Holiday houses in Jo Daviess County

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Top-rated holiday rentals in Jo Daviess County

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Guest favourite
The living area features a comfortable sofa, accented with pillows, and a pair of ottomans. Two windows allow natural light to fill the space, adorned with sheer red curtains. A television is positioned on a wooden stand, accompanied by decorative plants and framed artwork.
Home in Bellevue
4.8 out of 5 average rating, 125 reviews

Mississippi River house has everything you need

Your family will be close to everything when you stay at this centrally-located place. The river is right across the street and so is the walkway the walkway will take you all the way to the other end of town beautiful walk along the river. Richmond‘s café Great place for breakfast. The brewery has igloos to sit in outside just two blocks from the guest house. The river park will be lighted for Christmas right across the street all the way through the end of town Great place to be this holiday

Guest favourite
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
4.95 out of 5 average rating, 186 reviews

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.

Guest favourite
Townhouse in Galena
4.95 out of 5 average rating, 131 reviews

Quiet getaway with wooded views

Welcome to Scenic Serenity, a charming golf villa in The Galena Territory, surrounded by peaceful wooded views. ✔ Main Level (Lower Level): Features vaulted ceilings, a cozy seasonal fireplace (Oct-February 28), two skylights, and an open-concept layout. Enjoy a roomy eat-at bar, a bedroom with full bath access, and a sleeper sofa in the living area. ✔ Upper Level: Overlooks the living and dining rooms, offering a spacious bedroom with a private bath and a utility closet with a washer/dryer.

Top Guest favourite
The spacious bedroom features a king bed with grey bedding, complemented by a rustic accent wall and a ceiling fan. A window provides a view of downtown Main Street. The living area showcases a comfortable seating arrangement with a patterned rug and brick accents.
Apartment in Galena
4.98 out of 5 average rating, 411 reviews

Suite Victory #2 On Main St w/Reserved Parking

Suite Victory #2 (facing Main St.) Beautifully renovated apartment on Main St. right where you want to be with Reserved Parking. Dining, entertainment, and shopping just outside your door. Large open floor plan with beautiful views of downtown on the corner of Main Street and the old cobbled Perry Street. King bed. Double sink vanity and large walk-in shower. Kitchen has oversized island, quartz countertops, and new appliances. Full size washer and dryer within unit. MAX 2 PEOPLE. NO DOGS.

Top Guest favourite
A bright bedroom features a spacious bed covered with a dark throw blanket. A large window seat, adorned with cushions, offers views of the street. A small table and chair sit nearby, with hardwood flooring and elegant decor enhancing the room's character.
Apartment in Galena
4.98 out of 5 average rating, 334 reviews

Ulysses Suites, Suite 202

Ulysses Suites has just been completed inside the historic J. G. Schmohl building in the heart of downtown Galena, located at 213-217 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 202 is a gorgeous studio with a huge window seat looking over Main Street.

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, 206 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
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, 293 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, 372 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
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, 179 reviews

Hygge Romantic Getaway-Electric Fireplace-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, talking on the chaise built for two. Relax, unwind, & explore the Galena Territory and nature. Cozy up!

Guest favourite
Cabin in Galena
4.89 out of 5 average rating, 103 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.

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.
Apartment 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.

Guest favourite
Holiday home in Galena
4.95 out of 5 average rating, 136 reviews

Aspen House - A Secluded Getaway In Nature

Relax with your loved ones at the peaceful Aspen House. A Miner's Cottage nestled in a beautiful stand of aspen trees = a quiet retreat just for you! The property is surrounded by protected wooded green space with the Taylor Run trail adjacent on the northwest side. The Owners Club, pools & lake are accessible by hiking/ 5 minute drive. Enjoy bird watching, fishing, hiking and picnicking without driving anywhere!

Popular amenities for Jo Daviess County holiday rentals