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

Madison vacation home with kitchen

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

Fridge, microwave, oven, stovetop
Outdoor dining
Fridge, microwave, oven, stovetop
Smart TV
Exterior

Reviews

9.8 out of 10
Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 6950 sq ft

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Outdoor Space
  • Kitchen
  • Air conditioning

Explore the area

View in a map
Madison, IN
  • Place, Historic District
    ‪17 min walk‬
  • Place, Schofield House
    ‪18 min walk‬
  • Place, Lanier Mansion
    ‪2 min drive‬

Room options

About the neighborhood

Madison

In Madison .Within a 5-minute walk of the vacation home, you'll find Ohio River Valley and Ohio River. Thomas Family Winery and Historic District are also within 2 miles (3 km).
View more Vacation Homes in MadisonOpens in a new window

What's nearby

  • Historic District - 17 min walk - 1.0 mile
  • Francis Costigan House - 2 min drive - 1.3 miles
  • Lanier Mansion - 2 min drive - 1.3 miles
  • Lanthier Winery - 3 min drive - 1.6 miles
  • Clifty Falls State Park - 4 min drive - 3.1 miles

Getting around

  • Louisville Intl. Airport (SDF) - 63 min drive

Restaurants

  • ‪Dairy Queen - ‬2 min drive
  • ‪The Red Pepperoni - ‬2 min drive
  • ‪Moose Lodge - ‬4 min drive
  • ‪Vintage Lanes Wine Bar - ‬14 min walk
  • ‪Madison Lighthouse Restaurant - ‬2 min drive

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.

Similar properties

Exterior
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
5.0 out of 5, Exceptional, 12 reviews
$146 nightly
The price is $168
Nov 17 - Nov 18
Total with taxes and fees
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

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

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

Pets

  • No pets 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
Onsite 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. Long-term renters welcome.

Frequently asked questions

How close is Glenda’s Overlook..everything you need to make visiting Madison a great getaway! to the airport?

This vacation home is 61.1 mi (63-min drive) away from the Louisville Intl. Airport (SDF) airport, the closest popular airport to the property.

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

As of Nov 14, 2025, 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 Nov 17, 2025 start from $105.0, excluding 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.

Does Glenda’s Overlook..everything you need to make visiting Madison a great getaway! have an airport shuttle?

Airport shuttle services are not available at this vacation home.

Does Glenda’s Overlook..everything you need to make visiting Madison a great getaway! offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Glenda’s Overlook..everything you need to make visiting Madison a great getaway!?

No, there is no casino at this vacation home.

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.

Is there free parking at Glenda’s Overlook..everything you need to make visiting Madison a great getaway!?

Free parking is not available at this vacation home.

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

This vacation home does not have a pool.

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

There are no spa services available at this vacation home.

How close is Glenda’s Overlook..everything you need to make visiting Madison a great getaway! to downtown Madison?

This vacation home is 0.8 mi away from Madison.

Reviews

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

9.8

Exceptional

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Eco-friendliness
Rating 10 - Excellent. 42 out of 47 reviews
Rating 8 - Good. 4 out of 47 reviews
Rating 6 - Okay. 1 out of 47 reviews
Rating 4 - Poor. 0 out of 47 reviews
Rating 2 - Terrible. 0 out of 47 reviews

Reviews

10/10 Excellent

Verified traveler

Liked: Cleanliness
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!
Stayed 2 nights in Oct 2025

10/10 Excellent

Joan B.

Liked: Cleanliness
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.
Stayed 3 nights in Oct 2025

10/10 Excellent

Heather E.

Liked: Cleanliness
This was perfect and had everything! We each had our own space and the beds were so comfy! All around a great place!!!
Stayed 1 night in Sep 2025

10/10 Excellent

Songa B.

Liked: Cleanliness
Amazing property, clean room, comfy beds and close to main shoppinh
Stayed 2 nights in Oct 2025

8/10 Good

Paul P.

Nice friendly town and eating places
Stayed 10 nights in Oct 2025

10/10 Excellent

Andrea N.

Liked: Cleanliness
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.
Stayed 3 nights in Oct 2025

10/10 Excellent

Lorraine C., North Webster

Liked: Cleanliness
Beautiful and very comfortable home.Easy access to town, restaurants, &River. Host was very friendly and helpful.
Stayed 2 nights in Sep 2025

10/10 Excellent

Mary S.

Liked: Cleanliness
Beautiful little house close to town. Perfect for our cousins weekend!
Stayed 3 nights in Sep 2025

10/10 Excellent

Glen J.

Liked: Cleanliness
Wonderful place in Madison, Indiana! Updated throughout and very cozy. Will be back again!
Stayed 3 nights in Jun 2025

10/10 Excellent

Kelly N.

Liked: Cleanliness
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.
Stayed 3 nights in Aug 2025

10/10 Excellent

Janet

Liked: Cleanliness, property conditions & facilities
We enjoyed the space. Had everything we needed. Great proximity to downtown shopping and entertainment.
Stayed 2 nights in Aug 2025

10/10 Excellent

Karen W.

Liked: Cleanliness

Mother/ daughters getaway

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,
Stayed 1 night in Aug 2025

10/10 Excellent

Paul W.

Liked: Cleanliness

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

Sally R.

Liked: Cleanliness
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

Tabitha H.

Liked: Cleanliness
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

Frank F.

Liked: Cleanliness
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.
Stayed 2 nights in Apr 2025

10/10 Excellent

Robert M.

Liked: Cleanliness

Quiet neighborhood

Two nights really enjoyed it
Stayed 2 nights in Jun 2025

10/10 Excellent

Joshua H.

Liked: Cleanliness

Well Renovated

Very Clean and easy to access.
Stayed 2 nights in May 2025

10/10 Excellent

Joseph E.

Liked: Cleanliness

Short, easy stay

Easy self check-in. Everything was great
Stayed 2 nights in May 2025

6/10 Okay

Wesley B.

Stayed 2 nights in Mar 2025

10/10 Excellent

Kevin C.

Liked: Cleanliness

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

10/10 Excellent

Julie

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

10/10 Excellent

Amy H.

Liked: Cleanliness

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

Joshua C.

Liked: Cleanliness

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

Melanie C.

Liked: Cleanliness

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