Family-friendly holiday rentals in Galena

A welcoming living area features a vaulted ceiling and large windows that provide views of the outdoors. A brick fireplace adds warmth, while comfortable seating is arranged around a coffee table. Soft lighting enhances the cozy atmosphere, complemented by decorative plants and artwork.

4.9 out of 5 average rating, 187 reviews

The Airy Aerie: Owners' Club access, golf nearby!

Welcome to the Airy Aerie: an avian themed townhome in the heart of the Galena Territory. Our space has been carefully curated to reflect the diversity of birds you will find in the natural surroundings of the area. There are two ensuite bedrooms and a full kitchen featuring granite countertops and stainless steel appliances. There is a loft space upstairs where a rollout twin bed can be set up. Our home can accommodate a maximum of 6 overnight guests (assuming 1 person on the twin rollout bed).

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.

4.98 out of 5 average rating, 326 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.

The image showcases a cozy bedroom featuring a king bed with white linens, a rustic brick wall, and modern nightstands. A spacious living area includes a leather sofa and stylish decor. A view of downtown with parked cars is visible from a window, emphasizing the prime location.

4.93 out of 5 average rating, 273 reviews

Suite Victory #1 On Main St w/ Reserved Parking

Suite Victory #1 (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. 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 island, quartz countertops, and new appliances. Stackable washer and dryer within the unit. MAX 2 PEOPLE. NO DOGS ALLOWED.

Treehouse in The Galena Territory

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.

4.98 out of 5 average rating, 189 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

4.87 out of 5 average rating, 821 reviews

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

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)

4.93 out of 5 average rating, 434 reviews

Johnson Apartment at Cathouse Suites, Dogs OK w/$$

Newly renovated building in historic, Uptown Galena above Miss Kitty's Grape Escape. Enjoy amazing views of downtown without having to take a single stair. Fully accessible apartment features lowest threshold shower, kitchenette with microwave and coffee/kcup maker, large rooms, 55" smart TV with wifi, bathrobes and lush towels. Living room includes very comfy sofa (but does not pull out). Easy access to premier night life and entertainment just below at Miss Kitty's Grape Escape.

4.92 out of 5 average rating, 364 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

Tiny home in The Galena Territory

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.

4.95 out of 5 average rating, 164 reviews

Cozy Romantic Getaway*Fireplace on deck*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!

4.96 out of 5 average rating, 570 reviews

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

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 round dining table is set outdoors with four yellow plates, each topped with a drink garnished with olives and celery. A bottle of cocktail mix rests beside the glasses, surrounded by textured placemats. Lush greenery provides a natural backdrop.

4.92 out of 5 average rating, 109 reviews

Perfect Location! Owner Club Access, Steps to Pool

Cozy Tranquility on Walnut, Galena IL Entire Home Vacation Rental, 1 Bed, 2 Bath, 4 Person Occupancy This adorable, recently remodeled and refurnished, 1 bedroom/2 full bath townhome is ready to welcome and embrace you any time of the year! Situated with seasonal views of the North Golf Course, and just a short distance from the driving range makes it a great choice for golfers... it's charm and central location make it an ideal choice for everyone!

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.

4.99 out of 5 average rating, 381 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.

5 out of 5 average rating, 200 reviews

The exterior of a revitalized 1950s car wash is showcased, featuring a curved awning and a large glass door. The building has a bright white facade with a red accent roof, and signage reading 'The Car Wash Inn' and '$1.25 WASH' is displayed.

Home in Shullsburg

The Car Wash Inn A Unique Stay

Enjoy a unique stay inside a beautifully revitalized single bay 1950s car wash. Only minutes away from historic downtown Shullsburg. This space has been thoughtfully designed to retain it's industrial charm with a nostalgic ambiance, while offering modern amenities for a comfortable stay. ~20 miles to Galena, IL ~25 miles to Mineral Point, WI ~25 miles to Dubuque, IA ~ATV Trail Access with large parking area

Popular amenities for Galena family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A charming gray house is set against a backdrop of colorful autumn foliage. The front porch features a red door, framed by shrubs and well-maintained landscaping. A clear blue sky provides a bright contrast to the warm tones of the trees.

4.97 out of 5 average rating, 303 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

A charming house is nestled among trees, with a gravel driveway leading to the entrance. The natural landscape features various shades of green, and the sky above is partly cloudy. The design of the house includes multiple windows and a welcoming front entry.

4.98 out of 5 average rating, 100 reviews

*New Kitchen*Screened Hot Tub*Owners Club*Dogs OK*

The exterior of a charming blue vacation rental showcases a welcoming front porch with seating. A stone pathway leads through landscaped areas with plants, approached by a warm sunset sky. The structure features multiple windows, allowing natural light to illuminate the inviting entryway.

4.97 out of 5 average rating, 104 reviews

Hot tub | 3BD|3BA en-suites | Resort Amenities

Holiday home in The Galena Territory

A spacious 7-seat hot tub is situated on the back patio, surrounded by lush greenery. The bubbling water and soft glow of market lights create a serene atmosphere, providing a perfect spot for relaxation amidst nature.

4.96 out of 5 average rating, 114 reviews

The Gathering Place- Modern, Spacious, 6 bedrooms

A spacious living area is highlighted by a large sectional sofa in warm tones. Natural light pours in through skylights, illuminating wooden floors. A dining table with multiple chairs is visible, alongside a well-equipped kitchen in the background, creating an inviting and open atmosphere.

4.9 out of 5 average rating, 138 reviews

Cozy Retreat | Hot Tub | Firepit | Dog-friendly

Superhost

The modern home is set against a backdrop of trees, with a flat grassy area in the foreground. The structure features large windows and a prominent stone chimney, offering ample outdoor seating on the deck. The natural surroundings create a peaceful atmosphere.

4.89 out of 5 average rating, 126 reviews

Modern Home w/Amazing Views, Hot Tub, Game Room

The exterior of a spacious home is displayed, featuring a wraparound deck and large windows that allow ample natural light. Outdoor seating options, including blue chairs and a stone fire pit, are positioned on a grassy area surrounded by mature trees.

4.94 out of 5 average rating, 168 reviews

Awesome Lodge in Galena Territory

An outdoor deck features comfortable seating arrangements, including wicker chairs and a coffee table. Large windows in the background allow natural light to fill the adjacent indoor area while showcasing the surrounding greenery.

4.98 out of 5 average rating, 171 reviews

*Holiday Getaway! Fireplace, Hot Tub, Fire Tables*

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 225 reviews

An outdoor seating area is presented with a round table surrounded by six wrought iron chairs. A potted plant adds a touch of color to the table, while flowers are visible in the flower beds nearby. Large windows on the house allow natural light to enter.

Townhouse in Bellevue

Pet friendly, 2 BR close to Mississippi River

A tranquil vacation home is set in a lush green landscape. The house features a screened-in porch and multiple balconies, surrounded by a wooden fence. Mature trees provide shade, and the inviting lawn enhances the serene outdoor environment.

4.93 out of 5 average rating, 214 reviews

Galena Getaway

4.87 out of 5 average rating, 204 reviews

The exterior of a two-story building is shown, featuring a combination of brick and siding. A covered porch with hanging flower pots invites relaxation. Lush greenery surrounds the entrance, and a sign indicating the property name is visible. Parking is available in the vicinity.

Home in Downtown Dubuque

The Dubuque House - Historic Downtown Location!

4.8 out of 5 average rating, 123 reviews

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

Mississippi River house has everything you need

4.9 out of 5 average rating, 225 reviews

The kitchen features wooden cabinetry with ample storage space and stainless steel appliances. A granite countertop provides a functional workspace, and a decorative backsplash enhances the room's design. Natural light is accessible through a nearby window, accentuating the warm wood tones.

Flat in Dubuque

Impressive Private 2BR Suite w/Parking Univ. Area

A charming exterior view of the house is showcased, featuring a welcoming front porch with white railings and two rocking chairs. Lush greenery surrounds the home, and a stone pathway leads to the entrance. Sunlight filters through the trees, casting gentle shadows on the lawn.

4.95 out of 5 average rating, 152 reviews

Family-Friendly Wooded Retreat- 3 Ensuite Bedrooms

Holiday home in The Galena Territory

A charming red cottage is nestled among tall aspen trees. A winding stone pathway leads to the entrance, which features a wooden door and large window. Lush greenery surrounds the house, enhancing the tranquil forest setting.

4.95 out of 5 average rating, 128 reviews

Aspen House - A Secluded Getaway In Nature

The living area features a comfortable sofa and a rustic coffee table atop a circular rug. A stone fireplace serves as a focal point, complemented by a vibrant artwork of a rooster above it. Natural light floods in through large windows, providing views of the outdoor patio.

4.98 out of 5 average rating, 127 reviews

Farmhouse Chic|Fireplace|View|Peloton|Near Town

Family-friendly home rentals with a pool

A gravel fire pit area is positioned in the foreground, surrounded by a circular stone border. The spacious yard is framed by trees, providing a natural setting. In the background, a cozy wooden house with a deck is partially visible, blending harmoniously into the landscape.

4.95 out of 5 average rating, 257 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

5 out of 5 average rating, 30 reviews

12pmCheckIn |KiwiDen 4 KIDSl A&D Rise Getaways

An open living space features a modern kitchen with stainless steel appliances and a spacious island. A staircase with wooden railings leads to a second-level area illuminated by large windows. The dining area includes a long table and comfortable chairs, creating an inviting atmosphere.

4.92 out of 5 average rating, 64 reviews

Cozy retreat in Galena Territory

Cottage in The Galena Territory

A charming two-story cottage features blue siding and a decorative front door, framed by small windows on either side. A front pathway, bordered by greenery, leads to the entrance, while a lamp post stands nearby, illuminating the welcoming exterior.

4.98 out of 5 average rating, 60 reviews

Storybook Countryside Cottage

An open living area showcases a bright red sofa with decorative pillows, positioned next to a glass-top coffee table. The wooden staircase leads to an upper level with a railing, while large windows invite natural light and offer views of the surrounding greenery.

4.82 out of 5 average rating, 76 reviews

House 3bd/3bth- indoor pool -close to chestnut mnt

The exterior of a well-maintained townhome is showcased, featuring a welcoming entryway with a small porch. A stone walkway leads through landscaped grass, bordered by various plants. A light fixture stands on the pathway, and the overall setting is surrounded by greenery and trees.

5 out of 5 average rating, 85 reviews

Serene 2 King Bd Villa, Fireplace, Near Spa & Ski

The open-concept living area showcases a cozy couch accented by a decorative rug. A mounted television is positioned on a wooden feature wall. A dining table is visible in the background, accompanied by modern kitchen amenities and large windows that allow natural light to illuminate the space.

4.96 out of 5 average rating, 114 reviews

Hook Wine And Sinker - Golf, Shop, Pools, & Relax

A modern mid-century home with a grey exterior sits amid lush greenery. Steps lead to a welcoming front door, framed by large windows and angular architectural details. Pathways lined with flowering shrubs provide an inviting approach to the property.