Take your family on a memorable getaway in Galena to enjoy a winter vacation. Located in Jo Daviess County in the northwest part of Illinois, this magnificent city is home to historic buildings, award-winning restaurants, and the finest wineries. If you want to see something interesting, head to West Street Sculpture Park and PT Murphy Magic Theater. What’s more, this city has accommodations that offer easy access to skiing opportunities. If you are planning to ski in this city, make sure you book the right place that will keep you warm and comfy after a day of fun-filled activities. Read on for the top ski resorts in Galena, Illinois.
We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to ski slopes and equipment. The image galleries get refreshed with the latest updates regularly. They were last updated on October 28, 2025.
1. Chestnut Mountain Resort (from USD 119)
Chestnut Mountain Resort is one of the premier ski spots in the city. Situated close to the downtown area, this ski resort boasts a 20,000-square-foot (1,858.1 square meters) ski facility with a 475-foot (144.8 meters) vertical drop that spans 3,500 feet (1,066.8 meters) across 19 runs. Its longest run is 0.7 miles (1.1 kilometers). The exceptional ski area comprises four triple chairs, two quad chairs, one surface lift, and two conveyor lifts. If you’re a beginner, you may participate in the resort’s private lessons with the help of their 50 expert instructors. Season passes here start from 130 USD.
After skiing, you can make up for the calories you’ve burned by feasting on sandwiches and pizzas at the resort’s on-site restaurant. Resort amenities include free parking, free wi-fi, and an indoor pool.
Chestnut Mountain Resort
Address: 8700 West Chestnut Mountain Road PO Box 6328
29.57 km (18.4 mi) from National Mississippi River Museum & Aquarium
Other accommodations near ski area
2. Best Western Galena Inn and Suites (from USD 99)
Situated just 8 miles (12.9 kilometers) from Chestnut Mountain Resort, this 3-star hotel features modern rooms, 2 swimming pools, a shared lounge, free parking, and free wi-fi.
Once you’re here, you can start your day by relishing a fresh American breakfast right before you engage in fun activities in Galena, such as mini-golfing, horse riding, and off-site cycling and skiing. You can also keep yourself busy throughout the day by working out at the hotel’s state-of-the-art fitness center.
Best Western Galena Inn & Suites
Address: 9923 US 20 West
22.24 km (13.9 mi) from National Mississippi River Museum & Aquarium
3. Charming house with gas grill (from USD 256)
The three bedrooms in this 1842 house boast elegance and a cozy atmosphere, so you should consider staying here if you want a remarkable vacation in Galena. This tastefully remodeled vacation rental for six includes convenient amenities, such as a gas grill, free wi-fi, central air conditioning, a TV, and laundry essentials. It also has a full kitchen that includes dishes, utensils, an ice maker, a stove, a microwave, and a refrigerator.
What’s more, this vacation house is just 6.7 miles (10.8 kilometers) from Chestnut Mountain Resort, one of the most-visited ski destinations in the city.
Galena, Illinois, United States
20.75 km (12.9 mi) from National Mississippi River Museum & Aquarium
Top guest reviews
Host:
angela and mike are very responsive to any questions or concernsrented the property for a wedding weekend - it was awesome and mike & angela are great hostsLocation:
nice place liked it a lotCleanliness:
it is clean spacious beautiful and uniqueRead more reviewsAmenities & Room:
the outdoor seating area was perfect place to catch up with the gas fire pit table and lights
4. Galena RowHouse (from USD 349)
This property is a fantastic vacation rental where you can spend a weekend with your loved ones. With its expansive four bedrooms, two and a half baths, and well-stocked kitchen, this homey property will lift your stay to new heights. It is also an ideal place for those who want to ski because it is just less than 20 minutes from Chestnut Mountain Resort.
While you may enjoy an inspiring morning at the patio, which comes with scenic views, your nights will surely be restful, thanks to the comfy beds and quality linens. Other amenities here include a fireplace, air conditioning, heater, parking, and internet access.
Galena, Illinois, United States
21.06 km (13.1 mi) from National Mississippi River Museum & Aquarium
Top guest reviews
Host:
Hosts were wonderful answering our few questionsThe host was responsive and friendlyThe owner was friendly and helpfulWe appreciated the history of the home and what the city had to offershe made everything very easyLocation:
Property very nice and within walking distance of activities shoppingThe location was perfect and close to all shops and restaurants I would definitely recommend this house to anyone wanting to stay in Galena and be close to Main StreetThe Galena Row House is the perfect place to stayWe had a great time in Galena and a very comfortable house to stay inWe absolutely loved this house and the locationCleanliness:
wifi ample towels and hot waterEverything was very easy and the location was absolutely perfectbut I'm sure it was common in the 18th century )Read more reviewsAmenities & Room:
held shower on 4 th floor Very comfortable in all regardswhen running Could use better window shades in the front bedroom facing the streetetcCould use another shower or curtain around tub and handThere was more then enough room for 8 peopleWe only wish that there was more then 1 shower
5. Irish Cottage Inn and Suites (from USD 159)
Hotel Irish Cottage Inn and Suites is just around (14.9 miles) 24 kilometers from Dubuque Regional Airport. This hotel boasts a variety of facilities that ensure guests’ comfort. These amenities include a swimming pool, a spa, a wellness center, an in-house dining option, and free parking. There are several rooms here that are suitable for a family or couples aiming for a romantic vacation. Rooms are fitted with a flat-screen TV and tea or coffee-making facilities.
Hotel Irish Cottage Inn and Suites is perfect for ski enthusiasts, as Chestnut Mountain is just 9 miles (14.5 kilometers) away.
Irish Cottage Inn & Suites
Address: 9853 US Highway 20
22.44 km (14.0 mi) from National Mississippi River Museum & Aquarium
6. Goldmoor Inn and Resort (from USD 400)
Delicious dinner at the restaurant, outstanding breakfast served in-room, and fabulous evening meals.
Pricier than other options in the area, but worth the splurge for the beautiful facilities and exceptional service.
Secluded, picturesque setting with great views, about 15 minutes from downtown Galena.
Electric vehicle charging, spacious rooms with jacuzzi tubs, and breakfast delivered to the room each morning.
With innumerable conveniences and wonderful views, this property is a great choice if you are planning to go skiing on your next vacation. Goldmoor Inn and Resort offers a spa and wellness center, a hot tub, an in-house restaurant, a garden, and free private parking. As for accommodations, the rooms here are fitted with a dining area, a kitchenette, a flat-screen TV, and a private bathroom.
Chestnut Mountain is just 2 miles (3.2 kilometers) from here, so if you’re skiing, snag your ski pass from this resort. For an extra fee, you can make use of the ski storage on site.
Goldmoor Inn & Resort
Address: 9001 North Sand Hill Road
28.29 km (17.6 mi) from National Mississippi River Museum & Aquarium
7. Vibrant house with patio (from USD 351)
This modern and exquisite vacation rental is a great choice if you’re eyeing a memorable ski trip at Chestnut Mountain Resort. The said ski resort is approximately 6.3 miles (10.1 kilometers) from this property. There are also golf courses and a horseback riding center nearby.
The house can accommodate up to eight guests, and it has a fully furnished kitchen, a dining table for six, and a furnished patio. You can also make use of other amenities, such as air conditioning, laundry facilities, a fireplace, and a parking space.
Galena, Illinois, United States
30.85 km (19.2 mi) from National Mississippi River Museum & Aquarium
Top guest reviews
Host:
the owner was very gracious and welcoming- would definitely recommend this houseLocation:
the house was wonderful and provided the perfect location for our familyCleanliness:
the house was beautiful clean comfortable and included everything we neededvery nice house it was super clean and had all the essentials needed for a stayit was very clean and all the instructions were easy to understandthe location is beautiful and the home is very clean and brightRead more reviewsAmenities & Room:
there was space for eight of us to be comfortable for family time and alone time
8. Aldrich Guest House (from USD 174)
Scrumptious and beautifully presented breakfasts, delicious cocktails, and accommodating hosts for special dietary needs.
Reasonable pricing for luxurious accommodations and delicious breakfasts.
Walking distance to Visitor’s Center, Grant Park, Trolley, Belvedere Mansion, and other attractions in Galena.
Beautifully decorated rooms with comfortable beds, toiletries, and a central location within walking distance to attractions.
Before or after you go skiing in Chestnut Mountain Resort, be sure to stay in Aldrich Guest House. Located 8 miles (12.9 kilometers) from the ski resort, this gorgeous property boasts well-appointed rooms that have a private bath and air conditioning. As for shared facilities, it comes with a lounge and free parking. Free wi-fi is also accessible here. During your stay, a complimentary breakfast is included in your rent. The breakfast choices are either American, vegan, vegetarian, or gluten-free.
The location of this rental is fantastic, as it would only take you five minutes to walk to Main Street Galena. This means you can easily reach great dining and shopping options.
Aldrich Guest House
Address: 900 3rd Street
21.48 km (13.4 mi) from National Mississippi River Museum & Aquarium
9. The Federal House (from USD 178)
Situated around 15 minutes from Chestnut Mountain Resort, The Federal House is a fabulous bed and breakfast accommodation in Galena. For added convenience, ski equipment rental is offered here.
The property comes with facilities for barbecuing, free private parking, an outdoor fireplace, a patio, and free wi-fi. Daily housekeeping and concierge services are also available. All rooms include a flat-screen TV, a microwave, a fridge, a seating area, and a private bathroom with a shower. For an additional charge, you can stay here with your pets.
The Federal House
Address: 603 South Bench Street
21.09 km (13.2 mi) from National Mississippi River Museum & Aquarium
Great winter activities await you in Galena
With several spots for skiing, snowboarding, or snow tubing, Galena is the perfect destination for winter lovers, especially those who love sports. For your accommodation needs, make sure to stay in one of these options in Galena, Illinois, for a convenient time.
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