See all properties

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

Top rated by guests

Exterior

Interior

Private kitchen

Living area

Private kitchen

10.0Outstanding

(54 Ratings)

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

Lorraine C.

Don't miss out! Price and availability may change

10.0 / 10.0

Outstanding(54 Ratings)

House in Indiana

6 guests · 2 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Well priced for this locationPriced under area average

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

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.

Map of Indiana

city location on map

Nearby attractions

Eagle Creek Park

Fort Harrison State Park

Things to know

Additional fees to expect

Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Vrbo properties are professionally cleaned after each stay.

Booking feeNo booking fees, easy credit card payments.

Service feeThis helps Vrbo provide a safer and more secure booking experience.

TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.

Customer support

Customer support is handled by our partner Vrbo

$$$$

Top rated by guests

10.0Outstanding

(54 Ratings)

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

Lorraine C.

Don't miss out! Price and availability may change

$$$$

10.0 / 10.0

Outstanding(54 Ratings)

House in Indiana

6 guests · 2 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Well priced for this locationPriced under area average

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

Map of Indiana

city location on map

Nearby attractions

Eagle Creek Park

Fort Harrison State Park

About this house rental

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.

Things to know

Additional fees to expect

Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Vrbo properties are professionally cleaned after each stay.

Booking feeNo booking fees, easy credit card payments.

Service feeThis helps Vrbo provide a safer and more secure booking experience.

TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.

Customer support

Customer support is handled by our partner Vrbo

Ratings and reviews

10.0 / 10.0

Outstanding(54 Ratings)

10.0 / 10.0

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

10.0 / 10.0

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

10.0 / 10.0

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

10.0 / 10.0

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.

10.0 / 10.0

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

10.0 / 10.0

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,

10.0 / 10.0

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

10.0 / 10.0

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

10.0 / 10.0

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

10.0 / 10.0

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.

10.0 / 10.0

Two nights really enjoyed it

10.0 / 10.0

Very Clean and easy to access.

10.0 / 10.0

Easy self check-in. Everything was great

10.0 / 10.0

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.

10.0 / 10.0

Clean, comfortable home with everything needed for our stay.

10.0 / 10.0

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.

10.0 / 10.0

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.

10.0 / 10.0

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.

8.0 / 10.0

Had a good time

8.0 / 10.0

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.

10.0 / 10.0

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

10.0 / 10.0

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

10.0 / 10.0

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

10.0 / 10.0

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.

10.0 / 10.0

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

10.0 / 10.0

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.

10.0 / 10.0

Great stay- beautiful house

10.0 / 10.0

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

10.0 / 10.0

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

10.0 / 10.0

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!

10.0 / 10.0

The decorating of this property was above and beyond

10.0 / 10.0

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

10.0 / 10.0

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

10.0 / 10.0

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!

10.0 / 10.0

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.

10.0 / 10.0

Our stay was wonderful. This was a perfect place for our family to visit Madison. We will definitely be booking this property again.

10.0 / 10.0

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

10.0 / 10.0

We tucked in here for a personal getaway for 2 nights. It was perfect. Clean, fresh, comfortable allowed for a very relaxing stay.

10.0 / 10.0

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!

FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Glenda’s Overlook..everything you need to make visiting Madison a great getaway!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

Explore similar stays in Indiana

Explore all rentals in Indiana

10.0 / 10.0

Outstanding(1 Rating)

7Mi Louisville Pet-Friendly Home

6 guests · 3 bedrooms · 1 bath

The best choice in Indiana for House, for $133 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

10.0 / 10.0

Outstanding(1 Rating)

7Mi Louisville Pet-Friendly Home

6 guests · 3 bedrooms · 1 bath

Enjoy the best of Indiana in our House, 7Mi Louisville Pet-Friendly Home. A stunning property with amenities including Pets allowed and Non-smoking, and more.

10.0 / 10.0

Outstanding(1 Rating)

Kentucky Bourbon Loft about Downtown Louisville

11 guests · 2 bedrooms · 3 baths

Free WiFi/internet

Apartment in Indiana, for $143 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

You can save with One Key

9.7 / 10.0

Outstanding(70 Ratings)

Book a date on State Street

6 guests · 2 bedrooms · 1 bath

The best choice in Indiana for House, for $165 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

6.0 / 10.0

Average(2 Ratings)

Cozy open floor plan

8 guests · 3 bedrooms · 4 baths

Looking for a memorable stay in Indiana? Our House might just be what you're looking for. Enjoy amenities including Family friendly, and more during your stay.

8.8 / 10.0

Excellent(3 Ratings)

Bright New Albany Home 12 Mi to Churchill Downs!

6 guests · 3 bedrooms · 2 baths

This attractive House in Indiana, $156 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

10.0 / 10.0

Outstanding(8 Ratings)

Blissful Bungalow on National Historic St in New Albany, 1 mile from Ohio River

6 guests · 2 bedrooms · 1 bath

This House for $137 in Indiana, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

10.0 / 10.0

Outstanding(12 Ratings)

Uptown Class

15 guests · 3 bedrooms · 2 baths

Are you ready to indulge in a relaxing getaway? Our House in Indiana has everything you need for a rejuvenating stay. Treat yourself to Uptown Class's exceptional amenities, such as No pets allowed, Family friendly and Non-smoking.

Cozy 4BR 2BA Home in Parkland | 4Miles to Downtown

8 guests · 4 bedrooms · 2 baths

When traveling to Indiana, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $138 per night.

Spacious Craftsman Getaway – Minutes from Louisville & the Bourbon Trail!

13 guests · 4 bedrooms · 2 baths

Experience vacation in Indiana with our House, Spacious Craftsman Getaway – Minutes from Louisville & the Bourbon Trail!. Enjoy amenities such as Pets allowed and Family friendly, and more.

Cozy 4BR 2BA Home in Parkland | 4Miles to Downtown

8 guests · 4 bedrooms · 2 baths

Looking for a Apartment in Indiana, this Apartment for $138 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

Charming 2-bedroom house in fantastic Louisville.

6 guests · 2 bedrooms · 1 bath

This inviting House in Indiana can fit your needs for many types of vacations, at $124 per night.

4.0 / 10.0

(1 Rating)

Family Friendly, Free Parking, WiFi, Spacious, Historically Modern Living

6 guests · 2 bedrooms · 1 bath

Looking for the perfect place to call home during your trip to Indiana? This House offers a comfort and style with top-notch amenities, including No pets allowed, Family friendly and Non-smoking, and more.

9.0 / 10.0

Outstanding(2 Ratings)

Modern 2 Bedroom Condo in Louisville

6 guests · 2 bedrooms · 1 bath

Looking for a Apartment in Indiana, this Apartment for $142 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

9.8 / 10.0

Outstanding(88 Ratings)

★ Victorian Louisville ★ 1000 sqft Glassworks Loft

8 guests · 1 bedroom · 1 bath

Discover the beauty of Indiana with a stay at ★ Victorian Louisville ★ 1000 sqft Glassworks Loft, a top rated Apartment with amenities such as Pets allowed, Family friendly and Non-smoking, and more.

You can save with One Key

9.6 / 10.0

Outstanding(5 Ratings)

The Kernel (Downtown Louisville w/ View)

8 guests · 1 bedroom · 1 bath

Nestled in Indiana, this Apartment is perfect for your next vacation. Enjoy The Kernel (Downtown Louisville w/ View)'s top-rated amenities, including No pets allowed, Family friendly and Non-smoking, and more.

5.7 / 10.0

(4 Ratings)

Luxury Home Close to Nulu Downtown 4th w Kings

8 guests · 3 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Garden

Are you ready to indulge in a relaxing getaway? Our House in Indiana has everything you need for a rejuvenating stay. Treat yourself to Luxury Home Close to Nulu Downtown 4th w Kings's exceptional amenities, such as Free Parking, Garden and WiFi/Internet.

9.8 / 10.0

Outstanding(8 Ratings)

Spacious 3 BR Ranch House W/Patio Yard in a quiet Suburb

6 guests · 3 bedrooms · 2 baths

Looking to create some memories in Indiana? Look no further than our House, Spacious 3 BR Ranch House W/Patio Yard in a quiet Suburb . Enjoy top-rated amenities including Family friendly and Non-smoking, and more.

9.6 / 10.0

Outstanding(5 Ratings)

The Kernel (Downtown Louisville w/ View)

8 guests · 1 bedroom · 1 bath

Looking for a memorable stay in Indiana? Our Apartment might just be what you're looking for. Enjoy amenities including No pets allowed, Family friendly and Non-smoking, and more during your stay.

9.8 / 10.0

Outstanding(88 Ratings)

★ Victorian Louisville ★ 1000 sqft Glassworks Loft

8 guests · 1 bedroom · 1 bath

Looking for a Apartment in Indiana, this Apartment for $178 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

9.8 / 10.0

Outstanding(11 Ratings)

The Cardinal (Downtown Louisville)

6 guests · 1 bedroom · 1 bath

Apartment in Indiana, for $164 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

9.0 / 10.0

Outstanding(8 Ratings)

Edgewood: Work Friendly & Near Downtown

in Jeffersonville

8 guests · 3 bedrooms · 2 baths

This inviting House in Indiana can fit your needs for many types of vacations, at $154 per night.

9.0 / 10.0

Outstanding(4 Ratings)

Luxury 2 bedroom 2 full bathroom apartment across from the waterfront!

6 guests · 2 bedrooms · 2 baths

Are you ready to indulge in a relaxing getaway? Our Apartment in Indiana has everything you need for a rejuvenating stay. Treat yourself to Luxury 2 bedroom 2 full bathroom apartment across from the waterfront!'s exceptional amenities, such as No pets allowed and Non-smoking.

10.0 / 10.0

Outstanding(6 Ratings)

3807 Hamburg pike,New Home 2025, perfect for a family ,With a Jacuzzi hot tub,

in Jeffersonville

6 guests · 3 bedrooms · 2 baths

Looking for the perfect place to call home during your trip to Indiana? This House offers a comfort and style with top-notch amenities, including Pets allowed, Family friendly and Non-smoking, and more.

10.0 / 10.0

Outstanding(2 Ratings)

American Pharoah Twin Spires Suite

in Jeffersonville

6 guests · 1 bedroom · 1 bath

Looking for a Apartment in Indiana, this Apartment for $123 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

7.0 / 10.0

Good(8 Ratings)

Veronica's Place: Work Friendly & Near Downtown

in Jeffersonville

6 guests · 3 bedrooms · 2 baths

This House for $154 in Indiana, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

You can save with One Key

10.0 / 10.0

Outstanding(2 Ratings)

American Pharoah Twin Spires Suite

in Jeffersonville

6 guests · 1 bedroom · 1 bath

The best choice in Indiana for Apartment, for $123 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

10.0 / 10.0

Outstanding(2 Ratings)

Secretariat Twin Spires Suite!

in Jeffersonville

6 guests · 1 bedroom · 1 bath

Soak up the beauty of Indiana in our Apartment, Secretariat Twin Spires Suite!. With a range of amenities such as Pets allowed, Family friendly and Non-smoking, you'll feel right at home.

10.0 / 10.0

Outstanding(10 Ratings)

Derby Favorite Near Churchill Downs | Sleeps 8!

8 guests · 3 bedrooms · 2 baths

Experience the best of Indiana with this House available for $162. This property is equipped with amenities including No pets allowed, Family friendly and Non-smoking, and more.

You can save with One Key

2.0 / 10.0

(1 Rating)

Stylish 3BR Near Churchill Downs for Derby Week!

8 guests · 3 bedrooms · 1 bath

Business stays, family stays, couples stay, getaway vacation, and rental in Indiana at Stylish 3BR Near Churchill Downs for Derby Week! for $163 for your next trip.