Surrender Completely to Luxury at the Top Rated Inn in the U.S.
5
Surrender Completely to Luxury at the Top Rated Inn in the U.S.
5
BOOK NOW
BOOK NOW
The Basics
SELECT REGISTRY MEMBER SINCE 2017
Jail Hill Inn is a boutique luxury inn located one block from downtown historic Main Street, prominently situated overlooking Galena and its stunning countryside. This 140-year-old building once served as the county jail for nearly 100 years. Each of the six suites is unique and includes a sitting room, wet bar, fireplace, king-size bed, Smart TV, Bluetooth sound system, and full spa-like bathroom with a luxurious steam shower or bubble-massage tub.
In the Know
Walk or bike down the Galena River Trail, which can be easily accessed from the property.
Galena is quickly becoming a top golfing destination. Each of Galena's 10 golf courses offers something different.
Go hot air ballooning and see Galena from an entirely different vantage point!
Visit the historic Ulysses S. Grant home or other historic attractions such as the Belvedere Mansion and Gardens
Stay for the Story
This historic inn, once an actual county jail in the 19th century, has been transformed into a refined and elegant retreat. The inn's architecture and interior design pay homage to its storied past, blending seamlessly with modern comforts.
Sip & Savor
Here are a few things to sip & savor when you visit…
Enjoy incredible food and the feel of a French bistro at Fritz & Frites
Galena's Fried Green Tomatoes restaurant serves the finest USDA Choice Steaks, Fresh Seafood and boasts a Wine Spectator Award Winning wine list
Sip award winning wines at Galena Cellars Winery
See & Do
Here are a few things to see & do when you visit…
Go shopping at the 100+ independent boutiques on Main Street in Downtown Galena. It's within easy walking distance of Jail Hill Inn
Go wine tasting at Galena Cellars, Massbach Ridge, Rocky Waters, Fergedaboutit Winery, Jamie's Wine Studio, The Grape Escape, or Champagne on Main
Take a trek and play with the goats! Our friends at Hoof It Galena offer a wonderful escape from the ordinary
Guest Reviews
Jail Hill Inn is absolutely incredible! The building is stunning, the rooms are spacious and luxurious, and every detail feels carefully thought out. Breakfast was gourmet and delicious, and the evening wine and cheese reception was such a nice touch. The location is perfect — close to downtown Galena yet quiet and private. The staff truly go above and beyond to make your stay unforgettable. Easily one of the...See More
- Al Hebron
If you have ever wanted to feel a small bit like royalty, this is the stay for you! The suites are all so intricately, interestingly, incredibly adorned and decorated in their own individual theme. The showers, whirlpool tubs, and amenities are amazing. The bed is like sleeping on a cloud. Don't get me started on the breakfast and wine trays....you won't need lunch after the delicious 3 course breakfast....See More
- Kelly Finck
My wife Laura and I had an absolutely incredible experience at Jail Hill Inn. The renovation of the historic jail is nothing short of stunning—every detail has been thoughtfully designed, blending charm and luxury seamlessly. Our room was extremely spacious, beautifully appointed, and incredibly comfortable. The location is perfect—just a short walk to all the shops and restaurants in downtown Galena, yet tucked away enough to feel peaceful and...See More
- Jason S
Absolutely loved our stay at Jail Hill Inn. Mathew is a remarkable host, and every detail is thoughtfully designed. The suites blend historic charm with modern luxury, and the three-course breakfasts were unforgettable (and even gluten-free friendly for my wife). Evening wine-and-cheese trays were a perfect touch. Peaceful setting just a short walk from downtown Galena. Truly deserving of being rated #1 in the U.S.—a hidden gem!
- Steve Hunt
There are good reasons that the Jail Hill Inn is one of the top B&Bs in the world. Matthew and his staff do an incredible job from the moment you arrive to the time you say 'See you again!' and you will absolutely want to see Matt again! The rooms are all unique and have their own charm, the 3-course breakfasts and wine & cheese hour will keep you...See More
- Kevin Meier
Rooms & Suites
# of Rooms: 6
Room Amenities: Air Conditioning, Bathrobes, Hair Dryer, Alarm Clocks, Antique Furnishings, Featherbeds
For information on ADA accessibility for the facility or its rooms, please contact the property directly.
Policies
Smoking Policy: Outside Only
Family Friendly: No
Learn moreFrequently Asked Questions
Does Jail Hill Inn in Galena, IL offer free parking for guests?
Yes, we offer free onsite parking.
Are spa services like massage available during a stay at Jail Hill Inn?
Yes, spa service is available.
Can Jail Hill Inn accommodate dietary restrictions for breakfast?
Yes, we accommodate special diets.
Is breakfast included at Jail Hill Inn in Galena, IL, and what kind of breakfast is served?
Yes. Each morning features a homemade, gourmet breakfast.
What room features are offered at Jail Hill Inn in Galena, IL (fireplaces, soaking tubs, porches)?
Suites feature king beds, sitting rooms, fireplaces (some rooms), spa-like bathrooms with steam showers or bubble-massage tubs; amenities include air conditioning, bathrobes, hair dryers, cable TV, and more. Some rooms include jetted tubs, microwaves, refrigerators, and private decks.
Does Jail Hill Inn have a restaurant, bar, or lounge onsite?
No, we don’t have a restaurant or bar onsite.
What are the best nearby restaurants for lunch or dinner close to Jail Hill Inn in Galena, IL?
Here are a few favorite local spots near the inn:
• Enjoy incredible food and the feel of a French bistro at Fritz & Frites
• Galena's Fried Green Tomatoes restaurant serves the finest USDA Choice Steaks, Fresh Seafood and boasts a Wine Spectator Award Winning wine list
• Sip award winning wines at Galena Cellars Winery
Are pets allowed at Jail Hill Inn in Galena, IL?
No, pets are not allowed.
Is Jail Hill Inn family-friendly, and do you allow children?
No, we’re adult-only.
How many guest rooms or suites are at Jail Hill Inn in Galena, IL?
6 suites.
What makes Jail Hill Inn unique compared to other places to stay in Galena, IL?
This historic inn, once an actual county jail in the 19th century, has been transformed into a refined and elegant retreat. The inn's architecture and interior design pay homage to its storied past, blending seamlessly with modern comforts.
Is Jail Hill Inn in Galena, IL accessible for guests with disabilities?
Accessibility is limited.
Does Jail Hill Inn support sustainable travel (eco-friendly practices, EV charging)?
Yes. We’re eco-friendly and offer EV charging (Standard and Tesla).
Can you host weddings, elopements, or private events at Jail Hill Inn in Galena, IL?
Yes. We host ceremonies, elopements, and private parties; meeting space is available.
What are the top attractions near Jail Hill Inn in Galena, IL?
Guests often ask about nearby attractions. Here are some highlights:
• Go shopping at the 100+ independent boutiques on Main Street in Downtown Galena. It's within easy walking distance of Jail Hill Inn
• Go wine tasting at Galena Cellars, Massbach Ridge, Rocky Waters, Fergedaboutit Winery, Jamie's Wine Studio, The Grape Escape, or Champagne on Main
• Take a trek and play with the goats! Our friends at Hoof It Galena offer a wonderful escape from the ordinary
Insider Tips:
• Walk or bike down the Galena River Trail, which can be easily accessed from the property.
• Galena is quickly becoming a top golfing destination. Each of Galena's 10 golf courses offers something different.
• Go hot air ballooning and see Galena from an entirely different vantage point!
• Visit the historic Ulysses S. Grant home or other historic attractions such as the Belvedere Mansion and Gardens
How far is Jail Hill Inn in Galena, IL from the nearest major city or airport?
The nearest airport is Dubuque Regional Airport (DBQ), about 15 miles away. Madison, WI is about 69 miles away. Chicago, IL is about 148 miles away.
Food & Wine
Meals Offered: Breakfast
Special Diets Accommodated: Yes
Restaurant on Premises: No
Dining Amenities: Complimentary Afternoon Tea/Refreshments, Complimentary Beverages, Complimentary Early Coffee Tea, Complimentary Evening Hors d'oeuvres, Complimentary Snacks, Evening Cocktails, Special Diets Accommodated
Guest Services
Internet Service: Wireless
Front Desk/Security: Onsite
Corporate Rates: No
Inn Amenities: Hot Breakfast, Concierge Services, Free Onsite Parking, Full House Rental Available, Gardens on Property, Green Environmentally Friendly, LGBTQI+ Friendly, Meeting Space Available, National Historic Registry, Spa Service, Weddings & Events Available, Wine/Spirits Available
Weddings & Celebrations
Wedding/Reception/Event Facilities: Indoor, Outdoor
Events Supported: Private Parties, Ceremonies, Elopements
Business Travel & Meetings
Meeting Types: Retreats
Meeting Facilities: Yes
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