Holiday rentals with a kayak in Jo Daviess County

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. )

Riverview Ranch & Resort - 3 BR, 2 BA Apt.

Comfortable 1300 sq. ft. 3BR - 2BA apartment in 24,440 sq. ft. equestrian resort. Meet horses, miniature horse, goat, pig, dogs, ducks, chickens, & guinea pigs up close and personal. Petting Zoo Tour included ($95 value). Pony rides and canoe/kayak tours available. Riverview sunsets, campfires. Nature hiking nearby. Full Kitchen. AC, TV, air hockey, billiards/ping pong, 2 King beds. So many things to do-all year long. Live music on request, when available. Fine Dining & Family activities nearby.

Secret Room-Fireplace-Hot Tub-Pool/Marina,Patio

Enjoy this gorgeous, huge home for your group getaway! Relax in this tranquil wooded setting with a private hot tub or soak in the luxurious tubs. Hang out in the "Secret" room with motorcycle bar & TV, drink coffee in 3 seasons room 4bed/4.5 bth home is spacious with multiple spaces to enjoy loved ones! Access to community indoor pool and seasonal outdoor pool Great perks like snowcone maker cottoncandy maker, axe throwing, ping pong, billiards, arcade game, Connect 4 and more. Dogs welcome

Lakefront cabin in the woods.

This stylish place has Wifi /Wood Fireplaces, Fully Stocked Kitchen, Coffee Maker, Washer/Dryer, Rear deck w/charcoal grill. 204 feet of lakefront property. Safe swimming off the pier & hunting for crawfish along the shoreline. Acres of woods to explore on property as well as 13 mile trail system around the Lake. Outdoor fire pit & With your stay is access to the swimming pool/tennis court, work out room, golf course (fees not included), Marina/Nixon beach. Don't forget to visit the waterfall!

Fun custom waterfront floating cabin-HOT TUB!

This newly built floating cabin sits on the backwaters of the Mississippi River. It’s 1970s mod design is unique and fun! This rental has 2 bedrooms with queen beds and a queen pull out couch. There is a full bathroom and a stocked kitchen. Soak in the hot tub and take in the waterfront views all around. While there are other cabins around, you have your own walkway and no one connected to you! Enjoy a kayak ride, fish, or just relax on your floating deck. This is located at Millennium Marina.

Hot Tub and Firepit at Beautiful Summer Retreat

Experience the ultimate family vacation, friends gathering, or romantic escape in our beautiful cabin! With 4 elegant bedrooms, each boasting an ensuite, and 4 patios (3 accessible from bedrooms), plus a spacious 3-season room, privacy and comfort are paramount. The cabin has been tastefully renovated to ensure an unforgettable stay. Nestled in the picturesque, resort-like Galena Territory, enjoy many amenities (pools, tennis courts, gym, game room, etc.) while only a 12 min drive to downtown.

Inviting & Bright | Firepit Sauna Hot Tub & Games!

Golfer? Inquire for(e) for details on our Golf Packages. Welcome to The Overlook, your perfect home away from home during the upcoming summer season in the Galena Territory. This contemporary three-bedroom, two-and-a-half-bathroom home is the ideal retreat for a relaxing and fun-filled vacation. Enjoy the firepit under starry skies, sweat it out in the sauna, soak in the hot tub, or challenge your friends to Pac-Man or foosball. Perfect for families and couples alike. Dog-friendly with a fee.

Family Friendly Modern Farmhouse 42 Private Acres

PRIVATE FARM FOR YOU! 42 acres of woods, prairie and pastures surround a renovated 1880s farmhouse nestled in a private valley outside Elizabeth, IL. Breathtaking views, fishing pond, canoe, hiking trails, fire pits, screened in porch and acres of rolling prairie make for the perfect getaway. Pets welcome (add. fee applies). 20 min. from Galena & 2 hrs from Chicago. Family friendly, we provide everything for kids of all ages including pack-n-play, height chair, games, activities and more.

Charming 3B3B | Access to indoor and outdoor pools

Discover comfort and charm in our inviting 3-bedroom, 3-bathroom home nestled in the heart of the Galena Territory. Immerse yourself in the tranquility of nature while enjoying modern amenities. This spacious retreat features a fully-equipped kitchen and cozy living areas with a fireplace and arcade. Explore nearby hiking trails, golf courses, and historic downtown Galena. Whether you're seeking relaxation or adventure, our Galena getaway is the perfect home base for an unforgettable escape.

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

Cozy, Private Retreat with Hot Tub & Firepit Welcome to The Nest—a cozy, peaceful escape tucked into the woods of The Galena Territory. ✔ Spotlessly clean, peaceful wooded setting ✔ 3 bedrooms & 3 bathrooms — ideal for groups • ✔ Private Hot tub • Fire pit • Dog-friendly ✔ Discounted golf available at Eagle Ridge ✔ 12 minutes to Downtown Galena ✔ Access to Galena Territory Amenities • Indoor/Outdoor pool • Fitness Center • Pickleball • Lake Galena & Marina • Shenandoah Riding Center

The Tree House

Escape to The Tree House, a cozy & secluded 1-bedroom retreat nestled at eye level with the trees. Perfect for couples, this peaceful hideaway offers a king bed in the master and panoramic forest views from every room. Relax in nature with your own private sauna and fire pit, both overlooking wooded surroundings. We are in the middle of the woods - please note to expect hiking paths, animals, bugs, & weeds. City expectations vs. the woods are different. Please inbox with questions!

C&R Lake Lacoma

Keep it simple at this peaceful and centrally-located home on Lake Lacoma in East Dubuque. Sleeps up to 4 . Has 2 bedrooms, 1 with king size bed and the other has a queen size bed. Each bedroom has a TV. 1 bathroom with tub, shower, washer and dryer. Enjoy the outdoor scenery on the 800 sq. ft. wraparound deck. Spend time fishing, playing horseshoes or relaxing by the fire pit. Galena, IL approx. 10 miles and Dubuque is approx. 1 mile. No indoor smoking. No pets.