Pet-friendly vacation rentals in Jefferson County

4.93 out of 5 average rating, 61 reviews

The exterior of a historic log cabin is visible, surrounded by tall trees and lush greenery. The cabin features a covered porch and rustic wooden beams, blending harmoniously with the forested landscape. A gravel path leads to the front, enhancing the secluded atmosphere.

Cabin in Madison

Historic 1830s Log Cabin in Madison, IN

Beautiful historic 1830s log cabin nestled in the woods of Dugan Hollow! A 2-story cabin with 2 authentic lofted bedrooms with irregular shaped stairs as per the photos. Boasts a luxurious, oversized indoor jacuzzi tub for two. Uniquely situated only 5 minutes from Historic Madison, Indiana on the Ohio River; 15 minutes from Clifty Falls State Park; and 20 minutes from Big Oaks National Wildlife Refuge. *Small, housebroken dogs are allowed but must be crated if left alone in the Cabin.*

A cozy corner of the room features a light-colored armchair beside a wooden side table, with a potted plant nearby. A rustic dresser with a mirror is positioned against the wall, complemented by framed pictures and decorative items. Natural light filters through wooden-blind windows.

4.95 out of 5 average rating, 42 reviews

The Nature House

Historic home located in downtown Madison. Walking distance to all the shops, dining, and riverfront. The house is clean and beautifully decorated. Perfect for couples or groups. Modern kitchen with all the amenities you will need. Beautiful deck and patio out back with comfortable furniture and a fully fenced yard. The decor was inspired by Mother Nature and each room is decorated with gorgeous animal prints. Three bedrooms with comfortable mattresses and an office with a convertible couch.

4.86 out of 5 average rating, 134 reviews

The exterior of the cottage features light-colored siding and a wooden staircase leading to a deck. Lush greenery surrounds the base of the home, with slender trees and flowering plants visible. Large windows offer glimpses of the interior, while sunlight bathes the space.

Cottage in Madison

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. We are walking distance to all historic Madison offers. We are less than a mile from Clifty Park. A portion of each stay is donated to local charity.

4.94 out of 5 average rating, 51 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.

An outdoor dining area is visible, featuring a wooden table and benches set on a patterned rug. The table is neatly arranged with yellow placemats and glassware, while greenery can be seen in the background, enhancing the inviting outdoor environment.

4.99 out of 5 average rating, 69 reviews

Main Street - Heart of downtown Madison!

Main St is the HEART of Madison! We are centrally-located in downtown Madison. Our home is within walking distance for all of your downtown shopping adventures and the beautiful Riverfront. Start your mornings with a walk to one of our local coffee shops on your way to shop or enjoy a peaceful morning in of our amazing parks. Lunch and dinner can be their own adventure with all the local downtown eateries. Located only a few minutes away from the beautiful Clifty Falls State Park!

A gentle waterfall cascades over layered stone steps, surrounded by lush greenery and autumn foliage. The smooth flow of water creates a peaceful ambiance, inviting visitors to enjoy the natural beauty of the area.

5 out of 5 average rating, 75 reviews

Mulberry Manor*Walkable*8 Guests*4 Bed/2.5 Bath

Located in the Madison Historic District, close to everything when you stay at this centrally-located home. This gorgeous newly renovated home is located just a few blocks of bustling Madison Main Street, perfect place to stay with family/friends. Fully Equipped Kitchen, pots/pans/baking dishes/spices, cooking utensils, W/D, Free Reliable WiFi, dedicated workspace/desk/office chair, Smart TVs in 5 rooms, Premise Parking, Infant/Kid Friendly, 1 King, 2 Queens & 1 full futon-4th Bed.

An open living area is shown with a soft sofa and an armchair near large windows. A kitchen island with a wood countertop is positioned in the foreground, while a television and a washer are visible in the background. Natural light enhances the inviting space.

4.98 out of 5 average rating, 128 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

Superhost

Home in Deputy

4.82 out of 5 average rating, 22 reviews

Hardy Lake Vacation House

The House sits On Hardy Lake. 2 beds, 2 bath. Inside it has a full kitchen . The living room has queen sized sofa beds for extra guests. Gas grill and wood burning Fire pit, hot tub. Self-check-in. Smart TV that gets local channels. We provide board games, playing cards. Quiet getaway where guests can simply relax away from the city. 15 minutes from Scottsburg IN, 50 minutes from Louisville Ky. Lakeside Camping 4 min, Hardy Lake public Beach 15 min.boat parking space available

4.98 out of 5 average rating, 261 reviews

A charming stone patio is surrounded by lush greenery and colorful flowers. A large umbrella provides shade over a black metal table and chairs, inviting relaxation. A decorative circular stone is positioned nearby, complementing the natural landscape.

Guesthouse in Madison

Mulberry Cottage In The Heart Of Downtown Madison

This quaint studio cottage is located in the heart of Madison, Indiana. The entire building was fully renovated in 2020 and offers a modern luxurious stay in our beautiful historic town. This property features off-street parking, fast private WiFi, and complimentary beverages/snacks. Within walking distance of shopping, restaurants, and all downtown events. Few properties come close to the accessibility that this Madison cottage provides. We look forward to hearing from you!

The image captures a softly lit entrance area, featuring the number '404' on a glass panel. A delicate lace curtain filters natural light, creating gentle shadows on the wall, which is painted in a light, neutral colour.

4.95 out of 5 average rating, 41 reviews

The Cozy Couch

You will be close to everything when you stay at this centrally-located home. This beautiful and spacious historic home built by Francis Costigan and located by Francis Cositgan's historical home. You are just steps away from the Broadway Fountain, downtown shopping, and only a few blocks away from the Ohio River. This three bedroom, 1 ½ bath home boasts tall ceilings and large rooms which makes it a great place to stay with family or friends.

4.96 out of 5 average rating, 51 reviews

A cozy living room features a brown leather sofa with decorative pillows, accompanied by a wooden coffee table. A cowhide area rug lays on the tiled floor, adding texture. A light-colored chair and a small wooden stool complete the inviting space, with natural light entering through a large window.

Home in Hanover

The Hanover Hideaway

Discover the perfect retreat in Hanover, less than a mile from Hanover College, minutes from Clifty Falls State Park, 6 miles to the Ohio River Boat Ramp & less than 10 minutes to Historic Downtown Madison. This 3-bed, 2-bath home embodies modern Western design, offering comfort and style. Ideal for extended trips or weekend getaways. Whether you're here for academia or leisure, we promise you will enjoy your stay at the Hanover Hideaway!

A semi-private outdoor area features stylish Adirondack chairs and a small table, situated on a wooden deck. A comfortable seating area is arranged against the wall, and a decorative pumpkin adds a seasonal touch. A grill and steps lead to the entrance of the house.

5 out of 5 average rating, 18 reviews

Annies Fabulous Federal house

Annies Fabulous 1850 Federal house is just blocks from the majestic Ohio River, shopping, eateries and wineries! Step out the front door and be a part of the largest historic district in Indiana! Annies Fabulous Federal house has fabulous upgrades, fabulous decor, and a semi -private back yard! We allow canines! $50.00 upcharge for your dog will be added.

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What guests are saying

The Baltmore

5 out of 5 average rating, 27 reviews1 day ago

My husband and I really enjoyed our stay at The Baltmore. The house was immaculate, and the decor was so tastefully done. From the local artists artwork throughout the house, the comfortable and cozy furniture, most from local vendors and shops in Madison, and the special decorating touches that made you feel right at home. The booklet that she put together had not only great suggestions for restaurants and things to see and do in Madison but also had the history of the house. The neighborhood was very quiet and close to absolutely everything in Madison. We loved sitting out on the back deck just enjoying the pleasant evenings. Andra was an incredible host, by far one of the best I have ever dealt with on Airbnb. She was so helpful and always responded to my emails very quickly. She definitely does what it takes for you to be comfortable and feel like you're in your own home. I highly recommend it if you're planning a trip to Madison, IN.

Home in Madison

What guests are saying

Historic Madison Retreat - 1 Mi to Ohio River

4.67 out of 5 average rating, 9 reviews16 months ago

We loved this cottage and the freedom it gave us to bring our fur babies with us. We got to spend time with family and even were able to invite family to come to us for a game day. It was lovely and I would highly recommend this cottage to anyone looking for a home away from home.

Cottage in Madison

What guests are saying

Walk to Main St- Cozy Beds/Clean!

4.93 out of 5 average rating, 54 reviews4 months ago

Our stay at the Airbnb in Madison, Indiana was delightful. The place exuded a warm, inviting atmosphere with a touch of local charm that made us feel right at home. The location was perfect, providing easy access to explore the historic downtown and the scenic Ohio Riverfront. The host (Brooke) was incredibly accommodating, offering great local tips and ensuring we had everything we needed for a comfortable stay. The decor was tasteful, blending modern comfort with the town’s rich history, making our weekend getaway memorable and relaxing. Highly recommended for anyone looking for a serene and authentic experience in Madison!

Home in Madison

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Popular amenities for Jefferson County pet-friendly home rentals

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Pet-friendly house rentals

A cozy living room featuring a warm-toned sofa complemented by decorative cushions. There are built-in shelves displaying various artistic items and photographs. Natural light pours in through a window, highlighting a soft area rug on the floor, and wooden elements add a touch of comfort.

4.75 out of 5 average rating, 8 reviews

Fiona’s Boho Retreat

Superhost

A spacious dining area features multiple wooden tables surrounded by chairs, some with red upholstery. A chandelier provides overhead lighting, and a plush mat lies beneath the tables. Light green walls create a calming environment, while a doorway leads to another room.

4.73 out of 5 average rating, 15 reviews

JPG Officer's Quarters

4.96 out of 5 average rating, 82 reviews

Home in Deputy

The Cottage by the Woods

The exterior of a renovated home features a welcoming porch with a swing. A fenced yard is visible, alongside a small outdoor seating area. Lush green grass and landscaping frame the entrance, while sunlight brightens the façade, highlighting the charming exterior.

5 out of 5 average rating, 37 reviews

2 King Beds-1 Block to Main St-Downtown Cottage!

An open living area features a gray sectional sofa and a wooden coffee table, complemented by a cozy armchair. Exposed brick walls add character, while large windows offer natural light. A dining area with black chairs and a kitchen area with dark fixtures can be seen in the background.

5 out of 5 average rating, 73 reviews

Walnut Street Saloon BNB

A modern living area features comfortable seating and a large television mounted on the wall. A round coffee table sits on a patterned rug, while a kitchen area with sleek appliances and an island with barstools is visible in the background. Natural light enters through a nearby window.

5 out of 5 average rating, 4 reviews

Long or Short stay-King beds

The living area features a cozy arrangement with a dark gray sofa and an armchair, accented by colorful throw pillows. A plush area rug with a striped design covers the wooden floor. Music-themed decor adorns the walls, complemented by a potted plant beside a wooden cabinet.

4.9 out of 5 average rating, 52 reviews

• Rhythm&Blues • *Pets welcome*Golf Cart available

A welcoming living area features a comfortable chair and a stylish coffee table. A large television is mounted on a light-colored wall adorned with a decorative clock. Natural light enters through tall windows, complemented by flowing drapes and a decorative plant nearby.

New place to stay

Aquantis

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Pet-friendly home rentals with a pool

4.98 out of 5 average rating, 47 reviews

Home in La Grange

Lux Heated Saltwater Pool + Games/Firepit/Hot Tub

4.87 out of 5 average rating, 38 reviews

The living room features a light-colored sofa and armchair, complemented by wooden side tables. A large wall-mounted TV and a ceiling fan are visible, along with a plush area rug. Natural light comes from the door leading to an outdoor space.

Condo in Crestwood

Luxury Apartment/Near Louisville/EV Charger

4.91 out of 5 average rating, 34 reviews

A wooden swing seat is positioned on a concrete patio, featuring striped cushions in red and white. The cozy seating area is bordered by rustic walls and stonework, creating a serene outdoor retreat. Sunlight casts gentle shadows across the space.

Home in Aurora

"French Riviera" Long Term Discounts

4.92 out of 5 average rating, 65 reviews

The exterior of a spacious home is shown, featuring a large, fenced backyard with a well-maintained green lawn. Several trees are visible nearby, and the structure has a combination of traditional and modern architectural elements, including a sloped roof and multiple windows that invite natural light.

Home in Aurora

Unique Luxury Family Retreat

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Private, pet-friendly home rentals

5 out of 5 average rating, 66 reviews

An oversized clock sculpture adorned with the phrase 'OFF THE CLOCK' is featured in the foreground. Surrounding landscaping includes planters with various plants. The riverfront property is visible in the background, complemented by a deck and string lights overhead.

Guest suite in Hanover

OFF THE CLOCK River House

KylieRating, 5 stars6 months ago

Amazing hosts! Great place with a beautiful view! Incredibly friendly and helpful and we had the best time! Thank you!!

A charming shotgun style home features a light blue exterior with white trimming and a covered front porch. The porch is adorned with plants and a small seating area. A pathway leads to the entrance, framed by a neat garden and wrought iron railing.

5 out of 5 average rating, 27 reviews

The Baltmore

CaroleRating, 5 stars1 day ago

My husband and I really enjoyed our stay at The Baltmore. The house was immaculate, and the decor was so tastefully done. From the local artists artwork throughout the house, the comfortable and cozy furniture, most from local vendors and shops in Madison, and the special decorating touches that made you feel right at home. The booklet that she put together had not only great suggestions for restaurants and things to see and do in Madison but also had the history of the house. The neighborhood was very quiet and close to absolutely everything in Madison. We loved sitting out on the back deck just enjoying the pleasant evenings. Andra was an incredible host, by far one of the best I have ever dealt with on Airbnb. She was so helpful and always responded to my emails very quickly. She definitely does what it takes for you to be comfortable and feel like you're in your own home. I highly recommend it if you're planning a trip to Madison, IN.

4.86 out of 5 average rating, 134 reviews

Cottage in Madison

Cozy Cottage downtown *Pets*Trails*firepit*Clean

4.98 out of 5 average rating, 261 reviews

Guesthouse in Madison

Mulberry Cottage In The Heart Of Downtown Madison