Vacation rentals in Galena

4.99 out of 5 average rating, 346 reviews

A rustic wooden light fixture hangs from the ceiling, featuring a long beam with attached pendant bulbs. The warm glow of the bulbs contrasts against the light-colored wall, while a decorative wall piece is visible below, enhancing the cozy ambiance of the space.

Guesthouse in Galena

The Guest House - Private and All Yours

*Some revenue from your stay will go to SPLC, ACLU, and other progressive causes* Enjoy the cozy comforts of this renovated studio in Galena's historic district. The building is yours for your stay, with driveway parking onsite. We've made this a welcoming space for respectful travelers of all backgrounds, so join us for a comfortable and unforgettable time in our beautiful and historic city. Our space is privately operated by us, not a rental company. We live onsite, and been here for 20 years.

A vintage clawfoot bathtub is positioned beneath a window adorned with floral curtains. A side table is visible, holding toiletries. The space features light-colored walls and elegant framed art, contributing to a classic bathroom ambiance.

4.97 out of 5 average rating, 115 reviews

Galena, Super Nice 1 BR, Loft Apartment

The 1842 Federal House offers this fully furnished & equipped 1 BR loft apartment, light filled living room, queen bedroom, private bath, full kitchen, private balcony w/ views of Galena. TV, high speed internet, all utilities paid. Fresh linens & towels weekly, free laundry in building. On site, off street parking. Outside relax on the front patio or the back garden. Excellent Bench Street location, next door to the Library & just steps from Galena's restaurants, shops, hiking & biking trails.

Superhost

A lively view of Main Street captures a bustling street scene filled with pedestrians and vintage cars. Historic buildings line both sides, showcasing brick facades and colorful awnings. People gather along the sidewalk, creating a vibrant atmosphere in this charming town.

Loft in Galena

4.85 out of 5 average rating, 534 reviews

Million Dollar View Main Street Galena

Hello there! This historic apartment has been completely renovated. It features exposed original brick, and hardwood floors. This room is equipped with a comfy queen bed, Roku TV with a variety of cable channels, and a kitchen (complete with an oven, stove, microwave, and fridge). Feel free to use any of them! Channel your inner cook! The bathroom features a shower and bath tub. This apartment is located above Big Bill's coffee shop and boasts incredible views of Galena's historic Main Street!

4.96 out of 5 average rating, 140 reviews

An inviting outdoor deck is shown, furnished with a dark sectional seating area and a gas grill. Soft lighting emits from a wall-mounted lamp, enhancing the cozy atmosphere. A backdrop of lush greenery and trees creates a serene setting, with a sunset sky adding warmth to the scene.

Tiny home in Galena

Romantic Tiny Home*Fireplace on deck*King bed*Cozy

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!

The historic J. G. Schmohl building is depicted, showcasing ornate architectural details and a façade painted in white. Large windows are framed elegantly, allowing natural light to fill the space. The image captures the grandeur of the building against a backdrop of blue sky with scattered clouds.

4.98 out of 5 average rating, 303 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.

A charming street scene captures a snow-covered downtown area at dusk. Brick buildings, including the Simply Elegant Boutique, are illuminated with warm light. A gentle slope is visible in the background, leading to a steeple that tops the hill, surrounded by falling snowflakes.

4.95 out of 5 average rating, 341 reviews

Downtown Gem for Two

Newly remodeled downtown apartment right in the middle of town. New furnishings, office nook with desk, full size kitchen and appliances, smart tv, free wifi, large open living space with private bedroom and bath. Very clean. Adjacent shared deck with table and chairs is available for use. This is a second floor apartment in the back of Simply Elegant Boutique so there are 17 steps to get to it from the outside. *Rest easy, every surface and door knob is disinfected after each stay.

5 out of 5 average rating, 149 reviews

A large river cruise ship is seen navigating along the Mississippi River. Lush green hills rise in the background, and the water is dotted with aquatic plants. The serene scene invites contemplation of the natural surroundings.

Home in Dubuque

Home by the River

Situated alongside the Mississippi River, wildlife abounds in every season. With eagles nesting nearby, there is always something new to see from the beautiful sunrises, cruise ships passing by, and watching the commerce of the barges and railroad right out the front window! This home has been recently refurbished and sits at the edge of our 15 acres. We have 2 dogs and welcome well-behaved pets. You can see us and visit with us if you like, or you can maintain privacy 10 acres away!

4.98 out of 5 average rating, 162 reviews

An indoor swimming pool is depicted, featuring a spacious area with clear water reflecting the high vaulted ceiling. Large windows provide natural light, while rows of seating line the sides. The pool includes marked lanes for swimming, creating a relaxing atmosphere.

Treehouse in Galena

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

A renovated bathroom features a natural wood countertop with a circular, dark-finished sink and a large mirror above. Soft, white towels are neatly arranged on the counter. Adjacent is a toilet and a safety grab bar aesthetically integrated into the design.

4.93 out of 5 average rating, 412 reviews

Johnson Apartment and 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, 348 reviews

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

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

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.

4.96 out of 5 average rating, 545 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!

A modern kitchen is showcased with dark cabinetry and patterned backsplash tiles. Soft lighting highlights the stainless steel appliances and wooden accents. Exposed brick walls add texture, while a clock is mounted on the wall near the entrance to a hallway.

4.97 out of 5 average rating, 101 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

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Villas

Luxurious estates for the ultimate escape

Houses

A space thats all yours, with room for everyone

Popular amenities for Galena vacation rentals

Self check-in

Monthly stays

Pet friendly

Laptop-friendly workspace

Gym

Ski-in/ski-out vacation rentals in Galena

4.99 out of 5 average rating, 296 reviews

A serene view of a tranquil pond reflects a cozy cabin surrounded by greenery. Soft grasses frame the foreground, while the sky showcases gentle clouds. The cabin features a covered porch, enhancing the peaceful ambiance of the quiet country location.

Cabin in Durango

Cozy Cabin by the Pond

A charming lodge-style building with a combination of brick and timber exteriors is framed by lush trees. The scene depicts a serene sky at dusk, enhancing the tranquil ambiance of the resort, with large windows reflecting the twilight hues.

Hotel room in Galena

Club Wyndham Galena IL

The exterior of the villa features a welcoming entrance with a decorative 'WELCOME' sign. A light dusting of snow covers the roof and front steps. The front porch is bordered by a small railing and has a cozy, inviting feel.

Unit has been sold and is no longer for rent

The bedroom features a spacious bed adorned with an assortment of decorative pillows and a soft throw blanket. Nightstands on either side are accompanied by lamps, providing gentle lighting. A small potted plant adds a touch of greenery to the inviting space.

4.8 out of 5 average rating, 5 reviews

Lakeview, newly renovated home

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House rentals in Galena

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.

4.96 out of 5 average rating, 284 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

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, 245 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

A bathroom space features a light green wall, complemented by wooden accents and a stained glass window providing natural light. A countertop is visible alongside vertical storage cabinets. A basket filled with neatly rolled towels is placed on the tiled floor.

4.94 out of 5 average rating, 174 reviews

Galena home close to Main St with parking and deck

5 out of 5 average rating, 139 reviews

Home in Dubuque

Welcome to the Hemmer House

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, 101 reviews

Perfect Location! Owner Club Access, Dog Friendly!

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, 201 reviews

Galena Getaway

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, 150 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.

4.97 out of 5 average rating, 147 reviews

Pools, Hot Tub, Fire tables, dog friendly

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Dog friendly vacation rentals in Galena

4.89 out of 5 average rating, 192 reviews

A wooden bed with a tall headboard and elegant posts is positioned in a well-lit room. Fluffy pillows rest atop a neatly arranged white comforter. A matching wooden dresser with multiple drawers sits nearby, featuring a mirror that reflects the room's warm hues.

Home in Dubuque

Historic+private brick loft by colleges & downtown

Superhost

A comfortable living area is presented with a dark sectional sofa, accompanied by a wooden coffee table. Natural light enters through large windows adorned with dark curtains, while a decorative clock and artwork add character to the space. A fireplace is also visible.

4.83 out of 5 average rating, 138 reviews

131 Plum Cove - 3 Beds, 3 Baths, Sleeps 8

4.94 out of 5 average rating, 163 reviews

A historic Gothic Revival house is seen with its original charm. Lush greenery surrounds the property, with a large yard and well-maintained gardens. A signpost is located at the intersection of two streets, indicating the house's position in a quiet residential area.

Cottage in Bellevue

Cute cottage, short stroll to Mississippi River!

4.98 out of 5 average rating, 364 reviews

A wooden swing hangs from a tree in a lush green field, gently swaying in the breeze. In the background, the log home is set atop a hill, showcasing its wrap-around deck and panoramic views of the surrounding landscape under a clear blue sky.

Guesthouse in Stockton

Highview Country Escape - Cozy Cabin with a view

4.92 out of 5 average rating, 127 reviews

An open living area showcases exposed brick walls illuminated by modern lighting. Two brown armchairs are positioned beside a side table, while a light gray sofa is accented by colorful cushions. Large windows allow ample natural light to fill the space.

Apartment in Dubuque

Modern Space on Main with On-Site Parking!

4.96 out of 5 average rating, 114 reviews

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.

Vacation home in Galena

Aspen House - A Private Quiet Getaway In Nature

4.98 out of 5 average rating, 113 reviews

Farmhouse Chic|Fireplace|View|Peloton|Near Town

A foosball table is placed in the foreground, featuring players in red and white uniforms. A cozy plaid armchair sits nearby, with a large television mounted on the wall displaying a nature scene. Natural light filters through the sliding glass doors, enhancing the space.