Holiday houses in East Galena

Cozy retreat in Galena Territory

Charming 2-bedroom 2-bath townhome each having king size beds and an ensuite bath nestled in Galena Territory, just 12-minute drive from downtown. Featuring spacious bedrooms, baths and fully equipped kitchen. This cozy home nestled on the Eagle Ridge South Course, walking distance from the pro shop. Access to the owner's club which has a fitness center, indoor & outdoor pool, game room, pickle ball and tennis courts. Enjoy the convenience of nearby amenities while savoring residential area.

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.

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!

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.

Ulysses Suites, Suite 202

Ulysses Suites has just been completed inside the historic J. G. Schmohl building in the heart of downtown Galena, located at 213-217 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 202 is a gorgeous studio with a huge window seat looking over Main Street.

Fireplace Apartment Main Street Galena

Step into the history of Galena and enjoy this fully-renovated apartment, located inside Galena’s historic Logan House Hotel! This apartment features exposed original brick, and hardwood floors, and boasts a cozy feel. Conveniently located right atop of Big Bill’s Coffee shop on the north end of Galena’s hoppin’ Main Street, the Fireplace Apartment is only feet away from restaurants, shopping, and night life! Check out all our listings at Airbnb.com/p/galenaIL( copy & paste into URL)

1842 Bavarian Brew House

Nestled in charming and historic Galena this beautiful home was built in 1842 by brewer Peter Specht from Bavaria. The cellar operated as his brewery and tavern while living in the home above. The house was extensively renovated in 2008. It remains full of character and charm, but now boasts an abundance of modern comforts. A quiet private patio and yard are the perfect spot for a morning coffee or a glass of wine. All within a few walkable blocks to Main Street, the heart of Galena!

Stagecoach Valley Getaway

Out in the country but only 1 mile from downtown Galena on historic Stagecoach Trail, this unique lodging experience offers a peaceful setting in the heart of the valley - surrounded by hills, woods and abundant nature. Spend quality outdoor time on the large deck overlooking the fire pit and Stagecoach valley. The house is comfortably and tastefully furnished with a spacious, open floor plan with a full kitchen, 2 large bedrooms, 2 full bathrooms and a large enclosed porch.

Suite Victory #4 On Main St w/Reserved Parking

Suite Victory #4- Beautifully renovated apartment on Main St. right where you want to be with Reserved Parking. Dining, entertainment, and shopping just outside your door. Open floor plan with beautiful views of downtown Main Street. King bed. Double sink vanity and large walk-in shower. Kitchen has island, quartz countertops, and new appliances. Stackable washer and dryer within the unit. Above Charlie’s Place Eatery on Main Street. MAX 2 PEOPLE. NO PETS ALLOWED.

Gameroom in Galena

In the center of downtown Galena, we offer over 1500 sq ft. in a 1852 building. A bay window offers 180° view of Main St. A pool table, shuffleboard, pinball machine and bar are at your disposal. You'll have access to either Main Street from the front or Bench Street from the back. There is free parking on South Main Street and out the back on South Bench Street. There is no dedicated parking spot but parking opens up quit a bit in the evenings.

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

Dawson's Remise Luxury Accommodation

Enjoy a luxurious stay in our remise ("carriage house"), complete with authentic Art Deco and Industrial furniture and design. We took great care in ensuring top notch craftsmanship and amenities, so as to create an inviting environment that you won't want to leave! Hidden away off the quaint and historic Park Avenue, you'll enjoy a quiet and restful stay whilst within walking distance to Main Street Galena and all it has to offer.