Title: Glenda’s Overlook..everything you need to make visiting Madison a great getaway! - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&selected=105105513&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Glenda’s Overlook..everything you need to make visiting Madison a great getaway! Vacation home in Madison with kitchen and patio ## Photo gallery for Glenda’s Overlook..everything you need to make visiting Madison a great getaway! ![Smart TV - Glenda’s Overlook..everything you need to make visiting Madison a great getaway! (Madison)](https://images.trvl-media.com/lodging/106000000/105110000/105105600/105105513/bf33beba.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Interior - Glenda’s Overlook..everything you need to make visiting Madison a great getaway! (Madison)](https://images.trvl-media.com/lodging/106000000/105110000/105105600/105105513/aab5f477.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop - Glenda’s Overlook..everything you need to make visiting Madison a great getaway! (Madison)](https://images.trvl-media.com/lodging/106000000/105110000/105105600/105105513/7adbb048.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop - Glenda’s Overlook..everything you need to make visiting Madison a great getaway! (Madison)](https://images.trvl-media.com/lodging/106000000/105110000/105105600/105105513/720ba05a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior - Glenda’s Overlook..everything you need to make visiting Madison a great getaway! (Madison)](https://images.trvl-media.com/lodging/106000000/105110000/105105600/105105513/c7ba1628.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Nestled near the Ohio River, Glenda's Overlook offers a serene retreat. Unwind on the expansive deck with two separate sitting areas, bask in forest tranquility while sipping coffee or enjoying sunset dinner. With a fully equipped kitchen and versatile Keurig machine, you'll feel right at home. ## Reviews 9.8 Exceptional ### Entire home 2 bedrooms2 bathroomsSleeps 6950 sq ft ## Popular amenities - Kitchen - Washer - Dryer - Air conditioning - Outdoor Space - Parking available ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Glenda’s Overlook..everything you need to make visiting Madison a great getaway! 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. ## Property amenities ### Internet - Available in the house: WiFi ### Parking and transportation - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Kitchen island - Microwave - Oven - Refrigerator - Stovetop - Toaster ### Bedrooms - 2 bedrooms - Bedsheets provided ### Bathroom - 2 bathrooms - Hair dryer - Shampoo - Shower - Soap - Toilet paper - Towels provided ### Entertainment - Games - Smart TV ### Outdoor areas - Outdoor furniture - Patio ### Laundry - Laundry facilities - Washing machine ### Comfort - Air conditioning - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Smoking not allowed ### Safety features - 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) ### General - At least 80% lighting from LEDs - Double-glazed windows - Local artist showcase - Locally-owned and organized tours and activities - Unit size: 950 square feet - Water-efficient showers - Water-efficient toilets ## Similar properties ![Smart TV](https://images.trvl-media.com/lodging/114000000/113730000/113727100/113727046/ad5d5be4.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining Madison - Kitchen - Washer - Dryer - Pet friendly 10 Exceptional 23 reviews CA $136 CA $277 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-02&endDate=2026-02-03&selected=113727046&PinnedHotelID=113727046&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior detail](https://images.trvl-media.com/lodging/108000000/107290000/107288500/107288402/ed8aca07.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102 Madison - Kitchen - Washer - Dryer - Air conditioning 10 Exceptional 11 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-06&endDate=2026-02-07&selected=107288402&PinnedHotelID=107288402&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior detail](https://images.trvl-media.com/lodging/108000000/107290000/107288500/107288412/55c781c9.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Madison Inn, Historic woodside view suite 205, Historic woodside view suite 205 Madison - Kitchen - Washer - Dryer - Air conditioning 9.8 Exceptional 7 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-06&endDate=2026-02-07&selected=107288412&PinnedHotelID=107288412&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior detail](https://images.trvl-media.com/lodging/108000000/107290000/107288500/107288406/0223362a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201 Madison - Kitchen - Washer - Dryer - Air conditioning 9.6 Exceptional 15 reviews CA $131 CA $213 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-25&endDate=2026-01-26&selected=107288406&PinnedHotelID=107288406&HadPinnedHotel=true®ionId=-1&adults=2) ![Smart TV](https://images.trvl-media.com/lodging/104000000/103270000/103267800/103267789/d187384e.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Hanover Hideaway! 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You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ## About the area Madison is home to this vacation home. Thomas Family Winery and Lanthier Winery are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Clifty Falls State Park and Ohio River Valley. [Visit our Madison travel guide](https://www.expedia.ca/Madison.dx6059636) [View more Vacation homes in Madison](https://www.expedia.ca/Madison-Private-Vacation-Homes.d6059636-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6¢er=38.735126,-85.366776&zoom=13&channel=expedia-HotelInformation&maptype=roadmap&scale=1&path=color:0xFFFFF|weight:2|fillcolor:0x005AEB7F|enc:simkFje%60hO%3FS%3FS%3FU%40S%40S%3FS%40S%40S%40SBQ%40SBS%40SBSBSBQBSDQBSDQDSBQFSDQDQDQFQFQDQFQFOFQHOFOFQHOFQHMHOHOHOHMJMHOJMHMJMJMJKJMHKLKJMJKLKJIJILMLGLILKJGLILILGNGLGLGLENGLENELELENENELCNCNCLCNCNALCN%3FNANANANAL%3FN%3FN%3FN%3FN%40N%40N%40L%40N%3FNBN%40NBLBNBLBNBNDLDNDLDNDLDLFNDLFLFLFNFJHLHLFLJLHJFLLLHJHLJJJJLJJJJJLJJJLJLHLJLHNJLHLHNHNHNFLHPHNFPFNFNHPFNFPDPFPDPFPDPDPDRDPDRBPDRBPDRBR%40PBRBRBR%40R%40PBR%40R%3FR%40R%40R%3FR%40T%3FR%3FR%3FP%3FRAT%3FRARAR%3FRARCRAPARCRCRCRAPCRERCPERCPEREPEREPEPGPEPGPEPGPGNIPGNGNGPINIPGLINININILKLINKLILKLKLKJKLKJKJKLKJMJKHMHMLKFMHMJMFMHKHOFMFMFMFODMFMDODMDODMDODOBMBOBMBOBO%40OBO%3FM%40O%40O%40O%40O%3FO%3FO%3FM%3FOAOAOAOAO%3FMCOAOCMCOCOCMCOEOEMEMEOEMEOGMEMGMGOGMGMIMIKGMKMIMGMMKIKIMKKKKMMKIKKMKKKMKMIMKMIOKMIMIOIOIOIMGQIOGQGOIOGQGOGQEQGQGQEQEQEQGSCQESEQCSEQCSCQCSCSASCSASCQASASAS%3FSASAS%3FU%3FS%3FQ&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=Z9GKcPAFm5hh38kBzhyty1co9wU=) Madison, IN ### What's nearby - ![The First Congregational Church at the Historic District in Downtown Madison, Connecticut, USA](https://images.trvl-media.com/place/553248621532656300/40dd795a-17b6-4125-bec1-89e88a4d7b04.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Historic District 17 min walk \- 1.5 km - ![Madison, Indiana](https://images.trvl-media.com/place/553248621532656295/7f9c5c64-bf0b-46fc-b21f-ce03f9e0a55c.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Lanier Mansion 2 min drive \- 2.1 km - Schofield House 18 min walk \- 1.5 km - Jeremiah Sullivan House 19 min walk \- 1.6 km - Lanthier Winery 3 min drive \- 2.5 km ### Getting around - Louisville Intl. Airport (SDF) 63 min drive ### Restaurants - Circle K 6 min drive - Dairy Queen 2 min drive - The Red Pepperoni 2 min drive - Moose Lodge 4 min drive - Subway 6 min drive ## Frequently asked questions ### Is Glenda’s Overlook..everything you need to make visiting Madison a great getaway! pet-friendly? ### How much does it cost to stay at Glenda’s Overlook..everything you need to make visiting Madison a great getaway!? ### How much is parking? ### What time is check-in at Glenda’s Overlook..everything you need to make visiting Madison a great getaway!? ### What time is check-out at Glenda’s Overlook..everything you need to make visiting Madison a great getaway!? ### Where is Glenda’s Overlook..everything you need to make visiting Madison a great getaway! located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Glenda’s Overlook..everything you need to make visiting Madison a great getaway! Reviews ## Reviews ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. [More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 47 8 - Good 6 6 - Okay 1 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 9.0 Location ### 10 Property conditions & facilities ## Reviews ### 10/10 Excellent #### Paul W. Jul 27, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great place to stay It is a nice place. We were able to walk to the river and main street fairly easy. ##### Paul W. Stayed 2 nights in Jul 2025 ### 10/10 Excellent #### Tabitha H. Jul 25, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Beautiful home, wonderful communication from owner. House was very clean and so comfortable. Very impressed and would definitely stay again. ##### Tabitha H. Stayed 2 nights in Jul 2025 ### 10/10 Excellent #### Julie Mar 11, 2025 Liked: Cleanliness, amenities, property conditions & facilities, communication Clean, comfortable home with everything needed for our stay. ##### Julie Stayed 1 night in Mar 2025 ### 10/10 Excellent #### Joshua C. Feb 23, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Annual Madison visit 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. ##### Joshua C. Stayed 2 nights in Jan 2025 ### 10/10 Excellent #### Carrie G. Nov 25, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### No complaints, would stay again Beds were comfortable, space was cozy, location ideal to everything. Wouldn’t hesitate to recommend to others and would stay again. Super helpful host! ##### Carrie G. Stayed 3 nights in Nov 2024 ### 10/10 Excellent #### Darin B. Jul 6, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Stay Our stay was wonderful. This was a perfect place for our family to visit Madison. We will definitely be booking this property again. ##### Darin B. Stayed 5 nights in Jun 2024 ### 10/10 Excellent #### Lisa M. Sep 21, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Everything was well appointed!! Very lovely getaway!!! Such a quaint and beautiful town. My friend and I had a wonderful time! The amenities were wonderful! Beautiful property!! ##### Lisa M. Stayed 3 nights in Sep 2024 ### 10/10 Excellent #### Cindi C. Jul 21, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great Place Glenda’s Overlook is great! Very clean and comfortable, everything was thought of and available. Loved the decorating. Would definitely stay here again!! ##### Cindi C. Stayed 1 night in Jul 2024 ### 10/10 Excellent #### Nikki H. Nov 11, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great house 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. ##### Nikki H. Stayed 2 nights in Nov 2024 ### 10/10 Excellent #### Theresa B. Nov 15, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Madison Fun! Modern, clean, close to downtown home that perfectly served our Madison stay. Thank you for your hospitality! ##### Theresa B. Stayed 1 night in Nov 2024 ### 10/10 Excellent #### John R. May 31, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great hideaway We tucked in here for a personal getaway for 2 nights. It was perfect. Clean, fresh, comfortable allowed for a very relaxing stay. ##### John R. Stayed 2 nights in May 2024 ### 10/10 Excellent #### Marie D. Jul 29, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Madison stay We enjoyed the house for a one night stay to hike Clifty Falls and see Madison IN. Well maintained property and easy check in. ##### Marie D. Stayed 1 night in Jul 2024 ### 10/10 Excellent #### Marypat C. Nov 11, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect for 3-4 adults We had such a terrific time! The house is close to restaurants, shopping, bars, historical sites. I would recommend the space. ##### Marypat C. Stayed 3 nights in Nov 2024 ### 10/10 Excellent #### Kelly C. May 27, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Cute little getaway! The house is very cute and accommodating! Beds are soft and shower is nice! We paid a little extra to rent his golf cart and that was fun! Great stay in Madison! ##### Kelly C. Stayed 1 night in May 2024 ### 8/10 Good #### Tobi H. Dec 1, 2024 Liked: Cleanliness, check-in, communication, listing accuracy #### Quick visit 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. ##### Tobi H. Stayed 1 night in Nov 2024 ### 10/10 Excellent #### Debra H. Aug 27, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Loved Madison, IN! 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! ##### Debra H. Stayed 3 nights in Aug 2024 ### 10/10 Excellent #### Karen M. Jul 7, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Relaxing We had a nice time. Chris replied to my questions immediately and he went out of his way to help us rent his golf cart. The place was nice and clean. We would stay again. ##### Karen M. Stayed 2 nights in Jun 2024 ### 10/10 Excellent #### Amy H. Mar 4, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Girl’s Weekend 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. ##### Amy H. Stayed 1 night in Mar 2025 ### 10/10 Excellent #### Verified traveller Nov 10, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Warm and welcoming. 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. ##### Verified traveller Stayed 2 nights in Oct 2024 ### 10/10 Excellent #### Amanda S. Jul 8, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Roostertail Festival 2024 Lovely, newly remodeled home. Close to all the shopping, dining, and entertainment Madison IN has to offer. My stay was memorable to say the least. The host is quick to answer the phone or a text message. Thank you for everything Chris! God Bless! ##### Amanda S. Stayed 2 nights in Jul 2024 ### 10/10 Excellent #### Melanie C. Feb 20, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Clean, comfy, complete 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. ##### Melanie C. Stayed 2 nights in Feb 2025 ### 10/10 Excellent #### Randy P. Jun 22, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Madison, Indianna Get-Away This property worked out very well for my wife and I on our short get-away to Madison. We loved the furnishings, the street-view, the decor and accessories. It's cleanliness was excellent, even in room corners. The kitchen is a little tight around the large bar but still navigable for a short vacation stay. I loved the private off-the-street parking right off the entry door, as well as the private 2nd floor outdoor deck, although we didn't use it due to the high outside temperatures this week. We will most definitely seek out this property if we get to Madison in the future. Randy ##### Randy P. Stayed 3 nights in Jun 2024 ### 10/10 Excellent #### Sally R. Jul 25, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Very close to the shops downtown. A very comfortable stay. And Chris is great to work with. ##### Sally R. Stayed 4 nights in Jul 2025 ### 10/10 Excellent #### Kevin C. Apr 9, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Madison Getaway 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. ##### Kevin C. Stayed 2 nights in Apr 2025 ### 8/10 Good #### Paul P. Oct 18, 2025 Liked: Check-in, communication, location, listing accuracy Nice friendly town and eating places ##### Paul P. 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