Family-friendly vacation rentals in Galena

A two-story house with a light-colored facade is visible. The entrance features a covered porch with decorative columns and flower pots. Windows are framed in black, and a ramp provides accessibility, leading to the front door. The surrounding area includes a nearby brick structure.

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!

4.88 out of 5 average rating, 126 reviews

The exterior of the cabin features a welcoming wooden facade complemented by a front porch with a railing. A well-kept garden with various flowers rests by stone steps leading up to the entrance, surrounded by lush greenery and natural elements.

Cabin in Galena

Serenity Cabins - A rustic, yet upscale cabin!

SunnyRating, 5 stars6 months ago

I felt super confident in my booking right from the moment I booked it as Dan guided me the entire way and is super amazing at responding and communicating. It was super accomodating when I needed help and it was so reassuring to have a host so kind and responsible.

A spacious bathroom features dual sinks set in a wooden vanity, surrounded by mirrors. Soft rugs add comfort underfoot, while a storage bench and hanging towels provide convenience. Natural light enters through a nearby window, highlighting the earthy color palette and inviting atmosphere.

4.92 out of 5 average rating, 117 reviews

Boulder Creek

KaterynaRating, 5 stars3 months ago

This place is so cozy! Really great for Christmas & New Year time. We even did not need to bring Christmas tree - it was there, fully decorated, which gave us feeling like we were at home. Very peaceful location, but close to Galena downtown and ski resort.

4.86 out of 5 average rating, 155 reviews

A spacious living area is furnished with a large sectional sofa in a deep blue hue, complemented by two dark wood coffee tables. Natural light filters through two windows adorned with simple trim, highlighting the textured area rug beneath. Exposed brick adds a touch of character to the room.

Townhouse in Dubuque

117 Saint Marys | Downtown Dubuque

ColetteRating, 5 stars1 month ago

We enjoyed our stay in Dubuque. The location had everything we were looking for -- walkability, space to stretch our legs, quiet atmosphere. Nick was extremely helpful when we accidentally locked a closet door -- his crew offered a swift response and a speedy solution. A very well-kept historic home in a neat little neighborhood. We hope to be back!

4.99 out of 5 average rating, 234 reviews

The farmhouse is shown from the exterior, showcasing a two-story structure with white siding and a covered front porch. Flower planters hang from the porch railing, and a stone pathway leads to the entrance. Green grass surrounds the house, bordered by a paved area.

Home in Gratiot

The Old Farmhouse

JenniferRating, 5 stars1 month ago

Well-kept, serene, and charming. This place is ideal for a relaxing getaway. The Farmhouse, set in the rolling hills of the Wisconsin countryside, is spacious and inviting and guests can expect a quiet, comfortable stay with all the amenities of home. We thoroughly enjoyed our long weekend at the Farmhouse.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Galena family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a pool

4.92 out of 5 average rating, 79 reviews

A blue double door opens to reveal a welcoming entryway with wood-paneled ceilings and a patterned area rug. A staircase is visible in the background, leading to an upper level. Natural light floods in through a side window adorned with potted plants.

Home in Apple River

The Ho Hum East on Apple Canyon Lake

LatashaRating, 5 stars7 months ago

Alex was a Great host! His lake house was clean and cozy.. The view was beautiful! My children and I really enjoyed ourselves.. Thanks Alex!!

A scenic view of rolling hills at dusk is presented, with a colorful sunset displaying shades of pink and purple in the sky. The horizon is lined with trees and distant hills, contributing to a serene rural landscape.

4.55 out of 5 average rating, 38 reviews

Galena Territory overlooking sublime valley

YeseniaRating, 5 stars9 months ago

Loved our stay here! Such a lovely weekend home away from home with breathtaking views!

A spacious gathering room features a large sectional sofa with multiple cushions, complemented by a coffee table at its center. Natural light enters through several windows, illuminating the warm wood details of the ceiling and the earthy tones of the wall.

5 out of 5 average rating, 3 reviews

Redtail Retreat, Galena Territory

MattRating, 5 stars51 months ago

Had a lovey stay. Beautiful clean home. Was nice to come back to after snowboarding at Chestnut. We will visit again.

A stone entrance sign for the Galena Territory and Eagle Ridge Inn & Resort is prominently displayed, surrounded by lush greenery and vibrant flower beds. The clear blue sky above adds to the welcoming aspect of the resort's entrance.

4.96 out of 5 average rating, 108 reviews

Galena Territory Home with full resort amenities**

MarianneRating, 5 stars8 months ago

This is the 2nd time I booked Laurie's place, so you know we were pleased the first time. It didn't disappoint. Last time was for our son's wedding, this time was for our future daughter-in-law's girls' weekend. House was perfect for hanging out, close to downtown for shopping and a night out.

4.67 out of 5 average rating, 15 reviews

Villa in Galena

HELLO Spring! 2 BR Golf Villa w/access to pools, f

BradleyRating, 5 stars7 months ago

Great place, very beutiful area, peaceful and quiet, short drive to Galena, and the Iowa state line

4.84 out of 5 average rating, 76 reviews

A gravel pathway leads up to a rustic log cabin, softly illuminated by warm lighting from the windows. Surrounding vegetation includes manicured grass and a stone border, creating a natural frame against the evening sky.

Cabin in Elizabeth

Homestead Hideaway Seven Sisters Suite

JamesRating, 5 stars1 month ago

Enjoyed our trip to Galena and our stay in Elizabeth at the bnb. Only wish the temperature was warmer the weekend we was there but still had a good time

The exterior of the home is surrounded by lush greenery, showcasing a blend of trees and shrubbery. The light-colored siding of the house complements the natural setting. A spacious yard is visible, providing a tranquil atmosphere amid the woods.

4.9 out of 5 average rating, 10 reviews

14 Southridge Drive The Galena Territory

HeatherRating, 5 stars6 months ago

excellent location, fast and easy to downtown shops, or to explore the amenities. amazing restaurants, felt safe. will stay again.

A two-story home is set among lush greenery, featuring a sloped roof with multiple gables. The front porch is accessed by a short wooden step, and a walkway leads to a centrally located front door. Windows on each side allow natural light to enter.

4.88 out of 5 average rating, 64 reviews

Cozy 2 bedroom home with fireplace

KarenRating, 5 stars6 months ago

This is the 2nd time we've gotten a Rosebud property and, as always, never disappointed!! Will be back again, soon!!!

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Family-friendly home rentals with a hot tub

Aerial view of a two-story home surrounded by expansive green lawns and trees. The house is framed by a circular driveway and features a wraparound porch. The surrounding landscape showcases rolling hills and dense foliage, creating a serene, natural atmosphere.

4.78 out of 5 average rating, 18 reviews

HUGE 6 BR Near Shenandoah Riding Ctr - Private Hot

JingwenRating, 5 stars9 months ago

Recommended place to stay with families

A log cabin exterior is surrounded by lush green trees. The structure features a sloping roof, large windows that allow natural light, and a welcoming porch. A grassy area lies in front, creating a serene setting that blends with the natural surroundings.

Cabin in Galena

4.66 out of 5 average rating, 120 reviews

True Log Cabin (8ppl) - Jacuzzi, Nature, Lake

BransonRating, 5 stars2 months ago

This cabin was fully stocked with amenities, linens, soap, washing detergent, kitchen equipment and was super clean. The area around the cabin peaceful and relaxing, perfect for a cabin getaway. Definitely worth the price.

A two-story home is showcased with earthy green siding and a brown shingled roof. Large front windows allow natural light to fill the space. A covered porch is visible, surrounded by a well-maintained lawn and mature shrubs, creating a welcoming appearance.

4.72 out of 5 average rating, 57 reviews

Fabulous Home Away From Home

GinaRating, 5 stars5 months ago

My family of 5 traveled to Galena over Thanksgiving and stayed in this home. It was very comfortable and clean, and my family had a wonderful visit. Everything in the home was as described, and Stephen was quick to respond to any questions that I had. The town is charming, and quaint. We went on a ghost tour, shopped downtown and went to Grant’s home. We would 100% stay at Stephen’s place again if we ever go back to Galena!

4.9 out of 5 average rating, 368 reviews

A modern living room features a sectional sofa adorned with colorful cushions, paired with a wooden coffee table. Visible are warm wood floors and a chic rug. An open layout reveals a dining area and a glimpse of the adjoining kitchen. A doorway leads to a bathroom.

Apartment in Dubuque

Drake House: City View with Private Hot Tub

BetsyRating, 5 stars2 weeks ago

This was my second time staying at Jenn’s place and it was great, again! Very clean and comfortable! Will be back and would recommend to anyone!

5 out of 5 average rating, 9 reviews

The exterior of the Gehlen House Inn is presented, showcasing a two-story building constructed from beige limestone. Colorful flower boxes adorn the windows, enhancing the inviting appearance. A set of stairs leads to the entrance, with trees lining the property, contributing to the quaint atmosphere.

Home in Saint Donatus

Luxemburg Beauty- The Gehlen House Inn

JillRating, 5 stars4 months ago

What a great place and great hosts! Nice of Don to share history of the place. One of the best stocked places we've stayed. Also very clean with plenty of bedding and towels! The barn located behind is wonderful--great pizza, great beers and plenty of room. Truly one of the best places we've stayed.

4.67 out of 5 average rating, 3 reviews

A wooded exterior view captures the resort's charming architecture, showcasing a stone accent at the entrance. Surrounding greenery and manicured landscaping enhance the inviting appearance of the building, set against a clear blue sky.

Condo in Galena

Galena, IL, 2 Bedroom Q #2

KevinRating, 5 stars32 months ago

Very nice place. I would definitely stay there again!

4.9 out of 5 average rating, 10 reviews

Spring has Sprung @ Fore Augusta ~ Huge Fire Pit,

TiffanyRating, 5 stars10 months ago

Great price for a lovely weekend. Group of ten were comfortable and had plenty of privacy. We went for the balloon festival which we could see from the yard. Plenty of towels for hot tub. Thank you!

A welcoming living area features leather armchairs arranged around a round coffee table. A large flat-screen TV is mounted on the wall, alongside built-in shelves displaying various decor. Natural light fills the space through expansive windows, showcasing the warm wood accents in the ceiling.

4.72 out of 5 average rating, 25 reviews

Amazing 6 BR Home! Whiskey Room! Pool Table! Karao

DanaRating, 5 stars2 months ago

Perfect house for two families of 4. Everything was clean and exactly how it was described. Kids loved the pool table, hot tub, karaoke machine, and upstairs lounge area. The kitchen was well equipped, and the coffee bar was so nice in the mornings. Comfiest beds ever. I loved spending time in the 'whiskey room'. So cozy! All weekend we kept saying how wonderful the house was for our group. Definitely would stay there again!

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Family-friendly home rentals with Wifi

4.9 out of 5 average rating, 115 reviews

A light-filled living space features a dining area with a round table and four chairs. A comfortable sofa and an armchair are positioned around a coffee table. Tall windows allow natural light to brighten the room, while a large wall clock adds a practical touch.

Apartment in Dubuque

1890's Historic District Guesthouse - Apartment #2

CheyanneRating, 5 stars6 months ago

Great location that is walking distance from a lot of places. Cathy responds fast and shows she really cares about your experience.

4.89 out of 5 average rating, 62 reviews

An entrance to the property is shown, featuring a wooden door framed by large glass panels. Green bushes and flower pots with blooming plants are situated on either side of the stone path, which leads to the door. A striped awning provides shelter above.

Apartment in Elizabeth

Derinda house B&B private apartment.

TiffanyRating, 5 stars4 days ago

This was my fourth time staying at Sandys and each time is just as enjoyable as the last. Her new wallpaper in the kitchen, bedrooms, and master bath are beautiful. She has a real knack for decor. She's always super helpful, kind, and her breakfasts dont disappoint! If you're looking to relax in a peaceful setting, but still be close to downtown Galena, this is THE place to stay.

An outdoor patio is framed by wooden trellises, providing shade and a welcoming gathering space. Various seating arrangements include round and rectangular tables, complemented by potted flowers. Scenic valley views are visible in the background, enhancing the tranquil ambiance.

Barn in Epworth

4.97 out of 5 average rating, 29 reviews

Lattnerville Church Inn

JessicaRating, 5 stars22 months ago

The pictures do not do this beautiful church/home jusitice. There is so much space and the views from outside are stunning. Thank you so much for allowing us to stay in such a beautiful and meaningful home.

The exterior of the Captain Merry Mansion features a combination of brick and stone, showcasing a central tower with a lighthouse-like structure. Surrounding greenery and a paved pathway lead up to the welcoming entrance, which is highlighted by large glass doors and the property's name elegantly displayed.

Villa in East Dubuque

4.75 out of 5 average rating, 84 reviews

Merry Mansion

AmyRating, 5 stars4 months ago

The Merry Mansion was perfect for our family; we had several people staying, but were able to host some additional local family members for meals - a huge kitchen provided plenty of space for meal preparation and the two dining rooms provided more than ample space for enjoying our home-cooked meals together. The decor is lovely and there was plenty of space for privacy in bedrooms or socializing in the two living rooms. It is conveniently located to both Dubuque and Galena and walkable to establishments in East Dubuque. Corey was wonderful, a proactive communicator and very responsive to questions; he was available at check-in to provide a very helpful tour of the mansion, as well. We will be back again for another Christmas celebration!

4.89 out of 5 average rating, 195 reviews

An inviting living area features two comfortable couches adorned with decorative cushions. A glass coffee table sits atop a patterned rug, showcasing books and magazines. Artwork adorns the walls, and track lighting highlights the ornate ceiling details.

Apartment in Dubuque

1890's Historic District Guesthouse

JennRating, 5 stars5 months ago

Cathy was super responsive and answered our questions right away. Her place is clean, simple, cozy, and just as described — it was a perfect home-away-from-home stay for us.

4.87 out of 5 average rating, 753 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

CatherineRating, 5 stars3 weeks ago

Such a great stay! The location couldn’t have been better—convenient and easy to find. The complimentary coffee downstairs was absolutely delicious and a nice bonus. The room had a cozy, charming vibe and was very clean. All in all, a great value and totally worth it. I’d stay again in a heartbeat!