-burning fireplace — perfect for cozy evenings together ⭐2-minute drive to the North Golf Course, driving range, & Stonedrift Spa ⭐Wooded nature views & tranquil surroundings for a relaxing escape ⭐Just 12 minutes to downtown Galena — excellent shopping, dining, & sight-seeing ⭐Access to Owner’s Club amenities including indoor pool & fitness center ⭐15 miles to Chestnut Mountain Skiing ⭐2 Full bathrooms & newer full size sofa bed

4.95 out of 5 average rating, 186 reviews

The spacious interior showcases an open floor plan with comfortable seating areas, a dining table, and large windows that provide views of the surrounding woods. The loft area can be seen above, enhancing the airy feel of the cottage.

Farm stay in Dubuque

Creekside Cottage farm stay nice for two to six.

Relax and enjoy time together at Creekside. The cottage is a picturesque spot for one or two guests or for groups up to 6. Extra guest charge is $20 per person after 2. Located on our farm only 15 minutes from downtown Dubuque and the Mississippi Riverfront. Explore the woods, fields, and creek on our farm. Visit the animals. A short drive to Mines of Spain, EB Lyons Nature Center, Eagle Point Park, Galena, Bellevue, Chestnut and Sundown ski areas, two monasteries, craft breweries, wineries.

4.98 out of 5 average rating, 166 reviews

A spacious living area features vaulted wood ceilings and a stone fireplace, creating a warm focal point. Cozy seating arrangements include plush sofas and armchairs, accompanied by decorative blankets. Large windows allow natural light to flood the space, showcasing wooded views outside.

Cabin in Galena

*Hot tub-Fire-3 king beds-Game room*Winter fun!*

Relax, unwind, & explore at this winter retreat in Galena Territory! Escape to this cozy, spacious cabin for a peaceful winter getaway. Sip morning coffee as snow falls through the trees, then unwind in the hot tub or by the fireplace. Roast marshmallows around the fire or enjoy arcade games, air hockey, darts, and more indoors. Stay active with access to the owner's club—indoor pool, fitness center, and pickleball (8 amenity cards included). Perfect for relaxation and winter adventure!

A warm living area features a brick fireplace with a mounted television above it. Large skylights and windows allow natural light to fill the space. A coffee table stands at the center, adorned with decorative items, complemented by comfortable seating and a vibrant area rug.

4.97 out of 5 average rating, 115 reviews

Secluded Treehouse, w/great views, close to Hwy 20

Enjoy the many charms of this one of a kind Tuscan style treehouse with different levels showcasing spectacular views. This home has every amenity and personal touch of home to make your stay relaxing and memorable. Conveniently located approximately 1 mile off Highway 20 in the Galena Territory, backing up to hole 13 on The General Golf Course. Set back off the main road you will enjoy privacy without sacrificing convenience and access to the many amenities offered during your stay.

A comfortable living area is featured with two spacious sofas and a round coffee table. A wall-mounted television is positioned above a stylish fireplace, with large windows showcasing views of grassy landscapes. Soft textiles and decorative art add a welcoming touch.

4.95 out of 5 average rating, 103 reviews

*King Bed*, *Fire Pit Table* & *Stunning Views*

Welcome to The Golf View, where relaxation and fun collide! This 1-bedroom, 2-bath abode is perfect for a romantic getaway or a golfing adventure with pals. Whip up a culinary masterpiece in the fully-equipped kitchen, chill out with some vintage tunes on the mezzanine loft, or binge-watch your favorite shows on the 50" Smart TV. Outside, unwind on the deck or get cozy around the fire pit table for some unforgettable nights. Book your stay now and get ready for a hole-in-one experience!

This historic brick home features multiple windows reflecting a classic architectural style. A stone garage, designed with modern doors, complements the house. Lush greenery surrounds the property, enhancing its natural appeal. A paved driveway leads to the garage, showcasing an inviting approach to the entrance.

4.95 out of 5 average rating, 231 reviews

1842 Bavarian Brew House

Nestled in charming and historic Galena this beautiful home was built in 1842 by brewer Peter Specht from Bavaria. The cellar operated as his brewery and tavern while living in the home above. The house was extensively renovated in 2008. It remains full of character and charm, but now boasts an abundance of modern comforts. A quiet private patio and yard are the perfect spot for a morning coffee or a glass of wine. All within a few walkable blocks to Main Street, the heart of Galena!

4.92 out of 5 average rating, 371 reviews

A blue A-frame house is showcased, surrounded by greenery. The brick walkway leads to a cedar deck, framed by landscaping. Windows are visible on the sides, allowing natural light to fill the interior.

Chalet in Elizabeth

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

The charming two-story miner's cottage features a welcoming front porch adorned with historic American flags. Lush greenery surrounds colorful flower beds, enhancing the outdoor space. The stone and white clapboard exterior reflects classic architectural elements within the Galena National Historic District.

4.96 out of 5 average rating, 580 reviews

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!

A spacious kitchen features a large island with four stools and sleek cabinetry. Modern stainless steel appliances are showcased, along with a stylish tile backsplash. Natural light streams in through a window, highlighting the open design that connects to the adjoining living area.