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

Holiday 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)
Interior - Glenda’s Overlook..everything you need to make visiting Madison a great getaway! (Madison)
Exterior - Glenda’s Overlook..everything you need to make visiting Madison a great getaway! (Madison)
Fridge, microwave, oven, stovetop - Glenda’s Overlook..everything you need to make visiting Madison a great getaway! (Madison)
Fridge, microwave, oven, stovetop - Glenda’s Overlook..everything you need to make visiting Madison a great getaway! (Madison)
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 out of 10
Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 688 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space
  • Parking available
The current price is NZ$378
includes taxes & fees
27 Jan - 28 Jan

Add dates for prices

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 transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • 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

  • Smoke-free property

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 organised tours and activities
  • Unit size: 950 square feet
  • Water-efficient showers
  • Water-efficient toilets

Similar properties

Smart TV
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
10.0 out of 10, Exceptional, 23 reviews
The price is NZ$343
includes taxes & fees
2 Feb - 3 Feb
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age - 24

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome
Note from host: parents will need to monitor closely

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Long-term renters welcome
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. 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 holiday 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
View more Holiday homes in Madison
Map
Madison, IN

What's nearby

  • The First Congregational Church at the Historic District in Downtown Madison, Connecticut, USA
    Historic District
    17 min walk - 1.5 km
  • Madison, Indiana
    Lanier Mansion
    2 min drive - 2.1 km
  • Dr. William Hutching's Office & Hosptal
    17 min walk - 1.5 km
  • Schofield House
    18 min walk - 1.5 km
  • Jeremiah Sullivan House
    19 min walk - 1.6 km

Getting around

  • Louisville International 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?

No, pets are not allowed at this property.

How much does it cost to stay at Glenda’s Overlook..everything you need to make visiting Madison a great getaway!?

As of 22 Jan 2026, prices found for a 1-night stay for 2 adults at Glenda’s Overlook..everything you need to make visiting Madison a great getaway! on 27 Jan 2026 start from NZ$378.28, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Glenda’s Overlook..everything you need to make visiting Madison a great getaway!?

On-site parking is available at the property.

What time is check-in at Glenda’s Overlook..everything you need to make visiting Madison a great getaway!?

Check-in begins at 3:00 PM.

What time is check-out at Glenda’s Overlook..everything you need to make visiting Madison a great getaway!?

Checkout is at 11:00 AM.

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

Situated in Madison, this holiday home is within a 5-minute walk of Ohio River Valley and Ohio River. Thomas Family Winery and Historic District are also within 1 mile (2 km).

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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 informationOpens in a new window
Rating 10 - Excellent. 47 out of 54 reviews
Rating 8 - Good. 6 out of 54 reviews
Rating 6 - Okay. 1 out of 54 reviews
Rating 4 - Poor. 0 out of 54 reviews
Rating 2 - Terrible. 0 out of 54 reviews

10

Cleanliness

9.0

Location

10

Property conditions & facilities

Reviews

10/10 Excellent

Paul W.

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.
Stayed 2 nights in Jul 2025

10/10 Excellent

Tabitha H.

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.
Stayed 2 nights in Jul 2025

10/10 Excellent

Julie

Liked: Cleanliness, amenities, property conditions & facilities, communication
Clean, comfortable home with everything needed for our stay.
Stayed 1 night in Mar 2025

10/10 Excellent

Joshua C.

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.
Stayed 2 nights in Jan 2025

10/10 Excellent

Carrie G.

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!
Stayed 3 nights in Nov 2024

10/10 Excellent

Darin B.

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.
Stayed 5 nights in Jun 2024

10/10 Excellent

Lisa M.

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!!
Stayed 3 nights in Sep 2024

10/10 Excellent

Cindi C.

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!!
Stayed 1 night in Jul 2024

10/10 Excellent

Nikki H.

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.
Stayed 2 nights in Nov 2024

10/10 Excellent

Theresa B.

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!
Stayed 1 night in Nov 2024

10/10 Excellent

John R.

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.
Stayed 2 nights in May 2024

10/10 Excellent

Marie D.

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.
Stayed 1 night in Jul 2024

10/10 Excellent

Marypat C.

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.
Stayed 3 nights in Nov 2024

10/10 Excellent

Kelly C.

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!
Stayed 1 night in May 2024

10/10 Excellent

Debra H.

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!
Stayed 3 nights in Aug 2024

8/10 Good

Tobi H.

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.
Stayed 1 night in Nov 2024

10/10 Excellent

Karen M.

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.
Stayed 2 nights in Jun 2024

10/10 Excellent

Amy H.

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.
Stayed 1 night in Mar 2025

10/10 Excellent

Verified traveller

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.
Stayed 2 nights in Oct 2024

10/10 Excellent

Amanda S.

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!
Stayed 2 nights in Jul 2024

10/10 Excellent

Melanie C.

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.
Stayed 2 nights in Feb 2025

10/10 Excellent

Randy P.

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
Stayed 3 nights in Jun 2024

10/10 Excellent

Sally R.

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.
Stayed 4 nights in Jul 2025

10/10 Excellent

Kevin C.

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.
Stayed 2 nights in Apr 2025

8/10 Good

Paul P.

Liked: Check-in, communication, location, listing accuracy
Nice friendly town and eating places
Stayed 10 nights in Oct 2025