Family-friendly holiday rentals in Jo Daviess County

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Top-rated family-friendly rentals in Jo Daviess County

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite

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.

Home in Galena

4.93 out of 5 average rating, 222 reviews

Galena Getaway

Peaceful, pet-friendly ($50 fee per reservation) vacation home in the Galena Territory. 3 bedrooms, 3 bathrooms, two living rooms, 2 wood fireplaces, screened in porch, upper level porch, deck, firepit, access to owner's club (pool, exercise room and game room), marina and 24 miles of hiking trails. Sleeps up to ten people. (Please ensure your guest count is accurate when you make your reservation. The guest count can be updated if needed. Inaccurate reservations will be charged accordingly. )

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Top Guest favourite

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.

Home in Galena

4.96 out of 5 average rating, 137 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

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Top Guest favourite

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.

Cabin in Galena

4.96 out of 5 average rating, 140 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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Top Guest favourite

Cabin in Elizabeth

4.98 out of 5 average rating, 139 reviews

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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Top Guest favourite

A spacious living area features vaulted wood ceilings and a stone fireplace, creating a warm focal point. Cozy seating arrangements include plush sofas and armchairs, accompanied by decorative blankets. Large windows allow natural light to flood the space, showcasing wooded views outside.

Cabin in Galena

4.98 out of 5 average rating, 200 reviews

Family Fall! Hot Tub•Fire In/Out•Game Room•3 Kings

Relax, unwind, & explore at this Fall Retreat in Galena Territory! Escape to this cozy, spacious cabin for a peaceful winter getaway. Sip morning coffee as snow falls through the trees, then unwind in the hot tub or by the fireplace. Roast marshmallows around the fire or enjoy arcade games, air hockey, darts, and more indoors. Stay active with access to the owner's club—indoor pool, fitness center, and pickleball (8 amenity cards included). Perfect for relaxation and fall/winter adventure!

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Top Guest favourite

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.

Home in Galena

4.97 out of 5 average rating, 133 reviews

Secluded Treehouse w/great views from every room!

Enjoy the many charms of this one of a kind Tuscan style treehouse with different levels showcasing spectacular views. This home has every amenity and personal touch of home to make your stay relaxing and memorable. Conveniently located approximately 1 mile off Highway 20 in the Galena Territory, backing up to hole 13 on The General Golf Course. Set back off the main road you will enjoy privacy without sacrificing convenience and access to the many amenities offered during your stay.

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Top Guest favourite

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

4.99 out of 5 average rating, 241 reviews

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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Guest favourite

Home in Galena

4.94 out of 5 average rating, 282 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

Welcome to the Toasted Marshmallow; your cozy escape from reality. Enjoy the peace and quiet of this charming three bedroom, two bath home in The Galena Territories. Kitchen is fully equipped to meet your needs. Enjoy the additional lower level family room w/ 2nd fireplace so your group may spread out. Deck with ample room for dining outside and enjoying your coffee or wine. Home includes six access passes to the GTA Owner's Club and pools. Strong Wi-Fi for remote work, if needed.

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Top Guest favourite

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

4.93 out of 5 average rating, 394 reviews

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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Guest favourite

Cabin in Galena

4.88 out of 5 average rating, 129 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.

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Top Guest favourite

Home in Galena

5.0 out of 5 average rating, 101 reviews

5 Min to Owners Club | Hot Tub & Bunkhouse

Escape to the idyllic charm of our 5-bedroom Cottage, tucked in the beautiful Galena territories. Prime location within minutes of the Owners Club (free access) & Eagle Ridge Resort where you can enjoy all of their public amenities. From the inviting warmth of the interiors to the large, covered deck overlooking the open backyard and the hot tub on the patio, every feature of our rental promises a unique and unforgettable escape.

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Top Guest favourite

A spacious kitchen features a large island with four stools and sleek cabinetry. Modern stainless steel appliances are showcased, along with a stylish tile backsplash. Natural light streams in through a window, highlighting the open design that connects to the adjoining living area.

Home in Galena

4.96 out of 5 average rating, 156 reviews

Summer Escape in Galena | Hot Tub & Relax

Welcome to Pine Ridge—a peaceful, modern 2-bedroom, 2.5-bath vacation rental in The Galena Territory. With two king suites, a cozy living area, forest views, and a private hot tub, it’s perfect for couples, friends, or a remote work getaway. Relax on the porch, unwind by the fireplace, or explore nearby trails, shops, and GTA amenities. Just 5 minutes to the Owners Club and 10 minutes to downtown Galena.

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