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Vacation rentals in Galena

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Popular amenities for Galena vacation rentals

Stay near Galena's top sights

Fried Green Tomatoes30 locals recommend
Otto's Place24 locals recommend
Log Cabin29 locals recommend
Blaum Bros. Distilling Co.14 locals recommend
Galena River Wine & Cheese3 locals recommend
Fritz & Frites Bistro11 locals recommend

Dog friendly vacation rentals in Galena

Guest favorite
The interior space is adorned with the Miss Kitty's Calhouse Suites logo, prominently featured at the forefront. A modern kitchenette and cozy living area are visible in the background, showcasing the welcoming design of the newly renovated apartment.
Apartment in Galena
4.93 out of 5 average rating, 403 reviews

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

JennRating, 5 stars2 weeks ago
This was our first trip to Galena. Loved staying downtown where we could walk to coffee shops, restaurants, bars, and stores. The accommodations had a creative and whimsical vibe and were just as described, easy to access, and clean. Just what we were looking for.
Guest favorite
An upper-level porch features a mix of seating options, including two rocking chairs and a glider, alongside a small coffee table. A telescope rests nearby, and the space offers views of the surrounding landscape, complemented by a wooden railing and overhead ceiling fan.
Home in Galena
4.93 out of 5 average rating, 196 reviews

Galena Getaway

RebeccaRating, 5 stars4 months ago
Stayed here with family. Easy to find. Quiet. Layout worked out well. 3 bathrooms! Able to block off stairs. traveled with a senior dog with a bad knee. Kitchen had anything we needed. Relaxing after a day at Chesnut Mountain. Beds comfortable, bathrooms spotless. husband enjoyed the puzzle ball game. Nicely decorated to reflect the holiday season!
Superhost
The living room features two comfortable seating options, including a brown recliner and a dark sofa with decorative cushions. A wooden coffee table is situated on an intricate area rug, while natural light filters through sheer curtains along the large windows. A clock is mounted on the wall.
Home in Dubuque
4.91 out of 5 average rating, 102 reviews

Historic Home with Pool Table and Dart Board

CrystalRating, 5 stars3 weeks ago
Jessica was very friendly. She gave upfront, easy instructions. The house was clean and easy to access. The description was perfect. We came for a weekend at UD. This house did not disappoint. Would definitely stay again!
Guest favorite
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.
Home in Galena
4.89 out of 5 average rating, 125 reviews

Cozy Retreat | Hot Tub | Firepit | Dog-friendly

NicoletteRating, 5 stars2 months ago
Family ski trip! It was perfect! 20min to Chestnut Ski resort and 15mins to downtown Galena! It was the perfect stay and plenty big enough. We will be back next year!
Guest favorite
A tranquil riverfront scene is presented, featuring a lush green lawn that meets the water's edge. A large tree offers shade, while a picnic area with seating is visible in the distance, inviting relaxation in nature.
Tiny home in Bellevue
4.95 out of 5 average rating, 101 reviews

The Shady Haven (Tiny Home 1)

JenniferRating, 5 stars3 weeks ago
I've always wanted to stay in a tiny house and I couldn't have picked a better one to try. Loved the location, the cabin had everything I needed for a short stay, and Dan and his wife are extraordinary hosts! You won't be disappointed. And I can't wait to see the Mill when that's finished and open.
Top guest favorite
A field of wildflowers, predominantly purple echinacea, is framed by tall grasses and illuminated by soft sunlight. In the background, a cabin is partially visible among the blooms, enhancing the natural scenery.
Guesthouse in Stockton
4.98 out of 5 average rating, 361 reviews

Highview Country Escape - Cozy Cabin with a view

GenyaRating, 5 stars3 weeks ago
What an incredible stay we had! The cabin is spotlessly clean and beautifully decorated with a warm and cozy vibe. The hosts thought of everything that could possibly be needed and were extremely responsive and helpful with anything we asked. The surrounding land is an oasis of peace and relaxation with so many spots to check out. We loved winding down in the hot tub and checking out the farm animals down the road. The pond is another amazing spot! All in all, we highly recommend this airbnb and we really hope we can come again.
Guest favorite
A charming exterior of a single-story home is shown, featuring a covered porch with railing. Snow blankets the ground, while bare trees frame the scene, highlighting the house's warm beige siding and large windows that invite natural light.
Home in Galena
4.94 out of 5 average rating, 130 reviews

Galena Cabin, Access to Owners Club, Privacy

NijikaRating, 5 stars1 month ago
We loved the home, and enjoyed our peaceful time there. The patio was great!
Guest favorite
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
4.96 out of 5 average rating, 106 reviews

Aspen House - A Private Quiet Getaway In Nature

JenniferRating, 5 stars1 month ago
Hailey was an excellent host. The Aspen House is beautiful. It was the perfect size for our family of 6. It has everything you could need. We really liked that there were plenty of blankets and entertainment outlets. Our youngest was excited to see that one of her favorite spiral toys was there. We had to leave abruptly in the wee hours of the morning due to a sick kid and Hailey made check out a breeze. We were grateful as she ended up being pretty sick. We will definitely look to stay here again when we're in the area.

House rentals in Galena

Guest favorite
A historic brick home is pictured from the front yard, featuring a peaked roof and white columns on the porch. Neatly trimmed hedges and a manicured lawn enhance the inviting exterior, while landscaped gardens with young trees are visible in the foreground.
Home in Dubuque
4.89 out of 5 average rating, 181 reviews

Cozy private brick loft by downtown-free parking

AprilRating, 5 stars1 day ago
We absolutely loved our stay. The place was beautiful and exactly as described. Very clean too!!! We loved the binder with information in it and reading all of the facts about the place. Great stay!!!
Top guest favorite
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
5 out of 5 average rating, 158 reviews

The Car Wash Inn A Unique Stay

ElizabethRating, 5 stars1 week ago
Our stay at the Carwash Inn was lovely!! The space is cozy and was perfect for our needs. The whole place was very clean and the bed was very comfortable, would recommend!
Top guest favorite
A spacious dining area showcases a large wooden table surrounded by eight chairs, with decorative placemats neatly arranged. Natural light enters through multiple windows, accented by burgundy drapes. A cozy living room is visible through the adjoining doorway, featuring comfortable seating and ceiling fan.
Home in Galena
4.94 out of 5 average rating, 170 reviews

Galena home close to Main St with parking and deck

ChristaRating, 5 stars3 weeks ago
Super cute place! Having the 4 bedrooms was great for our small group of girls. The dining and living room had the right amount of seating. We didn’t have to hop in the car to explore town. All the restaurants and shops were within walking distance but the location was on a side street so it felt private. I definitely recommend Deb’s place!
Superhost
A spacious brick home is surrounded by lush green landscaping and tall trees. The structure features multiple gabled roofs and a combination of large windows, providing natural light to the interior. A well-maintained lawn stretches across the front, inviting outdoor activities.
Home in Dubuque
4.89 out of 5 average rating, 177 reviews

Modern/Historic Mansion

JessRating, 5 stars4 months ago
Everything was great!
Guest favorite
The entrance features a spacious covered porch with four black wicker chairs arranged around a small table. Decorative planters with flowers are positioned at the edges, while a pathway leads to the main door, framed by the building's classic brick facade.
Home in Galena
4.97 out of 5 average rating, 136 reviews

Galena RowHouse - Downtown with parking included!

DebRating, 5 stars1 week ago
From making the reservation through check out Mary was great to work with. The property is just as described and a wonderful accommodation for a bachelorette gathering of 9+1 infant. The house was well furnished with comfortable beds and lots of extras that made our stay extra special. Having private parking was a big plus. The house is within walking distance of restaurants and shopping. Our group loved the private porch area for gathering. We never ran out of things to do! We highly recommend the Rowhouse and Galena for a fun weekend getaway.
Guest favorite
A living area is showcased with hardwood flooring, featuring a spacious sofa and two patterned armchairs. A coffee table is positioned centrally, surrounded by two end tables. Natural light is welcomed through large windows, complemented by decorative wall art.
Home in Galena
4.99 out of 5 average rating, 191 reviews

The Downtown House - 1820s home steps from Main St

RobertRating, 5 stars4 months ago
Awesome find a block from Main Street in downtown Galena, we’ve stayed here several times and are constantly impressed. Lauren has done a great job taking an older place and making it modern without removing the charm. Everything from Bluetooth speakers to a modern kitchen and large TV with online services and WiFi, this is a great place to stay w family. They even have a parking spot a block away now. Lauren is an amazing host and responded immediately to any request as she’s right down the street. The only downside is on a weekend night it can get a bit loud being one block from several bars, but that’s the nature of being downtown . Highly recommended!
Guest favorite
A spacious living area features a sectional sofa facing an entertainment center with a flat-screen television. A ceiling fan hangs above, while light-toned wood flooring is complemented by a patterned area rug. An adjacent kitchen is partially visible, showcasing white cabinetry and modern appliances.
Home in Dubuque
4.9 out of 5 average rating, 129 reviews

Adorable 3-bedroom Modern Home

CarmenRating, 5 stars1 day ago
From start to finish, this was a great experience. The description and pictures matched and our party of 7 definitely fit comfortably. We cooked a few meals and had every pot, pan, and utensil I needed as well as a full grocery store about 5 minutes away! The price was also very reasonable.
Superhost
The exterior of a two-story house features gray siding and a welcoming red front door. A covered front porch with a small table and chairs offers outdoor seating. A stone accent wall complements the structure, while a balcony is visible on the upper level.
Home in Dubuque
4.85 out of 5 average rating, 120 reviews

3bed 2bath nestled in cozy Grandview neighborhood

BernaRating, 5 stars2 months ago
Thank you for your hospitality, great place at a good price. not to far from other good establishments.

Condo rentals in Galena

An aerial view captures the expansive resort area featuring a large pool surrounded by lounge chairs and umbrellas. The facility is set against a backdrop of green hills, with additional amenities visible, including a winding road leading to the complex.
Condo in Jo Daviess County
4.83 out of 5 average rating, 6 reviews

Lake Links Loft in Galena, Illinois

DavidRating, 5 stars3 months ago
Our family had a fantastic job at Dan's place. The location is great - close enough to the Eagle Ridge Inn and Owners Club, but very private location with a beautiful view of the lake. The unit had everything we need and was much larger than the pictures made it seem. Galena had great shopping and restaurants. Galena Territory Owners Club indoor pool was perfect for the kids. I'd recommend staying here anytime we make it back to Galena Territory!
Superhost
An indoor pool area features large windows allowing natural light to fill the space. The pool is surrounded by safety rails, with several swimmers enjoying the water. The ceiling is supported by wooden beams, adding to the open feel of the facility.
Condo in Jo Daviess County
4.8 out of 5 average rating, 5 reviews

Long Bay Point Unit C5

AlyxRating, 5 stars5 months ago
My husband and I stayed here for 4 nights. It's a 10 min drive from downtown Galena in a quiet wooded area with paved trails that you can take to the nearby amenities. The place was clean, quiet, and the bathtub was amazing! The gym and indoor/outdoor pool are very nice but about 1.5 miles from the condo which wasn't stated anywhere (or at least not anywhere we saw) and was a little disappointing but overall wasn't a huge deal. The restaurant is a short walk through the trails or you can drive to it. It's right next door. Also, the initial message you get after booking with the rules and asking to email them out of the app was a little daunting and not normal for Airbnb bookings. It just had a less "homey" experience that you expect from Airbnb. It made me slightly nervous but after everything I would certainly stay here again.
Guest favorite
An aerial view showcases a welcoming living room with a sectional sofa positioned near a stone fireplace. A patterned area rug contrasts with the wood flooring. Large windows allow natural light to fill the space, complemented by decorative elements like throw pillows and a coffee table.
Condo in Galena
5 out of 5 average rating, 16 reviews

Access to Pools and Lake Galena Marina #Dog Friend

JanelRating, 5 stars1 month ago
Absolutely amazing stay in Galena! We felt right at home. It was a perfect distance away from downtown, which was easily driveable, and absolutely quiet surroundings. We had everything we needed and was a great set up! Great communication with host and detailed responses about restaurant recommendations, directions to the home and check out instructions. Absolutely a must stay when traveling to Galena!
Guest favorite
The exterior of the historic building features a classic red brick façade, highlighted by large windows with prominent archways. A wide entrance is framed by dark-colored doors, leading to the vibrant business interiors. Overhead, architectural details showcase the building's rich history.
Condo in Dubuque
4.93 out of 5 average rating, 174 reviews

Montana House #302 - The Luxurious Downtown Stay

LeeRating, 5 stars2 months ago
Amazing location and incredible amount of work went into restoration. Clean and easily accessible
Superhost
A wide view of rolling hills is presented under a partly cloudy sky. Lush green fields and patches of trees create a serene landscape, while a small pond reflects the surrounding scenery. The tranquility of the countryside is evident in the natural setting.
Condo in Galena
4.67 out of 5 average rating, 3 reviews

Galena, IL, 2 Bedroom Q #2

KevinRating, 5 stars32 months ago
Very nice place. I would definitely stay there again!
Guest favorite
The historic building features a charming red brick exterior, flanked by mature greenery. A small patio with white metal chairs is visible, along with a decorative stone border. Large windows allow natural light to enter, contributing to a welcoming facade.
Condo in Galena
4.9 out of 5 average rating, 78 reviews

Driftless Get Away

PamelaRating, 5 stars1 month ago
i liked that it was accessible to main street. walking distance. it was however very noisy. Semis running by all Friday night. I loved the decor of the rooms. it had that old feel to it. reminded me of Grandma's place with the creeky floors. very roomy.
A spacious common area features high ceilings and large windows that fill the room with natural light. Comfortable seating is arranged around a stone fireplace, with an inviting dining table and bookshelves in the background, creating a warm and relaxing atmosphere.
Condo in Galena
4.86 out of 5 average rating, 7 reviews

Tranquil Retreat: Cozy 1BR Suite @ Wyndham Galena

James BrianRating, 5 stars2 months ago
The place is about 5 miles from Galena but not a bad drive to town. If possible, stay in a suite that has a view. Beautiful to wake up to & star gaze at night. The pool is big, the hot tub is hot, the fitness center is well-equipped, & the kid's rec room also. The lobby is huge with a nice fireplace. The suites are large & like a nice, small apartment. It was fun going thru the many shops downtown. Make sure you take some time to tour Galena's many beautiful old homes & buildings. Visit the visitors center by the river in the old depot & have breakfast or lunch across the street at Ottos'. Love this town!
Top guest favorite
An open living area features large sliding glass doors overlooking the Mississippi River and a balcony. A cozy seating arrangement includes a sofa and a chair. Natural light brightens the space, highlighting the laminate flooring and decor.
Condo in Bellevue
5 out of 5 average rating, 33 reviews

Gorgeous Riverview condo on the Mississippi

RandalRating, 5 stars6 months ago
Had a wonderful stay at Barbra’s place. Very inviting an well decorated, beautiful view over the Mississippi River where we viewed gorgeous sun rises and hunter moon reflection over the water. Highly recommend staying at Barbra’s place if your travel’s bring you to this area.

Quick stats about vacation rentals in Galena

  • Total rentals

    180 properties

  • Total number of reviews

    17K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    170 properties include access to wifi

Your guide to Galena

Welcome to Galena

With a history as rich as the mineral deposits for which it’s named, Galena is a charming small-town getaway in the heart of the Midwest and the county seat of Jo Daviess County. Though it seems unimaginable now, Galena once rivaled Chicago in population. Back in the late 1820s, thousands flocked here to mine its namesake ore, which had long been used by Native Americans for burial rituals and trading. Even an American president has called Galena home: Ulysses S. Grant’s mansion, presented to him by the townspeople in the 1860s, is one of the town’s most popular tourist destinations. Many Chicagoans call Galena their second home. Galena’s main street, sometimes called the Helluva Half Mile (riffing on Chicago’s Magnificent Mile), is lined with Victorian-era storefronts and eateries. The rolling hills along the horizon draw visitors for skiing in the winter and hot-air ballooning during the warmer months.


The best time to stay in a vacation rental in Galena

Galena rolls with the Midwestern weather patterns, which is good news for visitors. Perhaps the most beautiful times of year to visit are late spring, when the surrounding hills are in bloom, or autumn, during leaf-peeping season. Summertime in Galena is marked with outdoor bistro seating on Main Street, live music and festivals on the weekends, and strolling families wielding ice cream cones. Though winter is a little quieter (and can be quite cold), it has its own draws. Area resorts tucked into the hills host downhill skiers and snowboarders, and cross-country ski trails criss-cross through nearby nature preserves and Apple River Canyon State Park.


Top things to do in Galena

Great Galena Balloon Race

One of Galena’s best-known tourist attractions is also one of its most magnificent. Every third full weekend in June, weather pending, thousands come to marvel at a series of colorful balloon races across the prairie. The pros race at dusk on Friday night and at dawn on Saturday and Sunday. Meanwhile, amateurs can enjoy leisurely hot-air balloon rides with on-site rental companies.

Galena Grant Park

Toward the south end of bustling Main Street, a pedestrian bridge stretches across Galena River to this stately Victorian-era park. True to the period design, the park’s paths lead under decorative arbors to the town’s Civil War monument and gazebo, and the formal fountain stands out as a landmark.

West Street Sculpture Park

On the funkier side of Galena’s tourist attractions is this 2-acre park featuring metal sculptures of various scales. Ranging from rusted-out can contraptions to impressive postmodern art statements, the dozens of sculptures here are spread all over the park (including some in its trees), exposed to the elements, and open to visitors year round.

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Galena?

    Yes! Work meets play with ease at over 70 vacation rentals in Galena featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Galena?

    Four-legged friends are welcome in Galena. Choose from more than 40 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in bed and breakfast rentals in Galena?

    Experience the best of Galena with our bed and breakfast rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Galena have self check-in?

    Absolutely! We offer over 10 house rentals with self check-in in Galena. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

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  3. Illinois
  4. Jo Daviess County
  5. Galena