Guest Houses

Guest Houses

One-of-a-kind Accommodations

Make your trip to Madison even more memorable with a stay in one of our one-of-a-kind guest houses! Make yourself at home in a stately two-story Italianate from the 1800s or a humble shotgun abode with top-notch accommodations. Looking for trip inspiration for your getaway to Madison? Check out our itineraries and our event calendar to see what’s happening during your stay!

Found 21 listings

General’s Quarters

Explore downtown Madison in these two separate homes. Each is 4 Bedrooms (2-Kings, 2-Queen) 3.5 baths, and includes dedicated parking. Both sleep up to [...]
207-209 W 1st Street, Madison 47250
Phone: 703-999-2053

Dugan Hollow Retreats

Four beautifully decorated private suites with modern amenities located just minutes from Historic Downtown Madison and Clifty Falls State Park.  Sugar Maple, Sugar Berry, [...]
1708 E. Dugan Hollow Road, Madison 47250
Phone: 812-340-6082

2nd Street Carriage House

Heart of downtown, historic carriage house (1,000 sq. ft.), queen bed and bath on main floor, kitchen, family room, 2 twin day bed trundle [...]
308 W. 2nd. Street (back), Madison
Phone: (219) 508-9644

2nd Street Inn

Outstanding location, 1850 one story (1,200 sq. ft.), king bed, 2 twin beds, 2 full baths, kitchen, family, dining room, sleeps 4.
308 W 2nd. St., Madison 47250
Phone: (219) 508-9644

The Fashion House on Central Avenue

Luxurious Historic house in downtown, close to virtually everything. Sleeps 10+  Concierge and chef services available upon request for additional charge. 
320 Central Aveune, Madison
Phone: (812) 599-6179

Family Farmhouse

Beautiful recently constructed farmhouse, seven minutes from historic downtown Madison, or a two minute drive to Hanover College. This house was built for gathering, [...]
3895 W State Road 56, Hanover
Phone: (812) 801-1007

Plass Place

This historic home has been updated and is comfortable and homey. Guests have said the house is sparkling clean. Within walking distance of historic [...]
309 Elm Street, Madison
Phone: (502) 210-1193

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