Family-friendly holiday rentals in Galena

The exterior of the home is showcased, highlighting a multi-level structure surrounded by lush greenery. Large windows reflect warm indoor lighting, and a spacious deck is visible, featuring Adirondack chairs positioned near the lawn, offering ample space for relaxation and outdoor enjoyment.

4.96 out of 5 average rating, 126 reviews

Treehouse! 3BR Ensuites•Secluded• Hot Tub•Fire Pit

🌲7 minutes to Owner's Club 🌲10% Weekly Discount 🌲3 BRDM+3.5 BTH (all ensuite) 🌲Secluded + Spacious on 2-acre lot 🌲Hot tub! 🌲Smokeless firepit (wood provided)🪵 🌲Year-round community indoor pool & seasonal outdoor pool 🏊‍♂️ + zero entry kiddie pool 🌞 🌲Open concept main level 🌲Games & puzzles for all ages 🧩 🌲Axe throwing game 🎯 🌲Large connect 4 game & jenga 🌲New & fully equipped kitchen 🍽️ 🌲Kid & Dog friendly 👧🏼🐶 🌲Seasonal valley views 🌲Gym access 🌲High-speed internet

FamilyIndoor spacesPool

4.99 out of 5 average rating, 135 reviews

* 10 min Walk to Main Street*Stocked kitchen*

Take a step back in time in this 1840s era home! Newly renovated with an eye to maintaining it's vintage charm, this house fits right into Galena's historic character. Grab your morning coffee on the side porch swing. Take the 10 min walk to Main Street for shopping and lunch. Relax in the light filled living room or fully stocked kitchen. Or, enjoy front porch rockers. Be sure to keep an eye out for some historic surprises in the house. NOTE: There are a lot of stairs to the side porch entry.

KitchenIndoor spacesDecor

A well-maintained cabin is set amid lush greenery, featuring a stone accent facade. The exterior includes a two-car garage with a vibrant teal door, and a welcoming porch with blue chairs inviting relaxation. Spacious lawns surround the cabin, enhancing the natural setting.

4.98 out of 5 average rating, 122 reviews

Fast Wi-Fi | EV Charger | Fireplace | Hot Tub

Unwind in our comfortable Galena Territory cabin with 3 bedrooms, 3 full baths and sofa sleeper. EV Charging outlet in garage. Strong Eero boosted Wi-Fi; Roku streaming on every floor. Stone wood burning fireplace. Three-season room with scenic sunrise and wooded views. Lower-level walkout to patio with hot tub, fire pit and beautiful stargazing. Minutes away from the Lake Galena Marina, golf, tennis, pool, and fitness center. 15 mins from Chestnut Mountain and historic downtown Galena.

Indoor spacesFamilyBeach

A custom log cabin is framed by lush greenery and manicured landscaping. The warm wooden exterior features multiple gabled roofs and large windows. A stone pathway leads through the vibrant garden, creating an inviting approach to the entrance.

4.96 out of 5 average rating, 135 reviews

Private, Galena Log Cabin

This custom log cabin is the perfect getaway for friends & family seeking the solitude of the Galena Territory and fine dining and shops just 10 minutes away on Galena's Main Street. Each of the 3-levels offers an owner's suite with bath. Cozy up to 2 fireplaces, grill on the deck, or make 'smores at the firepit. The cabin has high speed, fiber internet and the lower-level walkout features a 55” flat screen TV. Guests can access swimming pools & pool tables at the Owner's Club 7 minutes away.

Indoor spacesFamilyDecor

4.98 out of 5 average rating, 125 reviews

An inviting firepit area features two black Adirondack chairs positioned around a circular stone firepit. The A-frame cabin is seen in the background, softly illuminated by decorative lights, surrounded by trees at dusk.

Cabin in Elizabeth

Hot Tub+ Firepit+ "Tiny"house+ Views+ Near Galena

Tucked away in the countryside of Galena, our charming A-frame cabin is the perfect escape for those seeking peace, nature, and a touch of nostalgia. This intimate retreat blends mid-century modern charm with cozy modern comforts, creating an unforgettable getaway. Whether you’re sipping coffee on the deck at sunrise, soaking in the brand-new hot tub under a canopy of stars, or unwinding by the fire with a vinyl record spinning in the background, every moment here is designed for relaxation.

Indoor spacesFamilyCheck-in

4.94 out of 5 average rating, 209 reviews

Family Fun! Xbox-Hot tub-Firepit-Games in/outdoor!

Enjoy the ultimate summer retreat at our stylish 4-bedroom cabin in Galena Territory! New furniture and Xbox just added! Sip your morning coffee on the deck, explore nearby trails or relax in the hot tub. Challenge family and friends to arcade games, air hockey, darts, and board games. With 8 amenity cards, access the Owner’s Club for swimming, fitness, and indoor pickleball—rackets and balls provided! Whether you seek adventure or relaxation, this cabin is your perfect summer getaway!

FamilyKitchenCondition

4.99 out of 5 average rating, 233 reviews

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

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

Indoor spacesKitchenCheckout

4.93 out of 5 average rating, 384 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

Indoor spacesFamilyAir conditioning

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.

4.96 out of 5 average rating, 603 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!

Indoor spacesFamilyGetting around

5 out of 5 average rating, 165 reviews

A modern living area features a cozy seating arrangement with two armchairs and a plush sofa. A decorative rug lies beneath a coffee table, while a television is mounted above a fireplace. Large windows provide natural light, complemented by artwork on the walls.

Apartment in Galena

Ulysses Suites, Suite 303

Ulysses Suites has just been completed inside the historic J. G. Schmohl building in the heart of downtown Galena, located at 213 to 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. The Presidential Suite 303 is located on the 3rd floor.

KitchenIndoor spacesCheck-in

4.96 out of 5 average rating, 107 reviews

A spacious living area features a contemporary black sofa set, complemented by a sleek area rug. Exposed brick walls and wooden beams create a cozy atmosphere. A well-equipped kitchen is visible in the background, enhancing the open layout. Natural light floods in from large windows.

Apartment in Galena

Suite Victory #3 On Main St w/Reserved Parking

Suite Victory #3- 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. NO DOGS ALLOWED.

Indoor spacesKitchenCheckout

4.98 out of 5 average rating, 134 reviews

The living area features a high wooden ceiling with a unique chandelier. Comfortable seating is arranged around a coffee table, accompanied by a rustic design. A kitchenette is visible in the background, along with large windows allowing natural light to enhance the open space.

Cabin in Hazel Green

Deer Trail Cabin

🌿 Cozy cabin tucked in the quiet Wisconsin woods—your perfect spring retreat. Enjoy fresh air, blooming trees, and peaceful forest trails right outside your door. Relax in the outdoor hot tub under the stars, gather around the fire pit in the evening (bring your own wood or collect from the property), and watch the free-range goats and chickens roaming the property. A peaceful, private getaway for couples, small families, or anyone looking to unwind in nature. 🌿

FamilyIndoor spacesValue

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.

4.96 out of 5 average rating, 314 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

Indoor spacesKitchenOutdoor spaces

4.97 out of 5 average rating, 137 reviews

Spacious-Hot Tub-Pool Table-6 Bedroom-6 Bathroom

Indoor spacesKitchenPets

Place to stay in East Dubuque

A hot tub is positioned on a private deck, surrounded by scenic views of the Mississippi River backwaters. The calm water reflects greenery from the banks, while a seating area with dark outdoor furniture is visible nearby.

4.96 out of 5 average rating, 216 reviews

Retro themed floating river cabin with a HOT TUB!

KitchenIndoor spacesAir conditioning

4.88 out of 5 average rating, 110 reviews

Hot Tub | Fireplace | Screened Porch | Pool Access

Indoor spacesFamilyHiking

A hot tub is positioned outdoors, with bubbling water visible, offering a view of lush greenery and rolling hills in the background. The scene is framed by a tree, creating a serene and inviting atmosphere for relaxation.

4.97 out of 5 average rating, 102 reviews

Where the Hot Tub Faces the Fairway

FamilyKitchenCondition

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, 207 reviews

*Covered Hot Tub * 2 Fire Tables * Massive Deck*

FamilyKitchenComfort

An outdoor deck features a spacious hot tub surrounded by a wooden railing. Nearby, two wooden benches and a table provide additional seating. Sunlight filters through the surrounding greenery, casting a natural warmth on the deck.

4.97 out of 5 average rating, 119 reviews

Lake Views | Hot Tub | Nature Retreat | Movie Room

FamilyIndoor spacesSkiing

A modern living room features a comfortable seating arrangement with a light gray sofa and armchair. A large window allows natural light to fill the space, while a flat-screen TV is mounted above a cozy fireplace. Built-in shelves are neatly arranged with books and decorative items.

4.98 out of 5 average rating, 105 reviews

Inviting & Bright | Firepit Sauna Hot Tub & Games!

FamilyIndoor spacesValue

Family- and pet-friendly home rentals

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, 219 reviews

Galena Getaway

Indoor spacesKitchenBarbecue

Superhost

The exterior of the home is shown, featuring a wooden deck leading to the entrance. An American flag is displayed at the front, with trees surrounding the property and views of Lake Lacoma visible in the background. A gravel area provides parking space.

Home in East Dubuque

4.86 out of 5 average rating, 226 reviews

2 Bedroom Lakefront Cabin W/ Deck, Boats & Dock

FamilyKitchenCondition

A cozy living area is highlighted by a wood-burning fireplace and a large window showcasing lush outdoor views. Comfortable seating includes a gray sofa and an armchair, while a coffee table sits at the center. A flat-screen TV is mounted above the fireplace, complementing the inviting space.

4.98 out of 5 average rating, 120 reviews

Spacious, King Beds, Pool steps away, Near Golf

KitchenIndoor spacesLayout

4.88 out of 5 average rating, 366 reviews

A wooden side table is adorned with a decorative tray holding candles and pebbles. Above, a framed artwork showcases a cityscape, while a wall clock displays the time. A framed certificate and a ceramic figure add character to the space.

Home in East Dubuque

Cozy Oasis/DBQ/FieldDreams/Galena-Fenced for Pets

KitchenFamilyGetting around

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.

4.89 out of 5 average rating, 134 reviews

Serenity Cabins - A rustic, yet upscale cabin!

KitchenIndoor spacesComfort

4.96 out of 5 average rating, 109 reviews

A spacious living area is highlighted by a cozy seating arrangement featuring colorful chairs and a comfortable sofa. Natural light fills the room through large windows, while a fireplace and a wall-mounted TV create a central focal point. Decorative items and warm wooden accents enhance the welcoming feel.

Townhouse in Galena

Townhome in Galena Territory w/ Pools, Lake, Gym

Indoor spacesKitchenHospitality

4.96 out of 5 average rating, 113 reviews

King Suite • Jetted Tub • Fire pit • Golf Views

Indoor spacesFamilyAmenities

4.88 out of 5 average rating, 156 reviews

An aerial view of the living room is displayed, showcasing a dark leather sectional couch positioned around a textured area rug. A wooden coffee table is centered in the space, while a flat-screen television is positioned next to a large stone feature wall. Natural light fills the room through large windows.

Villa in Galena

Spring Creek Sanctuary-2BR-Owners’ Club Access

KitchenIndoor spacesValue

Family-friendly home rentals with a pool

4.94 out of 5 average rating, 274 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

Indoor spacesKitchenAmenities

4.99 out of 5 average rating, 70 reviews

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.

Cottage in Galena

Storybook Countryside Cottage

KitchenFamilyAmenities

Superhost

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.

4.8 out of 5 average rating, 107 reviews

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

KitchenFamilyWalkability

4.95 out of 5 average rating, 133 reviews

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.

Townhouse in Galena

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

KitchenFamilyDecor

4.91 out of 5 average rating, 108 reviews

A bright living room features large arched windows that provide natural light and views of the outdoors. A gray sofa and a red accent chair are arranged around a modern coffee table. A wall-mounted Smart TV is positioned above a sleek fireplace, creating a cozy focal point.

Townhouse in Galena

Cozy villa near downtown Galena!

KitchenIndoor spacesQuiet

5 out of 5 average rating, 29 reviews

Hot Tub, Sunroom, Pool Table, Arcade | 4BR, 3.5BA

FamilyIndoor spacesBathroom

Home in Thompson Township

4.9 out of 5 average rating, 10 reviews

Lake Retreat - Hot Tub, Game Room & Two-Tier Deck

FamilyIndoor spacesAccuracy