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!

Fast Wi-Fi | EV Charger | Fireplace | Hot Tub

Unwind in our comfortable Galena Territory cabin with 3 bedrooms, 3 full baths and sofa sleeper. EV Charging outlet in garage. Strong Eero boosted Wi-Fi; Roku streaming on every floor. Stone wood burning fireplace. Three-season room with scenic sunrise and wooded views. Lower-level walkout to patio with hot tub, fire pit and beautiful stargazing. Minutes away from the Lake Galena Marina, golf, tennis, pool, and fitness center. 15 mins from Chestnut Mountain and historic downtown Galena.

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.

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

2BR 2BA + 3rd BR loft lakefront townhome sleeps 6!

Enjoy everything Galena has to offer from this lovely 3-story, 2BR + 3rd BR loft 2BA townhome. Comfortably sleeps 6 with all the amenities of home. View of Lake Galena Oct-May. Golf, 31-miles of hiking trails & the Inn are nearby. 6 Owners Club passes provide access to indoor/outdoor pools, fitness center, game room, basketball & tennis courts are a short, 1 mile walk, run or drive away. Nearby marina offers fishing, bait, tackle, pontoon, canoe & kayak rental but, no swimming.

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

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.

Fireplace | Foosball | Pool Access | Deck

Escape to this cozy 2-bedroom + loft, 3-bath retreat in The Galena Territory—perfect for relaxing, reconnecting, and enjoying everything Galena has to offer. ✨ HIGHLIGHTS • Wood-burning fireplace 🔥 • Foosball • Access to Owner’s Club (pool, fitness center & more) • Smart TVs + fast WiFi • 12pm check-in & check-out • ~15 minutes to downtown Galena • Loft layout with 3 levels total

Newly remodeled Rustic Townhome small dogs welcome

Newly remodeled Cabin decor townhouse. We do allow small pets under 25 LBS to come along there is a fee of $50.00 per pet/per stay. Any pets larger than 25LBS must be approved otherwise there will be a fee of $250.00 per pet. No Cats allowed. 2 Bedroom, 2 Bath. Centrally located in the Galena Territories. Access to the Owners Club and just 10 minutes from downtown Galena.