Madison vacation rentals

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Top-rated vacation rentals in Madison

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Apartment in Madison

4.99 out of 5 average rating, 199 reviews

Rivers Edge-Historic Hunger House-Upstairs-Madison

A unique blend of historic character and contemporary comfort! Floor to ceiling windows, amazing staircase and hardwood flooring with modern kitchen & bathroom, this UPSTAIRS unit with private entrance will be your oasis. The balcony, w/view of the Ohio river, is perfect for early morning coffee or relaxing after a busy day of touring Madison. WELCOME to the River's Edge! Extended stay (week-mo) discounts 21%-49%. Rent one or both floors (See "River's Edge II-listing) SEND INQUIRY FOR PRICING

Feb 23 – Mar 2

G$19,486 GYD per night
Guest favorite

Tiny home in Madison

4.93 out of 5 average rating, 135 reviews

TINY TOO

A Tiny house located in historic Madison, Indiana. Tiny Too is located in the heart of the history of this beautiful river town. Located just steps from the Ohio River, Heritage Trail, quaint shops, local restaurants, wineries and a host of festivals. Step outside the upper and lower decks to river views. Our property is newly remodeled and equipped with all of the amenities of home PLUS outdoor seating (upper/lower decks), gas grill and bicycles. It also offers private, off street parking.

Nov 7 – 14

G$20,936 GYD per night
Guest favorite

Apartment in Madison

5.0 out of 5 average rating, 269 reviews

Stablemaster’s Quarters/ Best downtown location!

The historic building was originally one of the city’s main livery stables circa 1886. New very comfortable furnishings, a spacious gathering area, 2 large bathrooms, a laundry room and a furnished white kitchen will all be appreciated. Carefully, the historic charm is blended within. You will soon see why the entire building is award winning! This fun river town will remind you of years gone by. Come see why Ladie’s Home Journal awarded Madison “ prettiest small town in the Midwest”.

Nov 6 – 13

G$39,166 GYD per night

Popular amenities for Madison vacation rentals

Stay near Madison's top sights

The Red Pepperoni26 locals recommend
Hinkle's Sandwich Shop17 locals recommend
Key West Shrimp House8 locals recommend
Kroger6 locals recommend
Off Broadway Tap Room20 locals recommend
Bicentennial Park3 locals recommend

Other great vacation rentals in Madison

Guest favorite

Home in Madison

4.98 out of 5 average rating, 134 reviews

The Crafty Fox Den - Retreat House

May 17 – 24

G$54,164 GYD per night
Guest favorite

Farm stay in Goshen

4.98 out of 5 average rating, 282 reviews

The Coop

Nov 24 – Dec 1

G$23,867 GYD per night
Guest favorite

Home in Bedford

4.99 out of 5 average rating, 185 reviews

Atoka Farms

Aug 28 – Sep 4

G$28,989 GYD per night
Guest favorite

Guesthouse in Madison

4.94 out of 5 average rating, 50 reviews

Studio apartment above Garage in downtown Madison

Apr 20 – 27

G$18,360 GYD per night
Guest favorite

Home in Madison

5.0 out of 5 average rating, 24 reviews

The Book Haven - A Book Lover's getaway near Main

Feb 14 – 21

G$28,076 GYD per night
Guest favorite

Home in Madison

4.94 out of 5 average rating, 32 reviews

Your Madison Home Away from Home

Nov 6 – 13

G$27,229 GYD per night
Guest favorite

Bungalow in Madison

4.97 out of 5 average rating, 34 reviews

Spacious 2 bedroom 1.5 bath home in Downtown.

Dec 17 – 24

G$30,928 GYD per night
Guest favorite

Home in Madison

4.97 out of 5 average rating, 59 reviews

Lavender House

Aug 6 – 13

G$26,820 GYD per night
Guest favorite

Apartment in Madison

4.97 out of 5 average rating, 36 reviews

The Treehouse - Hot Tub - Indoor Pool Get Away!

Nov 4 – 11

G$36,082 GYD per night
Guest favorite

Home in Madison

4.93 out of 5 average rating, 82 reviews

Cozy 3 bedroom home, steps away from Main Street

Jul 27 – Aug 3

G$31,184 GYD per night
Guest favorite

Cottage in Madison

4.94 out of 5 average rating, 49 reviews

Riverfront Cottage downtown Madison

May 7 – 14

G$33,453 GYD per night
Guest favorite

Home in Madison

4.93 out of 5 average rating, 74 reviews

Lanier View ll (Perfect for Social Distancing)

May 17 – 24

G$30,761 GYD per night

Other great vacation rentals in Madison

Guest favorite

Home in Milton

5.0 out of 5 average rating, 11 reviews

The Madison-Milton Cabin

Nov 10 – 17

G$32,526 GYD per night
Guest favorite

Guesthouse in Madison

4.91 out of 5 average rating, 64 reviews

The Goataway

Apr 11 – 16

G$22,579 GYD per night
Guest favorite

Tiny home in Milton

4.84 out of 5 average rating, 74 reviews

The Rustic River Retreat.

Nov 29 – Dec 6

G$27,742 GYD per night
Guest favorite

Cabin in Madison

4.99 out of 5 average rating, 76 reviews

Wolf Creek Cabin

Mar 9 – 16

G$40,150 GYD per night
Guest favorite

Cottage in Madison

5.0 out of 5 average rating, 26 reviews

3-suite cottage spa (aaaah!) house

Oct 24 – 31

G$62,142 GYD per night
Guest favorite

Cabin in Vevay

4.97 out of 5 average rating, 59 reviews

The Cabin

Mar 10 – 17

G$21,196 GYD per night
Guest favorite

Home in Madison

4.93 out of 5 average rating, 28 reviews

• Rhythm & Blues • *Golf Cart Available

May 13 – 20

G$27,157 GYD per night
Guest favorite

Home in Madison

5.0 out of 5 average rating, 72 reviews

The Row House

Apr 26 – May 3

G$38,649 GYD per night
Guest favorite

Home in Vevay

4.92 out of 5 average rating, 51 reviews

Riverside cottage sleeps 4

Apr 21 – 28

G$25,645 GYD per night
Guest favorite

Home in Madison

5.0 out of 5 average rating, 60 reviews

Watchmaker Place in Historic Madison District

Apr 13 – 20

G$54,164 GYD per night
Guest favorite

Loft in Madison

5.0 out of 5 average rating, 19 reviews

East Main Lofts - Coastal 201

May 31 – Jun 7

G$29,077 GYD per night
Guest favorite

Home in Madison

5.0 out of 5 average rating, 80 reviews

Vineyard Château - peaceful country setting!

May 20 – 27

G$40,699 GYD per night

Quick stats about vacation rentals in Madison

Total rentals

100 properties

Wifi availability

100 properties include access to wifi

Rentals with dedicated workspaces

50 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

70 properties are a good fit for families

Total number of reviews

6.8K reviews

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Madison?

    Four-legged friends are welcome in Madison. Choose from more than 20 vacation rentals for guests traveling with pets.

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

    Yes! Work meets play with ease at over 50 vacation rentals in Madison featuring dedicated workspaces. Stay connected and productive in your home away from home.

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

    Experience the best of Madison with our house rentals, starting at about $20 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 air conditioning?

    Absolutely! We offer over 50 house rentals with air conditioning in Madison. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Madison?

    Madison has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Madison have wifi?

    Absolutely! We offer over 50 house rentals with wifi in Madison. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Madison have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Madison. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Madison?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with air conditioning, over 10 homes with a bbq area, over 50 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Indiana
  4. Jefferson County
  5. Madison