Holiday houses in Jefferson County

A spacious great room features a modern sectional sofa positioned around a circular coffee table atop a vibrant area rug. Large windows allow ample natural light, illuminating the vaulted ceiling with exposed beams. Complementary artworks and plants enhance the inviting ambiance.

4.99 out of 5 average rating, 589 reviews

The Artist’s A-Frame

Get away and enjoy the comfort and convenience of this unique, newly remodeled A-Frame home nestled in a quiet, safe, upscale neighborhood, minutes from Clifty Falls State Park (10 min. drive), Historic Downtown (5 min. drive), hilltop shopping (5 min. drive): Hanover College (15 min. drive) •Fast Wi-Fi •Electric Fireplace .Two 55” Roku TVs, Complimentary YouTube TV for local and cable stations •Keurig & Drip Coffee, K-cups, local coffee, tea, bottled water .Paved driveway parking .Gas BBQ grill

HospitalityCleanlinessLocationComfortQuietDecorAmenitiesSleep qualityIndoor spacesKitchenNearbyAccuracyFamilyGetting aroundHikingCheck-inBathroomValueTVParksOutdoor spacesConditionCheckoutLaundryRiverWi-FiWalkabilityLayoutBarbecueBackyardAccessHeatingViewLong stayPoolEV chargingAir conditioningBikingNoise

A living area features a dark sofa adorned with scattered pillows, complemented by a wooden coffee table. Exposed brick walls bring a rustic charm, while large windows allow natural light to fill the space, showcasing views of the outside and nearby street.

4.98 out of 5 average rating, 101 reviews

The Main St. Oasis - Heart of Downtown Madison

Welcome to the Main St. Oasis in the heart of Historic Downtown Madison! We're steps away from Lanthier Winery, shopping, fine dining, the Ohio River, have a coffee shop right across the street, and a flower shop beneath you! Close to Clifty Falls State Park (3 min) & Hanover College (9 min). Enjoy a unique retro-western theme, with games & luxuries for all ages. Perfect for couples, families, or small groups. Ideal for exploring Madison’s top attractions or relaxing in comfort right on Main St!

LocationCleanlinessHospitalityWalkabilityDecorNearbyIndoor spacesComfortSleep qualityAccuracyKitchenParkingAccessAmenitiesBathroomQuietPetsFamilyRiverConditionViewParksHikingNoiseCheckoutValue

4.97 out of 5 average rating, 117 reviews

The kitchen area features a wooden countertop with a sink and an organized layout. Above, shelves hold various glassware and utensils, while a microwave and refrigerator are positioned nearby. Natural light enters through a window covered by light curtains, enhancing the space.

Guesthouse in Madison

Studio apartment above Garage in downtown Madison

This special place is located in downtown Madison. It's steps from restaurants and walking distance across all of downtown Madison. This above the garage apartment overlooks a koi pond and beautiful backyard of one of Madison's historic homes. Enjoy the beautiful balcony views and relax in this studio efficiency apartment with a pull out couch. Walking distance to gorgeous hiking destinations, including Clifty Falls State Park and the Heritage Trail. Come enjoy all that Madison has to offer!

HospitalityLocationCleanlinessComfortWalkabilityIndoor spacesOutdoor spacesSleep qualityNearbyGetting aroundQuietBreakfastAmenitiesAccuracyHikingParkingBackyardViewValueCheck-inDecorBathroomConditionTVParksLayoutFamilySolo travelAccessCheckoutBiking

The exterior of the home features a charming blue facade and a welcoming front door with a decorative glass accent. A brick pathway leads to the entrance, bordered by neatly trimmed greenery and potted plants. Lush shrubbery frames the property, enhancing its inviting appeal.

4.99 out of 5 average rating, 116 reviews

The Garden Home by Book Haven - Steps from Main

Spacious & stylish period home furnished like you’re traveling back in time - or escaping it. With an eclectic mix of decor from antique federalist style to fun MCM, the owners designed it to feel like a cozy library. Ready to see historic Madison? Walk 3 mins to Main St where you’ll find the Attic, Mad Love, Trolley Barn, & Olde Tyme. On Saturday mornings, take a 7-min stroll through Madison’s most stately brick homes down Third through Mill, Vine, Elm, and Broadway to the Farmer’s Market.

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A golf cart is parked on a well-maintained lawn in front of a cozy home. A shaded seating area with a thatched roof is visible, along with an outdoor dining set. A cornhole game is set up on the grass beside the cart.

4.9 out of 5 average rating, 101 reviews

Your Madison Home Away from Home

While staying in this cozy home, you can enjoy a peaceful morning with a small view of the Ohio River then use the golf cart to explore the historic town. Take a leisurely stroll along the Ohio River waterfront, visit the local winery, or indulge in the local restaurants and cafes nearby. Whether you're visiting Madison for a weekend getaway or a business trip, our home offers the perfect blend of comfort, convenience, and local charm. Book your stay today and make unforgettable memories.

Getting aroundLocationCleanlinessComfortHospitalityQuietSleep qualityAccuracyRiverNearbyIndoor spacesWalkabilityKitchenValueCheck-inAmenitiesBathroomParksViewOutdoor spacesDecorWi-FiParkingLaundryFamilyAccessTVBarbecueHikingLong stayBiking

4.99 out of 5 average rating, 272 reviews

The living room features a large sectional sofa facing a wooden coffee table and an electric fireplace. Natural light enters through two windows with light curtains, while a cozy armchair is positioned beside the fireplace, creating a relaxed atmosphere.

Townhouse in Madison

Cozy downtown home with patio. Walk to everything.

Your family will be close to everything in downtown Madison when you stay at this conveniently located, updated home built in 1880. First floor open concept floor plan includes living room equipped w/electric fireplace and an eat-in kitchen w/bar stool seating for 4. Upstairs offers two bedrooms and full bath w/shower and old old-fashioned soaker tub. Enjoy nice weather on the fenced back patio. Note: This property contains stairs and is not recommended for guests with mobility issues.

HospitalityLocationCleanlinessWalkabilityComfortNearbySleep qualityAmenitiesKitchenFamilyIndoor spacesBathroomAccuracyDecorQuietParkingHikingAccessBackyardConditionOutdoor spacesGetting aroundRiverCheck-inValueTVPetsLaundryAir conditioningBikingParksLong stayLayoutHeatingWi-FiSolo travelHot tubNoiseCheckout

A covered porch features a six-seat wrought iron dining set, providing a shaded space for outdoor gatherings. The flagpole displays the American flag against a clear blue sky. Surrounding greenery adds a touch of nature, enhancing the welcoming exterior of the home.

4.91 out of 5 average rating, 113 reviews

Bicentennial Park View

New June 2024! Full time Airbnb. Come stay at this newly renovated home in historic downtown Madison. This 3-bed/2-bath home is adjacent to Bicentennial Park and includes a fully stocked kitchen, washer & dryer, internet, keyless entry, front porch that overlooks the Ohio River and more. From the front porch of this home, enjoy the festivities of live concerts and Friday-night movies. You will enjoy easy access to everything Main Street offers from this centrally located home.

LocationWalkabilityCleanlinessHospitalityComfortNearbyFamilyParksIndoor spacesRiverPetsConditionParkingSleep qualityOutdoor spacesAmenitiesBathroomBackyardKitchenValueTVHeatingAccuracyHikingViewNoiseAccessAir conditioningCheck-inDecorGetting aroundPoolBeachCheckoutShared spaces

4.97 out of 5 average rating, 217 reviews

Riverview Historical Retreat

Full time Airbnb home in Historic Downtown Madison. This two bed, two bath home overlooks the Ohio River and includes a fully stocked kitchen, washer/dryer, screened in back porch, internet, keyless entry, and more Centrally located next to Bicentennial Park, enjoy one of the many restaurants, bars, parks, and local events, or enjoy a quiet weekend away with a weekly Music/Movie by the river, a local farmers market, and shops. There is something for everyone to enjoy in Madison

LocationWalkabilityViewCleanlinessHospitalityComfortRiverNearbyPetsBathroomIndoor spacesBackyardOutdoor spacesSleep qualityParksQuietAmenitiesKitchenDecorConditionFamilyAccuracyAccessHikingParkingCheck-inLayoutGetting aroundCheckoutPoolValueBiking

Superhost

Cottage in Madison

4.84 out of 5 average rating, 193 reviews

Cozy Cottage downtown *Pets*Trails*firepit*Clean

Sue’s Cottage is a quaint two bedroom cottage with a porch over looking the Heritage Trail of Madison. It is perfect for pets. It is a home to many species of birds and wildlife. Relax on the deck bird watching or stroll through the heritage trail & scenic railroad tracks surrounding the cottage, which leads to the river walk and Clifty Park. We are walking distance to all historic Madison offers. We are less than a mile from Clifty Park.

LocationHospitalityWalkabilityPetsNearbyCleanlinessHikingComfortQuietAccuracySleep qualityKitchenIndoor spacesFamilyParksBackyardOutdoor spacesValueGetting aroundBathroomCheck-inDecorRiverConditionAmenitiesWi-FiParkingCheckoutAir conditioningHeatingLaundryViewAccessTVLayoutLong stayBiking

The exterior of a charming shotgun house features a lavender-colored facade and a welcoming entrance. A small decorative plant is placed beside the steps, leading to a bright front door with a circular window above. Natural light enhances the inviting appearance.

4.98 out of 5 average rating, 135 reviews

Lavender House

Newly renovated shot gun house, great location in downtown Madison Indiana. Only one block from Main Street where there is shopping and restaurants, and four blocks from the river front. Two bedrooms each with a queen size bed, one bath, fully stocked kitchen, small private backyard. Washer and dryer on site, on street parking.This property is a shotgun style home which means you walk through one bedroom to get to the next, but there is a door between.

LocationCleanlinessHospitalityWalkabilityComfortDecorNearbyIndoor spacesQuietSleep qualityBackyardKitchenAmenitiesLayoutFamilyAccuracyCheck-inParkingConditionAccessCheckoutBathroomHikingGetting aroundWi-FiLaundrySolo travelLong stayRiverValue

4.99 out of 5 average rating, 102 reviews

Romantic & Private Retreat with hot tub

Escape to The Enchanted Cottage—a cozy, romantic retreat with a private hot tub, just 5 minutes from downtown Madison. Enjoy a king bed, rainfall shower, two 50” smart TVs, and a full-body massage chair. Sip from the coffee bar with flavored syrups or unwind with your cocktail setup. Relax on the covered deck or gather around the firepit (firewood available for purchase). Romantic add-ons available. ✨

HospitalityHot tubCleanlinessComfortLocationAccuracyOutdoor spacesDecorAmenitiesIndoor spacesSleep qualityKitchenViewNearbyGetting aroundValueQuietHikingCheck-inBarbecueConditionTVHeatingBreakfastCheckoutBathroomParksLayoutWi-FiParkingFamilyNoiseAir conditioning

4.99 out of 5 average rating, 238 reviews

The cabin features a rustic wooden exterior with a metal roof, surrounded by lush greenery. A wide porch with log railings offers a shaded area, and stairs lead up to the inviting entrance. Multiple seating options can be seen on the porch.

Cabin in Madison

Stoney Creek Cabin - Sit back and unwind

Welcome to Stoney Creek Cabin. This charming 2 bedroom cabin is nestled in the hills of Madison, IN. Situated far enough away to offer all the privacy you want, yet only 8 miles from historic downtown, where there are so many gems nearby to explore. Enjoy the HOT TUB, wrap around porch, and patio! There could not be a more relaxing place to unwind.

HospitalityCleanlinessLocationHot tubComfortOutdoor spacesNearbySleep qualityQuietIndoor spacesDecorAccuracyGetting aroundBarbecueAmenitiesKitchenFamilyHikingValueConditionViewBathroomRiverCheckoutParksCheck-inWalkabilityTVWi-FiNoiseAccessLayoutHeatingBackyard

Popular amenities for Jefferson County holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Jefferson County

4.9 out of 5 average rating, 215 reviews

A cozy kitchen area is highlighted, featuring dark cabinetry and modern stainless appliances. A large island made of reclaimed wood with stools for four sits in the foreground. Light streams in through a window, complementing the rustic decor and butcher block counters.

Cottage in Madison

Cozy Farmhouse Retreat in Historic District

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A wrought iron gate frames a vibrant garden filled with colorful flowers, including purple and pink blooms. A wooden chair is visible among the foliage, enhancing the tranquil outdoor space. The brick wall of the home provides a contrasting backdrop to the lush greenery.

4.95 out of 5 average rating, 188 reviews

Cozy 3 bedroom home, steps away from Main Street

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A spacious living area features a large sectional sofa in a neutral gray shade. The wall is adorned with a decorative mirror and a rustic wooden accent, while warm lighting enhances the inviting atmosphere.

5.0 out of 5 average rating, 335 reviews

Stablemaster’s Quarters/ Best downtown location!

HospitalityLocationWalkabilityCleanlinessDecorComfortNearbyIndoor spacesAmenitiesSleep qualityFamilyBathroomCheck-inKitchenAccuracyBreakfastRiverCheckoutQuietParkingTVHikingConditionParksGetting aroundValueLaundryAccessAir conditioningLayoutWi-FiLong stayPoolNoiseBiking

4.92 out of 5 average rating, 202 reviews

Home in Milton

Milton Hillton. River front home near Madison.

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An indoor pool area is showcased with a bright sky and floor-to-ceiling windows offering scenic views of the surrounding hills. The pool is surrounded by tiled flooring and potted plants, creating a serene setting. Skylights enhance the natural light within the space.

4.99 out of 5 average rating, 201 reviews

The Treehouse - Hot Tub - Indoor Pool Get Away!

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A bright living area showcases large windows with sheer curtains, allowing natural light to fill the space. A red front door adds a pop of color, complemented by a gray sectional sofa and a cozy armchair. A coffee table sits atop a patterned area rug, enhancing the inviting vibe.

4.99 out of 5 average rating, 127 reviews

Main Street Retreat

HospitalityLocationCleanlinessWalkabilityComfortSleep qualityNearbyAmenitiesDecorAccuracyQuietIndoor spacesParkingBackyardCheck-inParksCheckoutKitchenHikingGetting aroundOutdoor spacesBathroomBarbecueFamilyValueTVHeatingLaundryConditionNoiseAccess

4.98 out of 5 average rating, 46 reviews

The cabin exterior features a log construction with a sloped roof and a welcoming porch area. Several sturdy chairs are positioned on the porch, surrounded by neatly trimmed landscaping and a gravel pathway. Nearby trees provide a sense of tranquility to the outdoor space.

Home in Milton

The Madison-Milton Cabin

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The exterior of a classic two-story building is featured, showcasing a combination of stone and white siding. Black window frames create a modern contrast, while the entrance is marked by a decorative sign reading 'The Madison Inn Circa 1925,' supported by stone walls and lanterns.