Vacation rentals in Jo Daviess County

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Top-rated vacation rentals in Jo Daviess County

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Guest favorite

The exterior of a brick building is shown, featuring large windows adorned with planters. The ground floor includes storefronts with awnings, while the upper floor has a balcony with decorative railing. An American flag hangs at the entrance, emphasizing the historic charm of the location.

Loft in Galena

4.82 out of 5 average rating, 632 reviews

Fireplace Apartment Main Street Galena

My apartment is located right on Galena's historic main street also known as the Helluvahalfmile. The apartment has just been renovated though it is on the original listing for the apartment. It is now much better than before! There are restaurants and dining, family-friendly activities, and nightlife just feet away. You’ll love my place because of it's location, the ambiance, people and the Galena main street life. You are right above my restaurant too, which serves coffee, breakfast and lunch!

Top guest favorite

Villa in Galena

4.98 out of 5 average rating, 133 reviews

King Bd, Well-located Near Pool, Spa, Golf, Trails

✓Semi-private outdoor pool, steps away ✓Lake access ✓Well equipped kitchen w/modern appliances ✓Smart TV on each level w/Roku & YouTube TV ✓Computer desk ✓Fireplace w/supply of firewood ✓Queen sofa bed ✓2 Full baths ✓Gas grill ✓Indoor pool ✓Near hiking trails & paved walking trails ✓North Course & Driving Range, 2 min drive ✓Owner's Club access ✓Stonedrift Spa, 3 min drive ✓Downtown Galena, 15 min drive ✓Chestnut Mountain (Ski & Zipline), 25 min drive ✓Guest favorites: "cleanliness & comfort"

Top guest favorite

A bright corner space is showcased with large sliding glass doors allowing natural light to flow in. A single armchair is positioned nearby, with wooden flooring enhancing the room's warmth. Wall art with motivational phrases is displayed, contributing to a serene environment.

Townhouse in Bellevue

4.93 out of 5 average rating, 206 reviews

Pet friendly, 2 BR close to Mississippi River

This comfortable home is a 2 BR 1 BA with a full kitchen, and off street parking. It is 1 block away from the Mississippi River and within walking distance to local shops, restaurants bars, parks, and walking trails. The local grocery store is located directly across the street. Well behaved pets are welcome. The backyard is completely fenced in. NO SMOKING INSIDE. As stated in the other notes section, we are located along the Canadian Pacific Railroad and there will be trains going by.

Top guest favorite

A stone firepit surrounded by wooden benches is situated amid lush greenery. The octagon-shaped house is visible in the background, featuring floor-to-ceiling windows that reflect the surrounding woods. The private hot tub is positioned on the deck, enhancing the outdoor experience.

Treehouse in Galena

4.98 out of 5 average rating, 157 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

A clear sign stands in a grassy field, marked 'Springside Cabin Parking'. The sign is mounted on a metal post, with a decorative base featuring a colorful stone. Natural surroundings with distant wooded areas are visible in the background.

Tiny home in Dubuque

4.95 out of 5 average rating, 181 reviews

Off-grid Tiny House farm stay

The perfect place for 1-2 guests to unplug and relax in this beautiful, natural setting. It's a short distance (less than 2 min. walk) from the parking area to this quiet, private, 12'x14' one-room cedar cabin set on a pasture with picture-window view of wooded bluffs and stream, birds and other wildlife. Writing table and chair, glider rocker, woodstove, and gas cookstove. Solar-powered desk lamp. Port-a-potty and solar shower outside (summer only). Fire pit and outdoor seating.

Guest favorite

Home in Galena

4.95 out of 5 average rating, 242 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

Welcome to the Toasted Marshmallow; your cozy escape from reality. Enjoy the peace and quiet of this charming three bedroom, two bath home in The Galena Territories. Kitchen is fully equipped to meet your needs. Enjoy the additional lower level family room w/ 2nd fireplace so your group may spread out. Deck with ample room for dining outside and enjoying your coffee or wine. Home includes six access passes to the GTA Owner's Club and pools. Strong Wi-Fi for remote work, if needed.

Top guest favorite

The image captures the elegant façade of the J. G. Schmohl building, showcasing intricate architectural details and large windows. The white exterior contrasts with the blue sky above, highlighting the building's historic character and craftsmanship.

Apartment in Galena

5 out of 5 average rating, 117 reviews

Ulysses Suites, Suite 203

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 203 is almost 1400 square feet and is located on the 2nd floor.

Top guest favorite

An A-frame structure is surrounded by lush greenery, showcasing a large wooden deck that wraps around the house. Windows display a cozy interior, while the sloped roofline contributes to the house's unique design. Sunlight filters through the trees, creating a serene atmosphere.

Chalet in Elizabeth

4.92 out of 5 average rating, 344 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 entryway features a stone accent wall, complemented by a large mirror above a decorative fireplace. A wooden desk with chairs is positioned near the fireplace, and a staircase with patterned carpet leads to the upper level. Natural light illuminates the tiled floor.

Home in Galena

4.96 out of 5 average rating, 541 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

The exterior of the cabin is framed by trees, with warm lights glowing from within. A covered entrance leads to the front porch, which features wooden steps and stone accents. Fallen leaves cover the ground, enhancing the rustic appeal against a dramatic sunset sky.

Cabin in Galena

4.98 out of 5 average rating, 113 reviews

Family Time! Hot Tub•Fire Pit•Game Room•3 Kings!

Ultimate Family Escape in Galena Territory! Unwind, explore, and make memories at this chic, spacious cabin! Sip coffee on the deck as deer wander by, soak in the hot tub, and gather around the fire pit for s’mores. Stay cozy by the wood fireplace or challenge the family with arcade games, air hockey, pinball, and darts! Enjoy Owner’s Club access with a pool, fitness center & pickleball (8 amenity cards). Adventure awaits—book your perfect getaway today!

Guest favorite

A cascading waterfall flows gracefully over a rocky ledge, surrounded by lush greenery and trees. The water creates a serene scene as it descends into a calm body of water below, reflecting the clear blue sky above.

Townhouse in Galena

4.9 out of 5 average rating, 115 reviews

Spring Creek Sanctuary

Come enjoy nature's splendor at the "Spring Creek Sanctuary", a modern condo located in the Galena Territories. Our two spacious bedrooms & two bathrooms allow for groups or families to stay in comfort and style. All can congregate in the shared spaces to enjoy a well stocked kitchen, cozy living room with a wood burning fireplace and the deck area with it's beautiful views. Be sure to check out the amenities included with your stay!

Guest favorite

A serene waterfall cascades over rugged, dark rock formations into a tranquil green pool. The surrounding landscape features scattered trees and a gentle slope, with autumn foliage adding warm tones to the scene. The water flows effortlessly, creating a peaceful ambiance.

Townhouse in Galena

4.96 out of 5 average rating, 142 reviews

Contemporary Country Villa with Golf Course View

COMPLETELY UPDATED!!! 1 BR/ 2BA golf villa on the 10th hole. Upstairs in the unit features the bedroom with a queen-sized bed with memory foam mattress, and an adjacent full bath, and washer/dryer. Downstairs is the living room with wood-burning fireplace, slider to deck overlooking the 150-yard marker, kitchen and another full bath. Smart TVs for you to log into your streaming services (AmazonPrime, no cable.)