Best Vacation Homes in Jefferson County
Cabin
10.0(224 Reviews)
1 Bedroom
1 Bath
4 Guests
Parking
Ocean View
Balcony/Terrace
View
R3,330/Night
7 Nights - R23,308
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
1603.82 ft²
Hot Tub- Parking
- Balcony/Terrace
Air Conditioner
R3,929/Night
7 Nights - R27,497
House
9.4(148 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
Pool- Balcony/Terrace
R2,455/Night
7 Nights - R17,194
Cabin
10.0(124 Reviews)
2 Bedrooms
1 Bath
5 Guests
800 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
R3,341/Night
7 Nights - R23,389
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
Child Friendly
Security/Safety
R2,863/Night
7 Nights - R20,041
Apartment
10.0(87 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Parking
- Ocean View
- View
Kitchen
R3,756/Night
7 Nights - R26,284
House
10.0(74 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R4,762/Night
7 Nights - R33,337
House
10.0(47 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Breakfast
- Parking
- Ocean View
R4,660/Night
7 Nights - R32,625
Jefferson County Luxury Rentals
Cabin
10.0(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
1617 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
Internet
R13,288/Night
7 Nights - R93,006
House
9.4(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R12,165/Night
7 Nights - R85,161
House
9.0(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1603.82 ft²
- Hot Tub
- Parking
- Air Conditioner
- Internet
R12,110/Night
7 Nights - R84,773
House
4 Bedrooms
4 Baths
14 Guests
1614.59 ft²
- Air Conditioner
- Internet
- Child Friendly
Sports/Activities
R11,809/Night
7 Nights - R82,670
House
10.0(2 Reviews)
5 Bedrooms
4 Baths
16 Guests
3270 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R11,777/Night
7 Nights - R82,444
Cabin
10.0(1 Review)
4 Bedrooms
3 Baths
14 Guests
1617 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
R10,342/Night
7 Nights - R72,399
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R9,821/Night
7 Nights - R68,744
House
10.0(64 Reviews)
4 Bedrooms
3 Baths
12 Guests
3500 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
R8,929/Night
7 Nights - R62,500
Jefferson County Pet Friendly Vacation Rentals
Apartment
10.0(40 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R3,406/Night
7 Nights - R23,842
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
796.53 ft²
- Parking
Spa- Balcony/Terrace
- Internet
R2,766/Night
7 Nights - R19,361
House
10.0(30 Reviews)
2 Bedrooms
1 Bath
4 Guests
1166 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R4,167/Night
7 Nights - R29,163
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1162.5 ft²
- Parking
- Balcony/Terrace
- Internet
Pet Friendly
R3,370/Night
7 Nights - R23,583
House
10.0(20 Reviews)
2 Bedrooms
2 Baths
8 Guests
1635 ft²
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
R6,013/Night
7 Nights - R42,087
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
8 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
R5,887/Night
7 Nights - R41,214
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R5,015/Night
7 Nights - R35,100
House
9.8(67 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,460/Night
7 Nights - R24,214
Jefferson County Large Vacation Homes
House
10.0(71 Reviews)
5 Bedrooms
3 Baths
10 Guests
2200 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R5,242/Night
7 Nights - R36,685
Apartment
6.5(2 Reviews)
5 Bedrooms
8 Baths
20 Guests
1407.92 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
R3,497/Night
7 Nights - R24,473
Cabin
10.0(67 Reviews)
4 Bedrooms
2 Baths
12 Guests
2040 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R4,176/Night
7 Nights - R29,228
House
10.0(43 Reviews)
5 Bedrooms
3 Baths
10 Guests
2200 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R6,546/Night
7 Nights - R45,824
House
10.0(1 Review)
3 Bedrooms
4 Baths
10 Guests
2800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R5,511/Night
7 Nights - R38,577
House
9.8(21 Reviews)
5 Bedrooms
3 Baths
8 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
R7,684/Night
7 Nights - R53,782
Cottage
10.0(10 Reviews)
2 Bedrooms
1 Bath
100 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,874/Night
7 Nights - R27,109
Apartment
10.0(7 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Child Friendly
- Security/Safety
R15,853/Night
7 Nights - R110,977
Why Choose Rent By Owner for your Jefferson County Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Jefferson County
When should you plan your Vacation Rentals stay?
Timing your visit to this destination can enhance your experience, so consider seasonal patterns and local events when choosing the best time to book your vacation rentals in Jefferson County for an unforgettable stay.
Peak Season Highlights
Spring (March to May)
During spring, the area comes alive with blooming flora and pleasant weather, making it an ideal time for outdoor activities and exploring local scenery.
Average Temperature Daytime: 60-75°F - Nighttime: 40-55°F
Fall (September to November)
Autumn offers striking fall foliage and cooler temperatures, perfect for scenic drives and enjoying the natural beauty of this destination.
Average Temperature Daytime: 55-70°F - Nighttime: 35-50°F
Off-Season Highlights
Summer (June to August)
The summer months bring warmer weather, attracting visitors seeking outdoor adventures and recreational activities in the region.
Average Temperature Daytime: 80-90°F - Nighttime: 60-70°F
Winter (December to February)
In winter, the area experiences colder temperatures, offering a quieter environment and opportunities for seasonal indoor pursuits.
Average Temperature Daytime: 30-45°F - Nighttime: 20-30°F
Weekly Weather Forecast for Jefferson County
How to Book Your Jefferson County Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor space with a spacious patio or deck for relaxing and entertaining.
- Take advantage of a fire pit area perfect for evening gatherings under the stars.
- Explore nearby walking trails or nature paths directly from your rental property.
- Make use of outdoor dining areas to savor meals while soaking in the scenic views.
- Benefit from access to a well-maintained swimming pool during warmer months.
- Relax in hammock stations or lounge chairs set up in the yard or garden.
- Participate in outdoor recreational activities such as kayaking or fishing if available nearby.
Top Attractions Around Jefferson County
What attractions are nearby?
Enjoy a variety of outdoor activities, scenic parks, and cultural experiences just moments from your stay in this charming region, offering endless opportunities to explore nature and local heritage during your visit.
Family Activities
- Clifty Falls State Park: Explore scenic waterfalls, hiking trails, and family-friendly picnic areas nestled within this natural gem of the region.
- Jefferson County Historical Museum: Discover the area's rich heritage through engaging exhibits that offer an educational experience for visitors of all ages.
- Blue River: Enjoy outdoor adventures like fishing, kayaking, or simply relaxing along the gentle currents of this nearby river in the region.
- Madison Historic District: Stroll through charming streets filled with preserved 19th-century architecture, perfect for a family afternoon of sightseeing.
Adult Activities
- Exploring the historic sites and museums: You can discover the rich history of this area by visiting its well-preserved museums and historic landmarks.
- Enjoying outdoor recreation at local parks and trails: Take advantage of the scenic parks and extensive trail systems to hike, bike, or simply relax in nature here.
- Savoring regional cuisine at local eateries: Indulge in authentic dishes and regional specialties that showcase the culinary charm of this destination.
- Participating in cultural events and festivals: Engage with the vibrant community through seasonal festivals and cultural festivities held throughout the area.
Other Places to Stay in Jefferson County, IN
Brooksburg
Hanover
Historic Eleutherian College
Chelsea
King's Daughters' Health
Madison
Sunrise Falls Golf Course
Francis Costigan House
Dr. William Hutching's Office & Hosptal
Historic District
Jeremiah Sullivan House
Canaan
Jefferson County Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Make the most of your stay by visiting the area's renowned sites and natural beauty to immerse yourself in its unique charm.
- Plan Outdoor Activities: Take advantage of nearby parks and outdoor spots for hiking, fishing, or picnicking to enjoy the region’s scenic landscapes.
- Enjoy Authentic Cuisine: Seek out local dining experiences that highlight regional flavors and culinary traditions during your visit.
- Utilize Nearby Amenities: Maximize convenience by choosing accommodations close to essential services and entertainment options in the destination area.
Transportation Options
- Interstate 65: You can access this major highway for convenient road travel to and from the area, connecting you easily to regional destinations.
- Louisville International Airport: This nearby airport offers flights that make traveling into the region quick and straightforward for visitors arriving from afar.
- Local Bus Services: Regional bus options provide an affordable way to explore here without the need for a car, ideal for short-distance travel within the area.
- Taxi and Rideshare Services: Reliable transportation options like taxis and rideshares are available for flexible travel around the destination and its surroundings.
Local Customs Options
- Local Festivals and Events: Participating in the region’s annual festivals offers a glimpse into the community's traditions and history.
- Seasonal Hunting and Fishing Traditions: Engaging in hunting or fishing activities is a respected custom here, reflecting the area's natural resources and outdoor lifestyle.
- Historical Preservation Practices: Respect for historical sites and preservation efforts highlight the community’s commitment to maintaining its heritage.
- Local Art and Craftsmanship: Supporting local artisans by exploring craft fairs and markets showcases the region’s unique artistic traditions.
Frequently Asked Questions About Jefferson County?
1. What are the top vacation rentals in Jefferson County?
There are a lot of options in Jefferson County. If you plan on staying in the Jefferson County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Jefferson County:
- 1800’s restored log cabin on 26 private rolling wooded acres with sunset views
- The Chandler Hotel
- Stoney Creek - Sit back and unwind
- Best downtown location! Stablemasters Quarters is awarded winning! Come see why…
- The Wadsworth in National Historic District of Madison, Indiana.
- #209 Kings, River View, Deck, Bicentennial Park
- Rustic cabin just outside of Madison!
- Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
- Beautiful and spacious 3BR historic home centrally located in downtown, Madison.
- The Cypress Grove Inn ~Madison, IN! *5 Star hosts!
2. Which vacation homes in Jefferson County are best for families?
If you are looking for a family-friendly vacation home in Jefferson County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Jefferson County:
3. How many Rentbyowner vacation rentals are available in Jefferson County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 159 in the Jefferson County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Jefferson County.
4. What is the cancellation policy for vacation rentals in Jefferson County, Indiana?
The cancellation policy varies by property. To view specific details and any applicable fees or restrictions, please refer to the listing or contact the host directly.
5. How do I find available dates and secure my stay in a vacation rental here?
You can check availability and make reservations through the property’s booking page. For assistance or special requests, reaching out to the owner can help ensure your plans align perfectly.
6. Are there any rules or restrictions I should be aware of before booking?
Each property may have its own house rules regarding noise, pets, or accommodations. It’s best to review these details on the listing or communicate with the host to clarify expectations.
7. What amenities are typically included in vacation rentals around this destination?
Amenities vary by property but often include essentials like Wi-Fi, parking, and kitchen facilities. To confirm specific features, please review the property listing or contact the owner directly.
8. Is there a minimum stay requirement for booking here?
Minimum stay requirements depend on the individual property. Details are listed on each property page, and contacting the owner can provide further clarification if needed.
Jefferson County Top Rated Vacation Rentals
House
9.8(85 Reviews)
2 Bedrooms
2 Baths
5 Guests
900 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R3,739/Night
7 Nights - R26,171
Hotel
8.7(328 Reviews)
11 Baths
172.22 ft²
Oceanfront- Parking
- Pool
- Ocean View
R2,264/Night
7 Nights - R15,851
Hotel
8.3(620 Reviews)
6 Baths
468.23 ft²
Private Pool- Breakfast
EV Charge Station- Parking
R1,878/Night
7 Nights - R13,150
Hotel
8.3(246 Reviews)
1 Bath
321.57 ft²
- Private Pool
- Breakfast
- EV Charge Station
- Parking
R1,801/Night
7 Nights - R12,600
R1,469/Night
7 Nights - R10,287
Hotel
7.0(277 Reviews)
1 Bath
21.53 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R1,278/Night
7 Nights - R8,945
House
10.0(116 Reviews)
1 Bedroom
2 Baths
2 Guests
- Breakfast
- Parking
- Pool
- Spa
R2,129/Night
7 Nights - R14,897
House
3.0(2 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
R2,345/Night
7 Nights - R16,418
