Family-friendly vacation rentals in Galena

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, 138 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.

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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, 126 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.

HospitalityCleanlinessHot tubLocationFamilyComfortAmenitiesIndoor spacesOutdoor spacesAccuracyBathroomQuietSleep qualityNearbyKitchenViewBackyardConditionCheckoutPoolCheck-inLayoutGetting aroundGrillHikingDecorHeatingWifiAccessSkiingTVLaundryBeachNoiseValueEV charging

4.98 out of 5 average rating, 133 reviews

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.

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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, 118 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.

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A bright bedroom features a spacious bed covered with a dark throw blanket. A large window seat, adorned with cushions, offers views of the street. A small table and chair sit nearby, with hardwood flooring and elegant decor enhancing the room's character.

4.98 out of 5 average rating, 354 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.

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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, 221 reviews

Retro themed floating river cabin with a HOT TUB!

Our unique floating cabin features retro vibes and beautiful views of the Mississippi River backwaters. This cabin sits DIRECTLY in the water and has amazing views of the water You can even fish right off your deck! Enjoy the nature around you while sitting on your private floating deck, or snuggle up inside in front of the electric fireplace and Smart TV. This cabin features 2 bedrooms with queen beds, and a pull out couch in the living room. Our rental is located at Millennium Marina.

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4.99 out of 5 average rating, 236 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

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A cozy living area features a stone fireplace as the focal point, surrounded by large windows that provide views of the woods. A comfortable armchair and modern lamp are positioned nearby, while a TV and a stack of firewood add to the inviting ambiance.

4.97 out of 5 average rating, 196 reviews

Family Fall! Hot Tub•Fire In/Out•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

FamilyHospitalityIndoor spacesLocationComfortAmenitiesHot tubKitchenCleanlinessOutdoor spacesSleep qualityDecorAccuracyNearbyBathroomQuietViewAccessPoolLayoutTVPetsGetting aroundWalkabilityConditionCheck-inParkingHikingCheckoutSkiingGrillHeatingNoiseValue

4.93 out of 5 average rating, 390 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

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4.98 out of 5 average rating, 175 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. NO PETS ALLOWED.

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A spacious home is situated on a gently sloping landscape, framed by mature trees. The exterior features a combination of stone and wood elements, with a welcoming front porch and large windows that enhance natural light. A paved driveway leads up to the property.

5.0 out of 5 average rating, 102 reviews

Stunning 5 bdm home on The General in Galena Terr!

No MGMT Fees! Enjoy all that Galena Territory and Jo Daviess County has to offer! Nearly 5k sq ft with 5 bdrm/5.5 baths and located on the number one handicap hole on The General golf course with views of holes 12, 13, 14, 15 and 16! A one-of-a-kind location on over 2 acres of land. About 20 min from Downtown and Chestnut Mtn! Minutes from golf, hiking, horseback riding, boat rentals, fishing, indoor/outdoor pool, fitness center and game room at the Owner's Club!

HospitalityFamilyIndoor spacesCleanlinessLocationKitchenComfortAmenitiesViewHot tubSleep qualitySkiingOutdoor spacesAccuracyGetting aroundPoolConditionBathroomNearbyQuietAccessCheckoutCheck-inTVGrillHikingLayoutLaundryValueDecorHeatingParkingWalkabilityShared spacesEV chargingAir conditioning

An expansive recreational area features warm wooden flooring and exposed brick walls. Comfortable seating arrangements include a sectional sofa and armchairs. A pool table is positioned center stage, with a wall-mounted television nearby. Large windows allow natural light to fill the space, creating an inviting ambiance.

4.95 out of 5 average rating, 462 reviews

Gameroom in Galena

In the center of downtown Galena, we offer over 1500 sq ft. in a 1852 building. A bay window offers 180° view of Main St. A pool table, shuffleboard, pinball machine and bar are at your disposal. You'll have access to either Main Street from the front or Bench Street from the back. There is free parking on South Main Street and out the back on South Bench Street. There is no dedicated parking spot but parking opens up quit a bit in the evenings.

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Popular amenities for Galena family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a pool

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, 132 reviews

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

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A warm living area features a brick fireplace with a mounted television above it. Large skylights and windows allow natural light to fill the space. A coffee table stands at the center, adorned with decorative items, complemented by comfortable seating and a vibrant area rug.

4.97 out of 5 average rating, 131 reviews

Secluded Treehouse w/great views from every room!

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Superhost

A spacious living room features a stone fireplace as a focal point, surrounded by large windows offering natural light. A comfortable sofa is complemented by two leather chairs. A dark coffee table sits in the center with decorative items, creating a cozy gathering space.

4.82 out of 5 average rating, 119 reviews

Log Home/Firepit/Game Room/Hot tub

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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, 145 reviews

Cozy Galena Townhome

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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

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4.96 out of 5 average rating, 117 reviews

King Suite • Jetted Tub • Fire pit • Golf Views

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4.94 out of 5 average rating, 279 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

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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, 106 reviews

Inviting & Bright | Firepit Sauna Hot Tub & Games!

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Family-friendly home rentals with a hot tub

Superhost

4.87 out of 5 average rating, 125 reviews

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

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4.97 out of 5 average rating, 144 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

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4.87 out of 5 average rating, 394 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

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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, 121 reviews

Lake Views | Hot Tub | Nature Retreat | Movie Room

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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, 320 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

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4.93 out of 5 average rating, 178 reviews

DunPuttin Place

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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, 213 reviews

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

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Apartment in Downtown Dubuque

A cozy living room features exposed brick walls, a comfortable sectional sofa, and a round coffee table. A flat-screen TV is mounted above a wooden console, while natural light enters through the window with wooden blinds. Decorative wall art enhances the space.

4.91 out of 5 average rating, 430 reviews

Drake House: Fleur de Lis with Private Hot Tub

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Family-friendly home rentals with air conditioning

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, 191 reviews

Historic Downtown 1852 Home - Newly Renovated

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4.82 out of 5 average rating, 754 reviews

A stylish open room features exposed brick walls and hardwood floors. A spacious bed with a patterned blanket is positioned against the back wall. Colorful artwork adorns a nearby wall, while a rustic table and purple chairs provide seating options in the living area.

Loft in Galena

The Loft Apartment Main Street Galena

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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, 203 reviews

Galena home close to Main St with parking and deck

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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.

4.9 out of 5 average rating, 203 reviews

Nine Star Suites - 1 Block to Main Street!

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A brightly lit sitting area is adorned with large windows dressed in golden curtains. A plush couch is positioned adjacent to a day bed covered with a white blanket. A decorative rug lies beneath, complementing the wooden flooring and surrounding art on the walls.

4.88 out of 5 average rating, 103 reviews

Quiet 2 Bedroom Main Street Apt.

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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, 167 reviews

Galena RowHouse - Downtown with parking included!

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4.98 out of 5 average rating, 147 reviews

The interior space features a spacious living room with a large sectional couch and a wooden coffee table. Exposed wooden beams stretch across the ceiling, enhancing the cabin's rustic charm. The open layout connects to a modern kitchen, visible in the background.

Cabin in Hazel Green

Crooked Creek Cabin

CleanlinessLocationComfortDecorHospitalityAmenitiesIndoor spacesAccuracyNearbyGetting aroundQuietOutdoor spacesSleep qualityFamilyKitchenBathroomTVGrillConditionWifiViewCheck-inValueParksLayoutLaundryWalkabilityBackyardNoise