Holiday rentals in Derby

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Top-rated holiday rentals in Derby

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

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Guest favourite
A charming log cabin is positioned near the water, surrounded by trees. The porch wraps around the front, featuring wooden railings. In the background, a river flows quietly, with a barge navigating its waters. A large rock is positioned in the foreground.
Cabin in Magnet
4.88 out of 5 average rating, 8 reviews

The Moondance

The “Moondance” will sleep six comfortably. The “Moondance” has 3 steps to the 1st floor. The 1st floor has a full kitchen, Dining room table that seats 6, one bedroom with a queen sized bed, full shower bath with washer & dryer. Upstairs the loft has a Queen bed, Full Bath. The living room has a queen sleeper sofa & TV with DVD player. Your doors walk out to your covered porch, with your grill & Hot Tub. Hot Tub FEE; $45. Pets are $45 per pet per night. Day guests (not overnight) are $10.00 ea.

Guest favourite
A modern structure with a blend of wood and stone features is situated along the riverbank. A spacious terrace surrounds a hot tub and an in-ground pool, offering unobstructed views of the Ohio River. The surrounding area is lined with trees, enhancing the natural setting.
Castle in Cannelton
4.93 out of 5 average rating, 14 reviews

NYA river front Lighthouse Castle

It's rare to find a place that's both historic and one-of-a-kind.Here you have it all, freshly renovated 4,000 sq/ft sleeps 20, in-ground summer pool and year around hot tub.Breath taking views of the Ohio River with plenty of to do inside and out. Enjoy our game room pool/pingpong table, shuffle board and darts along with a spectacular Ohio River view from each room! We are conveniently located 1 hour from Louisville,Owensboro and Evansville.Check us out NYAMillennial on ticktock and YouTube.

Top guest favourite
A modern cabin features a large deck surrounded by lush greenery, showcasing expansive glass windows that provide ample natural light. The structure has a sloped roof and is partially nestled among tall trees, highlighting the serene forest setting.
Cabin in New Pekin
4.96 out of 5 average rating, 101 reviews

Anjuna House - a Scandi riverfront forest getaway

Welcome to the enchanting retreat of "Anjuna," nestled among a sprawling forest in the heart of southern Indiana. This modern 4-bedroom, 3 bathroom luxury cabin features 14' floor-to-ceiling windows, and 1000+ sqft deck! Outside there are 12 acres of forest to explore, an outdoor shower and a tranquil river which meanders through the property. Anjuna is near Knobstone trail, Marengo Cave, and the bourbon trail in Louisville. Bring family, friends or just yourself to relax or explore at Anjuna!

Top guest favourite
A view from above captures a six-person hot tub with inviting blue water. Nearby, a circle of Adirondack chairs surrounds a fire pit, all nestled in a wooded area illuminated by warm string lights hanging overhead.
Cabin in Eckerty
4.98 out of 5 average rating, 158 reviews

Whitetail Woods cabin w/ HOT TUB and Patoka pass

Relax with the whole family at this peaceful cabin minutes from Patoka Lake entrance, winery, distillery, brewery, and dining! Perfect for family adventures, romantic getaways, ladies' weekends, and hunting trips. The cabin is located in peaceful Grant Woods surrounded by gorgeous Southern Indiana nature. You'll love relaxing in the 6-person hot tub, rocking on the covered front porch, and roasting marshmallows around the backyard fire pit. Cabin is a short drive to French Lick/West Baden.

Guest favourite
Cabin in Cannelton
4.92 out of 5 average rating, 255 reviews

Isaak's Hideaway -Beautiful Views for every season

Isaak's Hideaway is a spacious cedar log cabin with expansive windows overlooking the Ohio River and surrounded by Hoosier National Forest in Magnet, IN. Sleeping up to eight, this cabin is ready to entertain a houseful of family and friends. Enjoy the amazing river view and barge traffic while relaxing at the stone fire pit or lounging in the hot tub. Also, located about 50 minutes from Holiday World. Freshly painted with all new appliances! Also check out Pop's Hideaway - Magnet, IN.

Guest favourite
Cabin in Harned
4.89 out of 5 average rating, 18 reviews

Maple Cabin: Lakefront & Pet Friendly,3bed/1.5bath

Escape to the pet-friendly Maple Cabin, the perfect place to create vacation memories for families. With two bedrooms on the main floor and a cozy loft bedroom, there is plenty of room for everyone to unwind. This spacious cabin offers much needed serenity when escaping the stress of life. There is a gas grill for perfect summer burgers, a trolling boat for exploring the beautiful lake, and a picturesque hiking trail. End your day by the gas fireplace, enjoying the sounds of nature.

Guest favourite
Home in Hawesville
5 out of 5 average rating, 24 reviews

Meadowview

Keep it simple at this peaceful and centrally-located place. The house is right off the main highway. It is on a dead end street with only three houses and a beautiful meadow on the other side. The back deck makes it easy to sit and enjoy the view of the meadow. The living room and both bedrooms have televisions. Free Wifi and parking make this spot even sweeter. The home has a fully stocked kitchen and bathroom amenities. Memory foam mattresses make for a good night's sleep.

Top guest favourite
The exterior of the home features a light-colored facade with a welcoming front porch adorned with two chairs. A concrete driveway leads to a garage, while the neatly landscaped yard includes shrubs and mulch. Clear blue skies and soft clouds complete the serene outdoor setting.
Home in Brandenburg
4.99 out of 5 average rating, 116 reviews

Brandenburgs Favorite Airbnb

Over 100 guests agree..this 5 Star spotless home is perfect for vacation or business travel! Professionally designed for guests luxury and comfort, this Airbnb is rated in the top 1% of Airbnbs with all 5⭐️ Reviews. Enjoy the privacy of having the whole home, the comfy beds, the amenities and fluffy towels. Cook in the spacious kitchen with coffee bar, cookware, and spices. Relax in the outdoor spaces or watch the big TV's! This perfectly located home is one not to miss!

Guest favourite
The log cabin is set on a hillside surrounded by trees, featuring a red metal roof and large windows. A wooden deck leads to the entry, providing views of the Ohio River and nearby farmland. The natural setting contributes to a peaceful ambiance.
Cabin in Leavenworth
4.97 out of 5 average rating, 130 reviews

BIG TIMBER RIVER CABINS, "The Hawk's Nest"

The Hawk's Nest is a newly-built, authentic, hand-crafted log cabin with all the modern amenities. It sits on a bluff overlooking the Ohio River and serene Kentucky farmland. Located 5 minutes from I-64 in Crawford County Indiana, the cabin is easy to reach. The site is park-like & private, although not totally secluded. The cabin contains a full bath & kitchen. It also has heat/AC, TV, gas grill & private hot tub. Rent a cabin, relax, and watch the river boats float by!

Guest favourite
A rustic cabin constructed from wood and stone is nestled among trees, with a front porch featuring a railing. Sunlight highlights the natural surroundings, and fallen leaves cover the ground, creating a serene outdoor environment.
Cabin in Derby
4.95 out of 5 average rating, 275 reviews

Derby Escape

Welcome to the rolling hills of Southern Indiana. Your escape from the day to day grind awaits. Our cabin was built in the 1800's and reassembled (with modern conveniences) in 1996. Ideal for the hunter, hiker, boater or fisherman. Thousands of acres of Hoosier National Forest, the Ohio River and it's tributaries all provide a one of a kind outdoor recreation experience. Or you can just sit next to the fire, enjoy the night sky and relax! Either way... Welcome to Derby.

Top guest favourite
The interior of the cabin features a cozy living area with a plush sofa bed covered in a patterned quilt. A round area rug complements the wooden flooring, while a dining table with chairs is visible in the background, along with a small kitchen area equipped with essential appliances.
Cabin in Ferdinand
5 out of 5 average rating, 124 reviews

Eagle Pines Cabin (Eagle Adventures LLC)

Relax w/us at our beautiful, comfortable, and private Eagle Pines Cabin. We are 12 miles from Holiday World. The Cabin has its own private hot tub and also includes a private fire pit and we supply the firewood. Cabin is stocked with everything you’ll need. Hosts are on site, but out of sight. Our other rentals are Eagles Nest (3BR option) and Eagles Nest Plus (4BR option). Starting with the 2026 season check out will be at 10 am ON SUNDAYS ONLY, 11AM all other days.

Top guest favourite
Home in Saint Anthony
4.97 out of 5 average rating, 184 reviews

Hoosier Homestead in scenic southern Indiana

The Hoosier Homestead is nestled in the gently rolling hills of southern Indiana on historic Hoosier farmland. The beauty of southern Indiana is right outside the Homestead doorstep with scenic drives to numerous points of interest just minutes away. The Hoosier Homestead provides a cozy gathering space for your family and friends. Whether relaxing inside or counting stars by the fire bowl at night, everyone loves our Homestead. It is a great place to come together!

Popular amenities for Derby holiday rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Perry County
  5. Derby