Family-friendly holiday rentals in Jo Daviess County

Mississippi River house has everything you need

Your family will be close to everything when you stay at this centrally-located place. The river is right across the street and so is the walkway the walkway will take you all the way to the other end of town beautiful walk along the river. Richmond‘s café Great place for breakfast. The brewery has igloos to sit in outside just two blocks from the guest house. The river park will be lighted for Christmas right across the street all the way through the end of town Great place to be this holiday

Winter Fun! Hot tub-Fires in/outdoor-Game room!

Escape to our cozy luxe cabin in Galena Territory, the perfect retreat for fall! Start your mornings sipping coffee by the gas fireplace, then warm up each evening in the hot tub! Enjoy friendly competition with arcade games, board games, air hockey, and darts. With 10 amenity cards, you can access the owner’s club for swimming and exercise including indoor pickle ball-rackets and balls at the house! Experience relaxation and adventure in this tranquil haven—your unforgettable getaway awaits!

Creekside Cottage farm stay nice for two to six.

Relax and enjoy time together at Creekside. The cottage is a picturesque spot for one or two guests or for groups up to 6. Extra guest charge is $20 per person after 2. Located on our farm only 15 minutes from downtown Dubuque and the Mississippi Riverfront. Explore the woods, fields, and creek on our farm. Visit the animals. A short drive to Mines of Spain, EB Lyons Nature Center, Eagle Point Park, Galena, Bellevue, Chestnut and Sundown ski areas, two monasteries, craft breweries, wineries.

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.

Pet friendly, 2 BR close to Mississippi River

This comfortable home is a 2 BR 1 BA with a full kitchen, and off street parking. It is 1 block away from the Mississippi River and within walking distance to local shops, restaurants bars, parks, and walking trails. The local grocery store is located directly across the street. Well behaved pets are welcome. The backyard is completely fenced in. NO SMOKING INSIDE. As stated in the other notes section, we are located along the Canadian Pacific Railroad and there will be trains going by.

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

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

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!

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

Relax with the whole family at this peaceful getaway. A beautifully renovated, 3 bedroom / 3 bathroom townhome located within The Galena Territory in Galena, Illinois. This home is a perfect, peaceful getaway that sleeps up to eight (8) people comfortably. Whole home Golf Lake Self Check in WiFi Coffee Oven Dishwasher Grill BBQ accessories Washer/Dryer Free parking Board games Exercise equipment Pool table Deck Outdoor dining Child friendly Pack 'n play Pickleball set

Perfect Location! Owner Club Access, Steps to Pool

Cozy Tranquility on Walnut, Galena IL Entire Home Vacation Rental, 1 Bed, 2 Bath, 4 Person Occupancy This adorable, recently remodeled and refurnished, 1 bedroom/2 full bath townhome is ready to welcome and embrace you any time of the year! Situated with seasonal views of the North Golf Course, and just a short distance from the driving range makes it a great choice for golfers... it's charm and central location make it an ideal choice for everyone!

Aspen House - A Secluded Getaway In Nature

Relax with your loved ones at the peaceful Aspen House. A Miner's Cottage nestled in a beautiful stand of aspen trees = a quiet retreat just for you! The property is surrounded by protected wooded green space with the Taylor Run trail adjacent on the northwest side. The Owners Club, pools & lake are accessible by hiking/ 5 minute drive. Enjoy bird watching, fishing, hiking and picnicking without driving anywhere!

Hot Tub + Fall Views | Peaceful Escape

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.