Vacation rentals in Madison

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Popular amenities for Madison vacation rentals

Vacation rentals with pools in Madison

Guest favorite
Apartment in Aurora
4.89 out of 5 average rating, 36 reviews

Family-friendly 2BR Hot Tub & Pool

andrewRating, 5 stars1 week ago
awesome place, close to town but secluded, pool and hot tub did not disappoint, cool layout plenty of seating, good ac, loved the projector and surround sound we watched 2 family movies and had a great time, kids loved the love sacs. As fellow hosts nice work
Superhost
Guesthouse in Pendleton
4.87 out of 5 average rating, 68 reviews

The Waterfall Place, Suite and Walkout!

KatRating, 5 stars6 days ago
We had a great stay! We were there for a bachelorette trip and it was the perfect spot. It was secluded in this beautiful spot in the woods, the rooms were big and spacious. The waterfall was an amazing touch and the brides only request was a pool and hot tub; and Alicia had both! Very much recommend this place for a getaway with your friends.
Guest favorite
Home in Borden
4.87 out of 5 average rating, 39 reviews

Private Country Getaway 20min to Louisville w/Pool

CoreyRating, 5 stars8 months ago
This is a great place to stay, peaceful and quiet! Pool, hot tub, and bar came in handy when relaxing The margarita maker was clutch lol Dustin is always responsive when needed!
Guest favorite
Home in Aurora
4.91 out of 5 average rating, 35 reviews

"French Riviera" Long Term Discounts

ІванRating, 5 stars3 months ago
Very nice place, I like it. My recommendation, thank you
Guest favorite
Home in Aurora
4.93 out of 5 average rating, 71 reviews

Unique Luxury Family Retreat

DonnaRating, 5 stars1 week ago
This was our first time in arranging accomodations through an Airbnb so I was a little nervous. However my anxiety was releived upon seeing the actual accomodations. The directions given on line were accurrate and the cleanliness was very evident. We had one minor issue on which we needed to contact Patrick and his response was very prompt and helpful. We had not seen some of our family for several years, so having this home available for our reunion was perfect. Thank you so much for opening your home to us.
Guest favorite
Home in Hanover
4.83 out of 5 average rating, 12 reviews

The Hanover O-Asis

PatsiRating, 5 stars2 months ago
This home looked new, very clean and open. The extras, games, snacks, coffee were great. we could walk to Hanover College which was why we were there. Road noise mentioned in the listing was so minimal, we really never noticed. This home is beautiful and very comfortable. Will absolutely go back when we visit grandaughter in college!
Home in Goshen
4.73 out of 5 average rating, 11 reviews

The Boathouse: A Peaceful Paradise

KyleRating, 5 stars8 months ago
This place was amazing. Both Wes and Rachel were extremely accommodating and had everything we needed ready. The place was clean and stocked with everything to make our stay perfect. The boat ride down the river made for a memorable highlight. We will be back!
Top guest favorite
Home in Goshen
5 out of 5 average rating, 68 reviews

Relaxing River Retreat with Private Pool

MaryRating, 5 stars7 months ago
Absolutely perfect! I would say this AirBnb is one of the best that we’ve stayed at. Amazing views of the river. Kristen was very responsive and had everything we needed at the house. The kitchen was stocked with everything you need to cook meals. Beds were comfortable and there were plenty of towels and hot water! I definitely recommend Kristen’s house! I know I didn’t want to leave!

Other great vacation rentals in Madison

Top guest favorite
Home in Madison
4.99 out of 5 average rating, 81 reviews

Cabin in the Holler

JenniferRating, 5 stars1 week ago
The cabin is amazing..Pauline was a amazing host and so welcoming. The property was stunning and was just what was neesed to relax and regroup
Top guest favorite
Home in Madison
5 out of 5 average rating, 81 reviews

Walnut Street Saloon BNB

SharonRating, 5 stars6 days ago
Highly recommend this rental. The location is great! We gathered for a family get together and it was spacious and comfortable. The history of the building and neighborhood was charming too. Our host made us feel very welcome.
Top guest favorite
Guesthouse in Madison
4.95 out of 5 average rating, 86 reviews

Studio apartment above Garage in downtown Madison

SaraRating, 5 stars1 week ago
We loved our stay at Ray’s! The apartment was very nice and clean. The outdoor area is so peaceful with beautiful plants, plenty of seating and a koi pond. Ray was a kind and gracious host. We will definitely stay here again!
Guest favorite
Guest suite in Hanover
5 out of 5 average rating, 66 reviews

OFF THE CLOCK River House

KylieRating, 5 stars7 months ago
Amazing hosts! Great place with a beautiful view! Incredibly friendly and helpful and we had the best time! Thank you!!
Top guest favorite
Home in Madison
5 out of 5 average rating, 22 reviews

Annies Fabulous Federal house

LaurenRating, 5 stars5 days ago
Beautiful place! My spouse and I stayed here with our 2 pups for 4 nights and it felt like a home away from home. Very cozy, and it was so clean when we showed up. The king bed was SO comfy, I wanted to take it with us when we left. I slept incredible. She left great instructions, and checking in was easy. When we visit back, we only hope this place will be available to book again!!
Guest favorite
Cabin in Madison
4.94 out of 5 average rating, 63 reviews

Historic 1830s Log Cabin in Madison, IN

DavidRating, 5 stars1 month ago
Wow! An amazing cabin in a beautiful setting. Rustic luxury. We can't wait to book a return visit. The cabin was beautifully decorated with a high attention to detail. The hosts were accommodating, and communicated clearly.
Top guest favorite
Home in Madison
5 out of 5 average rating, 15 reviews

Luxury Historic Home Ping Pong, Decks, Walkable

BethanyRating, 5 stars2 weeks ago
Conveniently located in Madison and exceptional home , also Misty was a wonderful host!
Top guest favorite
Home in Madison
4.95 out of 5 average rating, 94 reviews

Watchmaker Place in Historic Madison District

EdieRating, 5 stars2 weeks ago
Beautiful updated home in downtown Madison! Walkable to Main Street and river. Comfortable stay for two couples. One bathroom is on the first floor while both bedrooms are on the second floor. There are no window coverings on the first floor. Would definitely stay there again.

Quick stats about vacation rentals in Madison

  • Total rentals

    120 properties

  • Total number of reviews

    7.6K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    110 properties include access to wifi

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Madison?

    Yes! Work meets play with ease at over 60 vacation rentals in Madison featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Madison?

    Four-legged friends are welcome in Madison. Choose from more than 30 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in boutique hotel rentals in Madison?

    Experience the best of Madison with our boutique hotel rentals, starting at about $160 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Madison have self check-in?

    Absolutely! We offer over 20 house rentals with self check-in in Madison. Enjoy a tailored experience with all the comforts you desire.

  • Do boutique hotel rentals in Madison have wifi?

    Absolutely! We offer over 10 boutique hotel rentals with wifi in Madison. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Madison?

    Madison has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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