Holiday rentals in Jo Daviess County

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Top-rated holiday rentals in Jo Daviess County

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Guest favourite
A charming cabin exterior is framed by a white picket fence adorned with colorful flowerbeds. The house features a sloped roof and warm wood siding, with lights illuminating the inviting entrance. Lush greenery surrounds the property, enhancing the tranquil outdoor setting.
Tiny home in Galena
4.93 out of 5 average rating, 182 reviews

Hygge nature retreat-propane fire pit-King bed

Enjoy the cozy setting of this romantic nature retreat at The Hygge Haus. Hygge ("hooga") is about taking time away from the daily rush to be together with people you care about - or even yourself - to relax and enjoy life's quieter pleasures. Come hygge in our cozy house meant for two, wrap in a fuzzy blanket by a fire. Feel contentment in sharing a cozy meal at the table, sitting by a fire on the deck, enjoying the outdoors. Relax, unwind, & explore the Galena Territory and nature. Cozy up!

Guest favourite
A tri-level house with a muted gray exterior features multiple large windows. A front porch with railings is visible, inviting relaxation. Surrounding greenery and a neatly maintained yard contribute to the peaceful setting. The sloped roof adds character to the home.
Home in Galena
4.92 out of 5 average rating, 101 reviews

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.

Top guest favourite
The A-frame cabin, framed by trees, features a striking black exterior with warm wood accents. A large front window provides natural light, while a festive wreath adorns the entrance. Surrounding greenery adds to the serene atmosphere of the countryside setting.
Cabin in Elizabeth
4.97 out of 5 average rating, 102 reviews

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.

Guest favourite
The modern living space features a grey sofa with a patterned throw pillow, positioned near a wooden coffee table. A dining area with two black chairs is visible, alongside an open kitchen that includes stainless steel appliances and dark cabinetry. Natural light brightens the room.
Flat in Galena
4.99 out of 5 average rating, 158 reviews

Ulysses Suites, Suite 302

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 as a nod to its previous existence as the Grant Hotel from 1895 to 1933. Suite 302 is an ADA accessible unit located on the 3rd floor and can be attached to Suite 301.

Top guest favourite
The living area features mid-century modern furniture with vibrant green and orange chairs surrounding a coffee table. A gas fireplace is centered under a unique light fixture, and large windows allow views of the surrounding woods. A dining area is visible in the background.
Treehouse in Galena
4.99 out of 5 average rating, 212 reviews

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

Top guest favourite
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.
Home in Galena
4.95 out of 5 average rating, 235 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!

Top guest favourite
An open interior space features a spacious bed with neutral bedding and a cozy throw. A modern kitchenette, equipped with essential appliances, is visible. A jetted tub sits beside a decorative wall, while large windows offer views of the water and bring in natural light.
Place to stay in East Dubuque
4.96 out of 5 average rating, 298 reviews

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.

Top guest favourite
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
4.92 out of 5 average rating, 373 reviews

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

Guest favourite
An inviting living space features an exposed brick wall and hardwood flooring. A spacious bed with a colorful quilt is positioned next to a flat-screen TV. A comfy couch and a unique wooden coffee table complete the area, with soft lighting provided by two floor lamps.
Loft in Galena
4.82 out of 5 average rating, 874 reviews

Rustic Apartment Main Street Galena

Welcome to our cozy apartment located inside Galena’s historic Logan House Hotel building. Conveniently located on the north end of Main St(above Big Bill’s coffee shop), this fully-renovated unit features exposed original brick, and hardwood floors. Equipped with a cozy electric fireplace, mounted Roku TV, comfortable couch, and kitchen, this apartment is warm and inviting! Check out all our listings at Airbnb.com/p/galenaapartments ( copy & paste into URL)

Guest favourite
Cabin in Galena
4.89 out of 5 average rating, 104 reviews

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.

Guest favourite
A charming tiny home, crafted from natural wood, stands conveniently on wheels. A picnic table occupies the grassy area in front, with outdoor seating to the side. Windows framed with shutters offer views of the surrounding landscape, including the nearby river.
Tiny home in Bellevue
4.95 out of 5 average rating, 107 reviews

The Shady Haven (Tiny Home 1)

Have you ever wanted to stay in a Tiny Home but haven't had the opportunity? Now you can stay in a custom built Tiny Home right along the mighty Mississippi River in Bellevue Iowa! These Tiny Log Cabin Homes feature all the comforts of a standard home including Heat/AC, Kitchen, Bathroom, living room and sleeping loft. Each Tiny Home sleeps 4 adults with a queen bed in the loft and a pull out sofa in the living room. Outside is a private picnic area.

Top guest favourite
A decorative sign reading 'Dawson's Remise' is illuminated in warm tones, framed in black wood. Next to it is a textured pillow featuring a geometric red and black pattern, adding a modern touch to the setting.
Flat in Galena
4.99 out of 5 average rating, 394 reviews

Dawson's Remise Luxury Accommodation

Enjoy a luxurious stay in our remise ("carriage house"), complete with authentic Art Deco and Industrial furniture and design. We took great care in ensuring top notch craftsmanship and amenities, so as to create an inviting environment that you won't want to leave! Hidden away off the quaint and historic Park Avenue, you'll enjoy a quiet and restful stay whilst within walking distance to Main Street Galena and all it has to offer.

Popular amenities for Jo Daviess County holiday rentals