Vacation rentals in Jo Daviess County

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Top-rated vacation rentals in Jo Daviess County

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Top guest favorite

A custom log cabin is framed by lush greenery and manicured landscaping. The warm wooden exterior features multiple gabled roofs and large windows. A stone pathway leads through the vibrant garden, creating an inviting approach to the entrance.

Cabin in Galena

4.95 out of 5 average rating, 110 reviews

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.

Top guest favorite

Villa in Galena

4.98 out of 5 average rating, 148 reviews

Cute&Cozy Golf Villa, King bd, Fireplace, Near Spa

✓Peaceful, nature views w/ wooded backdrop ✓Lovely fall colors ✓Great location ✓Well equipped kitchen w/modern appliances ✓Gas grill on deck ✓Smart TV on each level ✓Computer workstation ✓Fireplace w/supply of firewood ✓Near hiking trails & paved walking trails ✓Stonedrift Spa, 3 min drive ✓North Course & Driving Range, 2 min drive ✓Near downtown Galena, 15 min drive ✓Owner's Club access ✓Indoor pool ✓Lake access ✓Chestnut Mountain (Ski & Zipline), 25 min drive ✓20% discount ➡️ 7+ nights

Guest favorite

The living room showcases a bright orange sofa paired with a modern coffee table, amidst natural wood accents and greenery outside. A large television is mounted against a backdrop of floor-to-ceiling windows, providing ample light. Colorful wall art adds a playful touch to the space.

Treehouse in Galena

4.98 out of 5 average rating, 176 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 favorite

An outdoor fire pit is surrounded by several black Adirondack chairs, set among fallen leaves. The cabin is visible in the background, illuminated by warm lights, creating a cozy ambiance. Tall trees frame the scene, providing a sense of seclusion.

Cabin in Galena

4.98 out of 5 average rating, 137 reviews

*Winter Fun* *Hot tub-Fire-3 king beds-Game room*

Relax, unwind, & explore at this fall retreat in Galena Territory! Escape to this cozy, spacious cabin for a peaceful fall 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 pit 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 fall adventure!

Top guest favorite

An open living space showcases exposed brick walls and dark wood flooring. A round wooden dining table with four chairs is positioned adjacent to a cozy black armchair and ottoman. The kitchen area includes a refrigerator and cabinets, with a warm light illuminating the room.

Loft in Galena

4.87 out of 5 average rating, 800 reviews

The Brick Apartment Main Street Galena

Hello! Welcome to our beautifully-renovated apartment, conveniently located on the north end of Galena’s historic Main Street. This unit is above Big Bill’s coffee shop, and boasts exposed original brick from the historic Logan House Hotel, hardwood floors, a kitchen (range, refrigerator, microwave, sink), and beautiful views of our historic town! Only feet from restaurants, shopping, and night life! Check out all our listings at Airbnb.com/p/galenaapartments ( copy & paste into URL)

Top guest favorite

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, 359 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

Top guest favorite

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.

Home in Galena

4.96 out of 5 average rating, 563 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!

Top guest favorite

A modern living area features a cozy seating arrangement with two armchairs and a plush sofa. A decorative rug lies beneath a coffee table, while a television is mounted above a fireplace. Large windows provide natural light, complemented by artwork on the walls.

Apartment in Galena

5 out of 5 average rating, 134 reviews

Ulysses Suites, Suite 303

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. The Presidential Suite 303 is located on the 3rd floor.

Guest favorite

A comfortable seating area features two black reclining chairs with plush pillows, set against a backdrop of exposed brick walls and modern lighting. A glimpse of the outdoor street is seen from nearby windows, enhancing the vibrant urban atmosphere.

Apartment in Galena

4.97 out of 5 average rating, 118 reviews

Suite Victory #4 On Main St w/Reserved Parking

Suite Victory #4- 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.

Top guest favorite

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.

Apartment in Galena

4.99 out of 5 average rating, 373 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.

Guest favorite

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.

Home in Galena

4.96 out of 5 average rating, 102 reviews

Hot Tub + Fall Views | Peaceful Escape

Welcome to Pine Ridge—a peaceful, modern 2-bedroom, 2.5-bath vacation rental in The Galena Territory. With two king suites, a cozy living area, forest views, and a private hot tub, it’s perfect for couples, friends, or a remote work getaway. Relax on the porch, unwind by the fireplace, or explore nearby trails, shops, and GTA amenities. Just 5 minutes to the Owners Club and 10 minutes to downtown Galena.

Top guest favorite

An ornate rusted sign reads 'Welcome to the Ranch,' suspended among tall evergreen trees. The clear blue sky serves as a backdrop, enhancing the welcoming impression of the entrance to the property.

Guesthouse in Galena

5 out of 5 average rating, 306 reviews

Tree Tops

So much more than just a place to sleep! Tucked away in a cedar forest and built on stilts reaching the tree-tops, this eco-friendly, African-inspired lodging experience is one of a kind. Located on the owner's ranch in the rolling hills 12 minutes from downtown Galena, you feel as though you are nestled in the heart of nature. Horses, alpacas, and mini donkeys roam the secluded 37 acre property.