Holiday rentals in Lake Galena

Pet Friendly/Beautiful Bluebirds/Star Studded Sky!

This darling, dog friendly, 3 bedroom, 3 bath home is located in an exclusive corner of The Galena Territory with beautiful landscaping and open space all around for yard games galore! The large welcoming front porch will soon become a common space to relax and have coffee while taking in the fresh Galena morning air. Our Bluebird House is close to downtown Galena and has access to all the Galena Territory Owners' Club amenities as well as the Marina and Shenandoah Riding Center. Come Join Us!

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.

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.

Updated Home, King 2 bdrm, Private, Firepit, Pools

Starfell Cottage is a recently renovated retreat surrounded by woods and professionally designed for slow mornings, real fires, and star-filled nights. This 2-bed, 1.5-bath cottage comfortably hosts up to four guests and offers a rare blend of luxury, privacy, and nearby resort amenities - just 5 miles from historic downtown Galena. Sit by the indoor wood fireplace and enjoy our board games. Have a bonfire in the woods and stargaze. Community indoor pool/seasonal outdoor pool/indoor gym!

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

Perfect Getaway: Newly Renovated

Take it easy at this unique and tranquil getaway. Relax with a few friends at this peaceful place to stay. Located in the Galena Territories, this rental provides something for everyone. During the summer months you can access trails, golfing, an indoor and outdoor pool and so much more. During the winter months you are close to one of the finest ski resorts around. In Fall, access breath-taking views of trees as they change color. All year round there is something to look forward to!

Ulysses Suites, Suite 203

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. Suite 203 is almost 1400 square feet and is located on the 2nd floor.

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

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

Cozy Galena Retreat | Trails, Pool & Eagle Ridge

This one bedroom condo is perfect for a relaxing getaway. It is centrally located to the spa, golfing, and the marina. It is in a quiet location that backs up to a wooded area. There are a number of surrounding trails with beautiful views of the lake. At the end of a day soak in the jetted tub or relax in a rocking chair on the back porch. The condo has everything you would need to feel right at home.

Beautiful Sunset Point! Arcade Game Table!

Keep it simple at this peaceful and centrally-located condo. 2 king bedrooms, 2 bath, sofa sleeper, WIFI, Lake views, Screened Porch, Small back deck, Streaming Tv's, Coffee bar, arcade game table, and private pool for Long Bay Condo guests. Access to resort amenities while you stay and a short drive to downtown Galena for shopping, fine dining, wine tours, trolley tours, and much more.