Holiday houses in Lake Galena

Doe Meadow, a tiny house farm stay

Doe Meadow is my newest custom designed tiny house nestled along the drive to my family farm. Sharing my little slice of heaven with guests is something I have found great joy in. Rural tourism is my passion, & all the farm animals are anxiously awaiting your visit- treats in tow- of course! I wanted to create something unique, a place to make memories, & somewhere you'll want to come back to. Settle in the hammock, listen to the peaceful wind chimes, watch the goats & mini cows graze, unwind.

Lux|Chic|Instaworthy|Fireplace|Cable |Near Ski

Are you seeking a stylish and tranquil escape in the countryside? Our fully renovated and modernized townhome is the epitome of luxury and comfort, ensuring a memorable stay. Situated in the picturesque, resort-like Galena Territory, surrounded by lush hills and with access to a plethora of amenities(e.g., pools, tennis/pickleball courts,gym,game room), our home offers a peaceful retreat while being conveniently close to downtown, golfing, wineries, breweries, dining, shopping and ski (Chestnut)

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.

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.

Pleasant View School

Welcome, this beautifully renovated schoolhouse, now a cozy and quaint 2-bedroom, 2-bathroom home, is perfect for couples, families, or friends looking for a unique stay. Step inside and enjoy the perfect blend of historic charm and modern comfort. Relax by the fireplace after a day of exploring, soak in the private hot tub under the stars, or cook a delicious meal in the fully equipped kitchen. Outside, unwind on the patio with your morning coffee or evening drink by the warmth of a fire.

Lake Views | Hot Tub | Nature Retreat | Movie Room

Looking for nature? Come immerse yourself in nature at this private oasis. • 3 bed/3.5 bath (7 adults comfortably w/max 8 guests) • 12 mins to downtown Galena • Outdoor hot tub • Grill & dining space on upper deck • Seasonal views of Lake Galena • Lounge/Movie room with pool table, electric fireplace & smart TV • Full Kitchen w/fridge, oven, microwave, dishwasher, keurig coffee machine, air fryer, instant pot, & crockpot • Upstairs family room with smart TV, fireplace, & board games

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

Family Fun! Hot Tub•Fire Pit•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

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

Mirror Lake - Rare private lake!

Create amazing memories at Mirror Lake Vacation Retreat, a breathtaking 13-acre private estate, featuring your very own 3-acre private lake, complete with lakeside amenities like a sand beach, dock, kayaks, peddle boat, fire ring, and gazebo. Oh, plus there's the 4,500 ft2 custom home with multiple porches, an 8-person outdoor hot tub, huge yard, walking trails, and a stand-alone game cottage complete with a pool table, shuffleboard, ping-pong, air hockey, and more!

King Loft | Fireplace | Arcade Game | Pool Access

Escape to this cozy 1-bedroom cottage retreat in The Galena Territory—perfect for slowing down, reconnecting, and enjoying everything Galena has to offer. ✨ HIGHLIGHTS • King loft bedroom with skylight ✨ • Wood-burning fireplace 🔥 • Retro arcade game + puzzle collection 🎮 • Access to Owner’s Club (pool, fitness center & more) • Fast WiFi • 12pm check-in & check-out • ~10–15 minutes to downtown Galena • Cozy, romantic cottage feel

The VIP Room at The Cathouse Suites, Dogs OK w/$$

Newly renovated building in historic, Uptown Galena above Miss Kitty's Grape Escape. One studio apartment with kitchenette with microwave and coffee/kcup maker, queen size bed (not a futon), 4K TV, & Wheelchair accessible patio. Extra mirrors in the bathroom with a full size shower, bathrobes and lush towels. Easy access to premier night life and entertainment just below at Miss Kitty's Grape Escape.