Chestnut Mountain Resort

Stay at Chestnut Mountain Resort in Galena, IL; Dates into September

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Hotel at a Glance: Chestnut Mountain Resort

Illinois might not be the first place that springs to mind when you think of a mountain resort. Galena's Chestnut Mountain Resort is an exception. From the top of its namesake 1,020-foot peak, you can see clear through to two other states: Iowa and Wisconsin. In the winter, Chestnut's slopes are filled with snowboarders and downhill skiers, streaking down towards the Mississippi River. But when summer rolls around, visitors ride the chairlift to the top and sled down the mountain's 2,000-foot alpine slide.

  • The Great Outdoors: Explore five miles of hiking and biking trails on Chestnut Mountain
  • In-room amenities: Standard two-queen rooms come with a TV, free WiFi, sofa sleeper, and sitting area with table and chairs
  • Dig into fresh seafood, steaks, sandwiches, and pizzas at the Sunset Grille, perched atop a bluff that overlooks the Mississippi River Valley
  • Play a game such as miniature golf or disc golf, or rent a bike from the front desk
  • Make a splash in the indoor pool or soak in the hot tub
  • Segway tour: The resort offers Segway tours that explore the property's scenic terrain for 75-90 minutes.
  • Rolling on the river: Sign up for a 90-minute cruise down the Mississippi River, where you can look out for local wildlife (including the bald eagle), learn about local history, or just enjoy the river's famous beauty.

Galena, Illinois: Quaint Mississippi River Town with Historic Main Street

Galena is a relic from the mid-19th century, when it first boomed as a mining town and port city on the Mississippi River. Today, its quaint downtown historic district—which Fodor's praises as the "epitome of small-town America"—is lined with coffee shops, specialty boutiques, art galleries, and restaurants in 19th-century brick storefronts. Its Main Street even earned a spot on a Travel + Leisure list of "America's Greatest Main Streets."

History buffs should make a stop at Ulysses S. Grant's Home, where the 18th president and Civil War general lived after the war. Other popular pursuits include golfing at Eagle Ridge or touring wineries in the area.

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What You Get

  • Stay for two in a standard two-queen room
  • Up to four kids 6 or younger stay free
  • Dates into September

Policies and Fees

  • Reservations: Dates cannot be changed once booked; valid only for night(s) purchased.
  • Cancellation policy: 48-hour cancellation notice required prior to check-in or reservation is nonrefundable; reservations made within cancellation window are non-refundable
  • Rates may vary by date and are subject to availability.

No-shows will be charged total Groupon rate; no refunds, rescheduling, or rebooking allowed. Read the Fine Print for important info on offer details and other restrictions.


  • Restaurant
  • Hiking and mountain biking trails
  • Alpine slide
  • Miniature golf
  • Disc golf
  • Free WiFi

The Fine Print

  • Dates cannot be changed once booked; valid only for night(s) purchased
  • 48-hour cancellation notice required prior to check-in or reservation is nonrefundable; reservations made within cancellation window are non-refundable
  • No-shows will be charged total Groupon rate
  • Traveler name must match ID at time of check-in
  • No refunds will be processed by Groupon after check-in
  • Must be 21 or older to check in
  • Credit card required at check-in.

Other Details

Room Details

Standard Two-Queen Room

  • Two queen beds and one sofa sleeper
  • Standard occupancy: 2
  • Maximum occupancy: 6
  • Adding occupants above standard: $11.10 per night for each additional guest 7 or older; guests 6 or younger stay free

Hotel Policies

  • Check in: 3 p.m.
  • Check out: noon
  • Parking: free
  • Rollaways: not available
  • Smoking policy: no smoking inside the property
  • Pet policy: pets are not allowed in valid Groupon rooms
  • Accessibility: please contact property for handicap accessibility requests or options.
  • Room upgrades: not available

Getting There

  • Nearest airport: Dubuque Regional Airport (DBQ; 31 miles)
  • Distance to Dubuque: 24 miles

Customer Reviews

3 Ratings

We loved the beautiful setting-- the woods and Segway tour!
Thomas L. · March 30, 2016
Great mountain for the Midwest. Well maintained. Clean rooms. Accommodating Staff. Fun environment & facility. Pet friendly. We will be back again next season!
Shane H. · April 1, 2015
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