Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Madison, Indiana
$181 avg/night
Minimum Stay 1 Nights
Bed 2

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 6

Max Sleeps

Night 1 nights

Min Stay

Situated just one and a half blocks from the iconic Milton-Madison Bridge spanning the picturesque Ohio River, Glenda's Overlook offers the perfect retreat for you and your loved ones. Our home is located merely a few walking blocks, or short golf cart ride (golf cart available for additional fee), from the historic district, and offers easy access to the city's charming wineries, shops, restaurants, Crystal Beach and vibrant festivals that Madison has to offer. Additionally, we are only a short drive to Clifty Falls State Park.

Our two-story home features two inviting bedrooms upstairs, each offering captivating views of the Ohio River. The master bedroom boasts a plush Queen bed, while the second bedroom features a cozy Full bed. Both bedrooms share access to a full bathroom, ensuring comfort and convenience for all guests.

Downstairs offers a comfortable memory foam queen sleeper sofa for additional sleeping arrangements. A second full bathroom is conveniently located on the ground floor, providing added flexibility and privacy for guests. Our home can comfortably accommodate up to 6 guests.

Step outside onto our expansive deck, that can be used for extra entertaining space with two separate sitting areas where you can bask in the tranquility of the surrounding forest while sipping morning coffee or enjoying a sunset dinner. Inside, a fully equipped kitchen awaits, complete with a versatile Keurig machine catering to both k-cups and ground coffee enthusiasts. Other amenities include a washer/dryer, three Smart TVs, complimentary high-speed Wi-Fi, a hairdryer, and onsite parking.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Smoke Detector Not Reported (host Has Not Indicated Whether There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Double-glazed Windows Local Artist Showcase Locally-owned & Organized Tours & Activities Unit Size: 950 Sq Ft (88 Sq M) Uses Some LED Lighting Water-efficient Showers Only
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Kitchen Island Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Outdoor Furniture Patio
  • BATHROOMS

    2 Bathrooms Hair Dryer Shampoo Shower Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • ENTERTAINMENT

    Games Smart TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Games
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Availability

Review Review

  • Janet

    Submitted Aug 9, 2025

    Stayed Aug 7, 2025

    We enjoyed the space. Had everything we needed. Great proximity to downtown shopping and entertainment.

  • Julie

    Submitted Mar 11, 2025

    Stayed Mar 10, 2025

    Clean, comfortable home with everything needed for our stay.

  • Julie L.

    Submitted Mar 22, 2026

    Stayed Mar 20, 2026

    We were very pleased with the location and cleanliness of the home. Comfy and cozy atmosphere and communication with owner was great! Highly recommend for a nice quiet getaway!

  • Grace A.

    Submitted Mar 11, 2026

    Stayed Mar 8, 2026

    It was great! It had everything we needed!

  • Vickie T.

    Submitted Mar 8, 2026

    Stayed Mar 7, 2026

    Loved the House! Very clean and well decorated. Host was very nice and very easy to communicate with. Definitely recommend!

  • Paul K.

    Submitted Jan 15, 2026

    Stayed Jan 13, 2026

    Bedroom upstairs not excited about that,Traffic sound to loudGetting out of driveway to hardNo ice when we got there

  • ANGIE M.

    Submitted Dec 19, 2025

    Stayed Dec 17, 2025

    Everything was good. We plan to visit Madison again. Thanks

  • David K.

    Submitted Dec 5, 2025

    Stayed Nov 29, 2025

    Everything was great. The VRBOsite made it a little difficult to see code for entry. However the place and host were very nice. I will let my friends know about your Glenda's Overlook.

  • Amy H.

    Submitted Dec 1, 2025

    Stayed Nov 27, 2025

    Had a great stay! Clean and comfortable. Exactly as described!

  • Jacob C.

    Submitted Nov 29, 2025

    Stayed Nov 25, 2025

    Great spot. Love Madison!!!!

  • Lauren H.

    Submitted Nov 14, 2025

    Stayed Nov 7, 2025

    Adorable place, very clean and modern. Loved the kitchen area and the master bed was very comfortable for sleeping!

  • Laurie R.

    Submitted Nov 4, 2025

    Stayed Oct 31, 2025

    We enjoyed our stay. The hosts were very accommodating and the space is cozy, welcoming and beautifully decorated. The upper deck/patio area is really nice. Easy location to go for a walk along the river.

  • Submitted Oct 29, 2025

    Stayed Oct 26, 2025

    We were so excited to have a little getaway and were pleased to stay in such a lovely, updated home. Everything was welcoming as we entered, all was in order and worked nicely. Madison is a beautiful little town!

  • Joan B.

    Submitted Oct 26, 2025

    Stayed Oct 23, 2025

    We loved the space. It was clean, well appointed, and comfortable. The pictures on line represent it well. The only difficulty we had was the loud traffic noise made it hard to sleep. It is on a busy road. The mirror to check for traffic when backing out of driveway was so great! The host had many thoughtful additions…including a welcome bottle of wine! The host responded quickly to any question! Overall, we would give the house a 4.7 because of the traffic noise.

  • Heather E.

    Submitted Oct 25, 2025

    Stayed Sep 21, 2025

    This was perfect and had everything! We each had our own space and the beds were so comfy! All around a great place!!!

  • Songa B.

    Submitted Oct 19, 2025

    Stayed Oct 17, 2025

    Amazing property, clean room, comfy beds and close to main shoppinh

  • Paul P.

    Submitted Oct 18, 2025

    Stayed Oct 5, 2025

    Nice friendly town and eating places

  • Andrea N.

    Submitted Oct 9, 2025

    Stayed Oct 2, 2025

    We loved the house! It was beautiful and just what we needed for our long weekend visiting Madison and Clifty Falls State Park. Chris was very responsive when I reached out prior to our stay and the bottle of wine awaiting us when we arrived was a lovely surprise. The deck on the back of the house was the perfect spot to enjoy that gift. The house is a quick walk to the river front, which we walked everyday/evening. It didn’t greatly impact your stay, but you will hear a great deal of traffic throughout the day and evening as the house is just a few feet off of a busy road. There were also no hangers in any of the closets, so hopefully those can be added. Those small details did not greatly impact us and we still loved the house! We will definitely stay again.

  • Lorraine C.

    Submitted Sep 17, 2025

    Stayed Sep 15, 2025

    Beautiful and very comfortable home.Easy access to town, restaurants, &River. Host was very friendly and helpful.

  • Mary S.

    Submitted Sep 7, 2025

    Stayed Sep 4, 2025

    Beautiful little house close to town. Perfect for our cousins weekend!

  • Glen J.

    Submitted Sep 1, 2025

    Stayed Jun 2, 2025

    Wonderful place in Madison, Indiana! Updated throughout and very cozy. Will be back again!

  • Kelly N.

    Submitted Aug 12, 2025

    Stayed Aug 4, 2025

    Adorable home with all the amenities you need. Close to down town Madison. Perfect for our short stay to visit with family. Would definitely stay again.

  • Karen W.

    Submitted Aug 4, 2025

    Stayed Aug 2, 2025

    We were able to check in early. The house is very cute and we enjoyed using the golf cart to explore around town. We enjoyed hanging out in the evening in the house. It had everything we needed and it was very clean. We would definitely stay there again,

  • Paul W.

    Submitted Jul 27, 2025

    Stayed Jul 25, 2025

    It is a nice place. We were able to walk to the river and main street fairly easy.

  • Sally R.

    Submitted Jul 25, 2025

    Stayed Jul 14, 2025

    Very close to the shops downtown. A very comfortable stay. And Chris is great to work with.

  • Tabitha H.

    Submitted Jul 25, 2025

    Stayed Jul 20, 2025

    Beautiful home, wonderful communication from owner. House was very clean and so comfortable. Very impressed and would definitely stay again.

  • Frank F.

    Submitted Jul 16, 2025

    Stayed Apr 18, 2025

    The two of us had a weekend getaway. On other visits, we stayed closer to Main Street, but this location was perfectly fine. Walking around Madison is easy and enjoyable. This home is new and well done. Would definitely recommend.

  • Robert M.

    Submitted Jul 7, 2025

    Stayed Jun 29, 2025

    Two nights really enjoyed it

  • Joshua H.

    Submitted Jun 4, 2025

    Stayed May 29, 2025

    Very Clean and easy to access.

  • Joseph E.

    Submitted May 21, 2025

    Stayed May 8, 2025

    Easy self check-in. Everything was great

  • Kevin C.

    Submitted Apr 9, 2025

    Stayed Apr 4, 2025

    The home was a nicely refurbished older structure just on the east edge of Madison and very near the bridge to Kentucky. The bathrooms were roomy and the bedrooms comfy.If you do rent this house, I don't see how more than four guests could comfortably stay there. Downstairs main area felt cramped at times with 4 adults.The only serious drawback I felt was the driveway of the property. Frankly, it was rather small and felt more like a launching pad given the extreme angle of the entrance and exit.

  • Amy H.

    Submitted Mar 4, 2025

    Stayed Mar 1, 2025

    Home was very clean, driveway is steep and difficult to see when you are backing out. Bedrooms and bathrooms spacious. Kitchen is on the small side but functional. Over all, a very nice home.

  • Joshua C.

    Submitted Feb 23, 2025

    Stayed Jan 17, 2025

    We stayed in this property on our annual Madison visit. It had everything we needed and was very comfortable and clean. We would stay here again.

  • Melanie C.

    Submitted Feb 20, 2025

    Stayed Feb 15, 2025

    We visit Madison at least twice a year. We decided to try a VRBO instead of staying in a hotel as we normally do.Glenda's Overlook exceeded our expectations. It was clean and well supplied. Our daughter was excited to find a TV in her bedroom. It snowed during our stay and my husband was happy to find a snow shovel out back. The driveway is a bit of an upward incline, so the shovel was great. I enjoyed all the bits of Madison included in the decor. Host was very responsive. Can't wait to visit in warmer weather so we can enjoy the deck and woods.

  • Steve P.

    Submitted Jan 26, 2025

    Stayed Jan 25, 2025

    Had a good time

  • Tobi H.

    Submitted Dec 1, 2024

    Stayed Nov 30, 2024

    Property was comfortable, new and clean. Easily fit our group of 4. Location ok, but quite a walk to Madison stores and restaurants. On a warm night I’m sure golf cart rental would have been fun. We would definitely stay again.

  • Carrie G.

    Submitted Nov 25, 2024

    Stayed Nov 21, 2024

    Beds were comfortable, space was cozy, location ideal to everything. Wouldn’t hesitate to recommend to others and would stay again. Super helpful host!

  • Nicole M.

    Submitted Nov 25, 2024

    Stayed Nov 14, 2024

    We made a quick trip to Madison for my husband’s birthday. The house was beautiful-wish we had been able to stay longer!

  • Theresa B.

    Submitted Nov 15, 2024

    Stayed Nov 13, 2024

    Modern, clean, close to downtown home that perfectly served our Madison stay. Thank you for your hospitality!

  • Marypat C.

    Submitted Nov 11, 2024

    Stayed Nov 5, 2024

    We had such a terrific time! The house is close to restaurants, shopping, bars, historical sites. I would recommend the space.

  • Nikki H.

    Submitted Nov 11, 2024

    Stayed Nov 8, 2024

    It was my first time in Madison and I was so happy to have found a house that was so clean and close to mid-town. The house was exceptionally clean and the beds were extremely comfortable. Will definitely stay here again.

  • Submitted Nov 10, 2024

    Stayed Oct 22, 2024

    Great communication with property owner. Very accommodating. We stayed during an invasion of Lady Bird Beetles. The whole town was overrun by them. We would definitely stay at this location again on our next trip to Madison.

  • Michelle R.

    Submitted Sep 23, 2024

    Stayed Sep 20, 2024

    Great stay- beautiful house

  • Lisa M.

    Submitted Sep 21, 2024

    Stayed Sep 17, 2024

    Such a quaint and beautiful town. My friend and I had a wonderful time! The amenities were wonderful! Beautiful property!!

  • Stacy H.

    Submitted Sep 3, 2024

    Stayed Aug 30, 2024

    I really liked the house , very clean and nice !!

  • Debra H.

    Submitted Aug 27, 2024

    Stayed Aug 23, 2024

    Situated perfectly to all the shops and restaurants. Really well cared for and decorated to fit the location. Clean and outfitted with all the amenities we needed. We had a great long weekend in Madison and thoroughly enjoyed this lovely town! Thank you!

  • Roxann W.

    Submitted Aug 3, 2024

    Stayed Aug 1, 2024

    The decorating of this property was above and beyond

  • Marie D.

    Submitted Jul 29, 2024

    Stayed Jul 16, 2024

    We enjoyed the house for a one night stay to hike Clifty Falls and see Madison IN. Well maintained property and easy check in.

  • Cindi C.

    Submitted Jul 21, 2024

    Stayed Jul 20, 2024

    Glenda’s Overlook is great! Very clean and comfortable, everything was thought of and available. Loved the decorating. Would definitely stay here again!!

Your dates are Available!

Total

Includes taxes and fees
$234+
View details