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, 132 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

KitchenFamilySleep quality

4.98 out of 5 average rating, 141 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 spacesLayout

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, 139 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.

FamilyKitchenTV

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.

FamilyKitchenNearby

4.98 out of 5 average rating, 131 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.

KitchenFamilyDecor

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

FamilyIndoor spacesCondition

The exterior of the cabin is framed by trees, with warm lights glowing from within. A covered entrance leads to the front porch, which features wooden steps and stone accents. Fallen leaves cover the ground, enhancing the rustic appeal against a dramatic sunset sky.

4.97 out of 5 average rating, 194 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

KitchenIndoor spacesSkiing

4.93 out of 5 average rating, 389 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

KitchenIndoor spacesHeating

5.0 out of 5 average rating, 167 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.

FamilyIndoor spacesParking

4.96 out of 5 average rating, 113 reviews

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 PETS ALLOWED.

Indoor spacesKitchenSleep quality

Superhost

4.87 out of 5 average rating, 124 reviews

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.

Indoor spacesKitchenNearby

4.99 out of 5 average rating, 419 reviews

A decorative sign reading 'Dawson's Remise' is illuminated in warm tones, framed in black wood. Next to it is a textured pillow featuring a geometric red and black pattern, adding a modern touch to the setting.

Apartment in Galena

Dawson's Remise Luxury Accommodation

Enjoy a luxurious stay in our remise ("carriage house"), complete with authentic Art Deco and Industrial furniture and design. We took great care in ensuring top notch craftsmanship and amenities, so as to create an inviting environment that you won't want to leave! Hidden away off the quaint and historic Park Avenue, you'll enjoy a quiet and restful stay whilst within walking distance to Main Street Galena and all it has to offer.

KitchenIndoor spacesAccuracy

Popular amenities for Galena family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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!

KitchenFamilyWalkability

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.

4.81 out of 5 average rating, 118 reviews

Log Home/Firepit/Game Room/Hot tub

Indoor spacesKitchenQuiet

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, 202 reviews

Awesome Lodge in Galena Territory

FamilyKitchenView

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, 101 reviews

Stunning 5 bdm home on The General in Galena Terr!

KitchenFamilyHeating

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, 319 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

Indoor spacesFamilyValue

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

Indoor spacesFamilyAmenities

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, 211 reviews

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

KitchenFamilyPets

4.96 out of 5 average rating, 141 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

KitchenFamilyAmenities

Family- and pet-friendly home rentals

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, 604 reviews

Beautiful Miner's Cottage in a Garden

Indoor spacesKitchenParking

An electric fireplace is positioned below a large flat-screen TV mounted on a stone mantel, which adds texture to the living space. A comfortable armchair is shown with a patterned upholstery, and natural light filters through nearby windows, illuminating the inviting decor.

4.97 out of 5 average rating, 207 reviews

Newly Renovated. Gorgeous Retreat!

KitchenIndoor spacesDecor

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, 130 reviews

Secluded Treehouse w/great views from every room!

KitchenIndoor spacesView

4.88 out of 5 average rating, 157 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

FamilyIndoor spacesCondition

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, 220 reviews

Galena Getaway

KitchenIndoor spacesLocation

4.96 out of 5 average rating, 117 reviews

King Suite • Jetted Tub • Fire pit • Golf Views

FamilyKitchenHiking

4.98 out of 5 average rating, 125 reviews

Spacious, King Beds, Pool steps away, Near Golf

KitchenFamilyNearby

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!

KitchenFamilyQuiet

Family-friendly home rentals with a pool

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.

4.78 out of 5 average rating, 109 reviews

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

FamilyKitchenWalkability

4.94 out of 5 average rating, 279 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

FamilyIndoor spacesParking

4.96 out of 5 average rating, 163 reviews

A spacious dining area features a large wooden table surrounded by black chairs. A living space is visible in the background with comfortable seating, large windows, and a sleek gas fireplace. Natural light fills the room, highlighting the open and airy layout.

Holiday home in Galena

Summer in Galena | Hot Tub, Fire Pit & Views

FamilyKitchenSkiing

4.9 out of 5 average rating, 205 reviews

A welcoming living area features a vaulted ceiling and large windows that provide views of the outdoors. A brick fireplace adds warmth, while comfortable seating is arranged around a coffee table. Soft lighting enhances the cozy atmosphere, complemented by decorative plants and artwork.

Townhouse in Galena

The Airy Aerie: Owners' Club access, golf nearby!

FamilyIndoor spacesHeating

A round dining table is set outdoors with four yellow plates, each topped with a drink garnished with olives and celery. A bottle of cocktail mix rests beside the glasses, surrounded by textured placemats. Lush greenery provides a natural backdrop.

4.89 out of 5 average rating, 123 reviews

Quiet Yet Close/Steps to Pool/Paths, Pet Free Home

FamilyIndoor spacesBathroom

4.99 out of 5 average rating, 73 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

FamilyIndoor spacesLocation

5.0 out of 5 average rating, 21 reviews

UFO - Unique Forest Outpost with Hot Tub

FamilyIndoor spacesLayout