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Jacuzzi in Room · Madison

Hillside Inn

4.2 (596 reviews) $116 - $119 per night Hand-verified for 2026
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Why we picked it

"The 3.8 East Main hilltop Hillside Inn — 4.3 location for Ohio River balcony views."

At a glance
01
831 E Main St
Hilltop district
02
4.3 location subrating
Ohio River views
03
Balcony river-view rooms
Book specifically
04
Free breakfast
24-hour front desk
05
Rating
3.8 out of 5 (241 reviews)

About The Hotel

Hillside Inn is a 3.8-rated (241 reviews) hilltop-view hotel at 831 E Main St in Madison’s Hilltop district. Subratings 4.0 cleanliness, 4.3 location, 3.9 rooms, 4.1 service, 4.2 sleep quality and 3.8 value. Amenities include free parking, WiFi, free breakfast, meeting rooms, non-smoking hotel and 24-hour front desk. Recent 5-star from a 15-time repeat guest praised beautiful balcony views, impeccable rooms, friendly staff and good breakfast. A 4-star called it a friendly hilltop hotel with great views but noted it’s kinda tired. A 3-star flagged 2-star quality despite amazing staff and the harsh cleaning smell in the lobby. A 2-star warned first-floor rooms have poor river views — book a balcony room specifically. About 10-15 minutes walking distance to downtown Madison National Historic Landmark district. Pool-and-hilltop hotel rather than an in-room-jacuzzi property.

What Guests Are Saying

“Enjoyed the view and location. Panoramic balcony view was amazing. Stayed in the suite. The room was clean and nice. Decor could use a bit of updating. WiFi was super fast and we had no problems getting logged in. Staff was outstanding. Staff was friendly and helpful during our stay. The breakfast bar was your typical faire. The coffee was hot and the food ready on time. If you stay here, please be aware that you are driving to the top of a pretty steep hill, so be ready for that. It was a little scary pulling in from the main road. If you’re not careful you could have an accident with the oncoming traffic when you pull out onto the road from the drive. Everything you need is within walking distance. There was one little thing. I’m still not sure if I believe it or not. We had an unexplainable encounter twice on our first night there. The first time it was about 1030 PM and the second at about 230 AM. We were woken up out of a sound sleep by the sound of a child giggling in different areas of the room. The sound was IN OUR ROOM. We checked our cell phones and scouted around and found nothing that could have made that noise. I heard the noise again at about 630 the morning that we left. I was playing on my laptop and the noise was right in front of me. Of course, my husband discounted it as something goofy going on with the laptop, but I’m not so sure. We told the staff about it and she said that there were no kids on site during our stay. So, believe what you want. I think the hotel is a little bit haunted. The desk clerk admitted that we’re not the first to experience strange happenings during our stay. Ghosts aside, I really liked the hotel. I’d probably stay again, only in a different room though.” — FarAway203659, 5 stars

“Although the hotel is older, lots of history here. Well maintained, pleasant, helpful staff. Here with friends and my husband. My friends needed a break from some serious health issues, so we decided on a mini stay near home. Their room heat wasn’t working properly, and it got fixed right away. My friend has trouble sleeping at night, and they let us move a recliner chair from our room to hers. They gave us a good tip for dinner- Harry’s Stone Grill ( go hungry, you’ll need a box too) and it snowed overnight the day before we were leaving, They had the parking lot and the drive down to the main road plowed and treated. Cute town for antiques, wine tasting, shopping, history.” — kytraveler413, 5 stars

“It’s a 1960s Inn, but it is well maintained and clean. The beds are very comfortable. The view from the balcony is GREAT, and they even have a ceiling fan on the balcony. We enjoyed wine on the balcony every evening. They have in room coffee with real coffee mugs (not paper cups), and real drinking glasses too (not plastic). Breakfast included everything you could want (eggs, bacon, sausage, potatoes, waffles, muffins, bagels, yogurt, fruit, cereal, etc, etc). The only down side was the street noise, but I’m guessing that would be an issue with most of the hotels in the area. I would stay here again.” — ssjj123, 5 stars

Pros & Cons

Pros:

  • 4.3 location subrating — Ohio River views
  • Balcony rooms with river views (book specifically)
  • 15-time repeat guest recommends
  • Free breakfast
  • Downtown Madison historic district access

Cons:

  • Older property described as kinda tired
  • First-floor rooms have poor river views
  • Harsh cleaning smell in lobby flagged

The Location

831 E Main St, Madison, IN 47250 — Hilltop district with Ohio River views, walkable to Madison’s National Historic Landmark district. You can find more details or book your stay on TripAdvisor.

What's at the hotel
newspaper Newspaper
wifi Free WiFi
wifi Internet
local_parking Free Parking
free_breakfast Breakfast
meeting_room Meeting Rooms
smoke_free Non-Smoking
ac_unit A/C
kitchen Fridge
smoke_free Non-Smoking
tv TV
hotel Breakfast Buffet
Location & neighborhood

Madison,
Madison.

831 E Main St, Madison, IN 47250-3652
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Guest reviews

What guests are saying about Hillside Inn.

4.2 out of 5· 596 reviews
★★★★★
5/5
a month ago
"Had a pleasant stay! The room was clean, the front desk staff were attentive and welcoming, and the balcony views were lovely. Great location as well, it’s less than a 5 minute drive down the road to several cute restaurants and shops. Will definitely stay here again the next time I’m in Madison."

— Sara Proctor

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★★★★★
5/5
5 months ago
"This is such a cool place!! We loved it. The old history the spectacular view. The town of Madison is beautiful. We were down there riding our motorcycles and tge only thing I can say is the driveway up to it is scary on a bike!! Definitely going back in December and next year getting room 304!! The staff us knowledgeable and so friendly & helpful. The balcony is to die for. Just sit and chill and see the whole town, the bridge that goes right to Kentucky. It's a must to stay there¡"

— Laura Olson

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★★★★
4/5
5 months ago
"The staff was great and rooms were nice, continental breakfast was average and good. I'd like to see the front door entrance cleaned up and Ditch the ashtray by the door and smokers bench needs to go. It's unpleasant walking up to the entrance and smelling cigarettes. Ice machine needs repaired. Vent above the shower is open and kinda creepy . Great location with a short walk to downtown and beautiful balcony view."

— Tony Vaughn

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