Family-friendly vacation 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, 125 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

4.98 out of 5 average rating, 120 reviews

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.

Cabin in Galena

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.

A tri-level house with a muted gray exterior features multiple large windows. A front porch with railings is visible, inviting relaxation. Surrounding greenery and a neatly maintained yard contribute to the peaceful setting. The sloped roof adds character to the home.

4.9 out of 5 average rating, 112 reviews

Cozy Wooded Tri-Level In Galena Territory

Relax with friends or the whole family at this wooded and peaceful place to stay in the Galena Territory.Cozy Tri-Level with 3 comfortable bedrooms and 3 baths. Tvs in 2 bedrooms as well as large tvs in the living room and downstairs rec room.Fireplace in living room area.Sit outside and enjoy the scenery on the front porch or back screened patio.Only 6 miles to Downtown Galena .Guests are welcome at Lake Galena,the Owners Club,Restaurants,Pools and Trails.Six Free passes are included.

4.98 out of 5 average rating, 120 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.

4.99 out of 5 average rating, 231 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

4.97 out of 5 average rating, 188 reviews

A screened porch offers comfortable seating with a sectional couch and a hanging chair, surrounded by windows that showcase wooded views. A coffee table sits at the center, accompanied by decorative plants and a large Connect 4 game on the side.

Cabin in Galena

Family Fun! Hot Tub•Fire Pit•Game Room•3 Kings!

Ultimate Family Escape in Galena Territory! Unwind, explore, and make memories at this chic, spacious cabin! Sip coffee on the deck as deer wander by, soak in the hot tub, and gather around the fire pit for s’mores. Relax on the screen porch or challenge the family with arcade games, air hockey, pinball, and darts! Enjoy Owner’s Club access with a pool, fitness center & pickleball. Adventure awaits—book your perfect getaway today! Family fun!-Hot tub-Fire pit-3 king beds-Game room

4.93 out of 5 average rating, 382 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

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, 601 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 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.

5 out of 5 average rating, 163 reviews

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.

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.

4.96 out of 5 average rating, 106 reviews

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.

4.98 out of 5 average rating, 132 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. 🌿

4.9 out of 5 average rating, 116 reviews

Cabin in Galena

Hot Tub l Fire pit I Chestnut Mt I 6 bed I 10 ppl

Escape to your own spacious mountain retreat just 8 miles from historic downtown Galena! 2 min to Chestnut Mountain. Enjoy a brand-new hot tub, fire pit with free wood, gas BBQ, and patio—perfect for summer nights or crisp fall days. Spend your days hiking, golfing, shopping, or taking scenic wine tours. In fall, explore vibrant foliage, festivals, and local charm. After your adventures, relax in comfort and style with plenty of space for the whole family.

Popular amenities for Galena family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a pool

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, 312 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

4.94 out of 5 average rating, 272 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

A spacious living area features a navy blue sectional sofa and a modern brown armchair. Large windows provide views of the surrounding greenery. A round, marble coffee table is centered in the room, with a fireplace beneath a mounted television, creating a cozy environment.

4.95 out of 5 average rating, 132 reviews

Cozy Galena Townhome

4.95 out of 5 average rating, 130 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

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

4.9 out of 5 average rating, 102 reviews

Firepit | Game room | Pool Access | Nature Views

An outdoor deck is shown featuring comfortable furniture and a fire pit table. The expansive, grassy area extends toward a picturesque golf course, framed by trees and distant buildings under a blue sky with scattered clouds.

4.95 out of 5 average rating, 111 reviews

King Suite • Jetted Tub • Fire pit • Golf Views

4.87 out of 5 average rating, 391 reviews

A spacious bedroom features a large bed with white bedding, complemented by wooden furniture. A comfortable couch sits nearby, illuminated by soft lamp light. Natural light filters through blinds on a glass door leading to an outdoor space.

Guest suite in Galena

Woodland Retreat

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 114 reviews

*Hot Tub*Screened Porch*Firepit*Owners Club

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, 153 reviews

Hot Tub Retreat • Firepit • 3BR/3BA • Dogs OK

4.92 out of 5 average rating, 100 reviews

Private Retreat, Hot Tub, Games, Pool Access

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.

4.95 out of 5 average rating, 195 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, 205 reviews

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

Apartment in Downtown Dubuque

A cozy living area features a gas fireplace surrounded by brown bricks. A charcoal tufted ottoman sits at the center, accompanied by a round mirror above a sleek side table. Light filters through wooden blinds, enhancing the warm tones of the hardwood flooring.

4.96 out of 5 average rating, 301 reviews

Drake House: The Loft with Private Hot Tub

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!

4.93 out of 5 average rating, 177 reviews

DunPuttin Place

Family-friendly home rentals with air conditioning

The charming craftsman-style house features a welcoming front porch with brick accents and a porch swing. A well-manicured garden with vibrant foliage adds a touch of color, while tall trees provide a natural backdrop. The entrance is framed by large windows, enhancing natural light.

4.95 out of 5 average rating, 197 reviews

Galena home close to Main St with parking and deck

A stone lion statue is positioned prominently at the entrance of a brick building. The lion faces forward, with its detailed mane and features clearly visible. Green-framed windows can be seen flanking the entrance, which is marked by a decorative door above a number.

4.98 out of 5 average rating, 161 reviews

Galena RowHouse - Downtown with parking included!

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.

5 out of 5 average rating, 211 reviews

The Downtown House - 1820s home steps from Main St

4.99 out of 5 average rating, 69 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

A modern kitchen features a large island with a marble countertop, complemented by dark wooden stools. Cabinets with a sleek gray finish line the walls, and patterned tiles add visual interest. Large windows allow natural light to brighten the space.

4.95 out of 5 average rating, 185 reviews

Historic Downtown 1852 Home - Newly Renovated

4.96 out of 5 average rating, 205 reviews

A spacious dining area features a long wooden table surrounded by upholstered chairs. A floral centerpiece adorns the table, while a decorative chandelier hangs above. The walls are accented with patterned wallpaper, and warm lighting complements the exposed ceiling beams. A cozy rug enhances the atmosphere.

Loft in Galena

Elle & Becks loft Suite

An open living area features a light-colored sectional sofa paired with a rustic coffee table. A dining table with black chairs is visible, along with modern kitchen appliances and cabinetry. Natural light flows through large windows, enhancing the inviting atmosphere of the space.

4.95 out of 5 average rating, 380 reviews

Downtown Gem for Two

The exterior of a colorful two-story home is presented, featuring patriotic flags adorning the front porch. Decorative pillars and a lattice design enhance the entrance. Two stone lion sculptures are positioned at the base of the steps, adding a distinctive touch to the welcoming facade.