Vacation rentals in Leopold

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Top-rated vacation rentals in Leopold

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Top guest favorite

Home in Leavenworth

Turkey Fork Creek Retreat

Turkey Fork Creek, our roomy retreat features a large yard for pets and children, outdoor games, and a secluded setting (10 acres). The expansive deck overlooking the woods is a guest favorite, an ideal place to unwind with coffee or cocktails while taking in the views. Inside offers an open layout, comfortable seating, and a fully equipped kitchen. Nearby, explore kayaking, hiking, and local dining, or relax on the patio. Perfect for gatherings, celebrations, or a quiet escape any time of year

FamilyLocationRiver

5.0 out of 5 average rating, 19 reviews

Guest favorite

The wooden cabin features a traditional design with a peaked roof and a red door. Surrounded by trees and under a clear sky, it is situated near the Ohio River, with gravel pathways leading to the entrance and an expansive view of the water visible in the background.

Cabin in Cannelton

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.

ValueFamilyWalkability

4.92 out of 5 average rating, 263 reviews

Guest favorite

Cabin in Derby

Whitetail Lodge, Twin Lakes Cabins

Welcome to Whitetail Lodge, an amazing two-story cedar retreat between two peaceful lakes in Southern Indiana located in our evergreen forest. Relax on the wraparound porches with beautiful water views, wildlife, and the sounds of nature. Perfect for couples, families, and friends, the lodge offers comfort, space, and memorable experiences. Enjoy paddle boats, kayaks, fishing, hiking trails, yard games, a private pavilion, fire pit and endless opportunities to unwind and reconnect outdoors.

ValueLocationQuiet

4.78 out of 5 average rating, 45 reviews

Top guest favorite

A spacious dining area features several wooden tables accompanied by comfortable chairs. Soft lighting is provided by ceiling fans overhead. Nearby, a cozy seating area includes a sofa and accent chairs, with a window allowing natural light to enhance the welcoming atmosphere.

Home in Evanston

Farm Stay with Sunset Views

This home is on a family farm in Spencer County, IN, just 15 minutes from Holiday World. It boasts open areas both inside and outside for family and friends to spend quality time together. We invite you to watch the cows graze and view the sunset from the back porch. Although the home is located on a rural gravel road, we are fortunate to provide fiber internet/WiFi and city water. The space comfortably sleeps 14 adults. 3 toddlers which don’t count toward occupancy. We offer 1 night stays

ValueLocationParking

4.99 out of 5 average rating, 149 reviews

Guest favorite

A single-story home is set on a grassy area surrounded by bare trees. The exterior features a combination of blue and red siding with a red metal roof. Neatly trimmed bushes frame the front, and a gravel path leads to the entrance.

Home in Evanston

The Patriot House

We would be delighted to welcome you to the Patriot House. This home is tucked away on 5 acres of dreamy countryside! It features a thoughtfully designed layout of 1,440 square feet and is the perfect mix of comfort and style. While the neighbors are nearby, they are far enough away to keep your secrets safe! Just a hop, skip, and a jump from Holiday World, 15 minutes away—and just 1.9 miles from Matilda’s wedding venue, it's the perfect getaway to relax and make unforgettable memories.

ValueLocationBackyard

4.95 out of 5 average rating, 55 reviews

Top guest favorite

A spacious living area features a high, sloped ceiling with track lighting. A mounted collection of deer antlers adorns the wooden walls. Comfortable seating is provided by a dark sofa and a cushioned chair, accompanied by a television and a rustic coffee table on a patterned rug.

Cabin in Grantsburg

Barndominium Lodge Getaway

Enjoy this spacious country setting inside and out . No steps, cabin is all on 1 level . Includes 1800+ sq. ft. and 2 car attached garage, 2 carports with plenty of parking. Covered porch, gas grill . Firepit /wood incl. Gathering area with picnic tables. 3 BR's 1 king , 1 queen, 1 full and 1 queen sofa sleeper. Fully equipped kitchen includes many cooking utensils plus dishwasher .Laundry room with washer & dryer. TV dish network DVD player with movies , shuffleboard & cornhole.

LocationFamilyIndoor spaces

4.98 out of 5 average rating, 45 reviews

Guest favorite

The exterior of a charming two-story brick home features a covered porch with a colorful bench. A large window complements the front door, which has an artistic design. The landscape includes open green space and a glimpse of a nearby vehicle.

Cabin in Branchville

Perry County Holiday World Hoosier Nat’l Forest

New remodel, located in the heart of the Hoosier National Forest in rural Perry County, Indiana. 30 minutes from Holiday World & Splashin' Safari! Outdoor enthusiasts will find an abundance of wildlife, trails, hiking, biking, horse backing, fishing, and boating. Atvs/utvs welcome and legal on county roads with a permit. Hunters welcome and bow season begins October 1. 60,000 Acres of Hoosier National Forest 476 Miles of county roads to travel on atvs, utvs, or side by sides

ValueFamilyIndoor spaces

4.97 out of 5 average rating, 29 reviews

Guest favorite

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

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.

FamilyLocationCheck-in

4.95 out of 5 average rating, 276 reviews

Guest favorite

A cozy living area features a plaid couch positioned next to an ottoman and a small side table. A wooden bench sits against the wall under a mirror. A television is mounted on the wall opposite the entrance door, with natural light illuminating the space.

Apartment in Hawesville

Highlander's Hidden Gem 1 Bedrm

Drive right up to your front door! There is only one other apartment sharing this location. Amenities include wifi, smart televisions in living room and bedroom, couch that folds out into a full size bed (pillows and blankets are in the ottoman in front of couch), eat in kitchen, and free parking. Even though this is a small town, there is a convenience store 1/2 block away, a Walmart that is 3 and 1/2 miles away, and two other local restaurants that deliver to your door.

ValueLocationComfort

4.97 out of 5 average rating, 100 reviews

Top guest favorite

An inviting living area features wooden beams and a stone fireplace. A comfortable sofa contrasts with a glass coffee table. The adjoining dining space is visible, showcasing a large window that allows natural light to illuminate the white dining table and chairs.

Farm stay in Dale

Iron Fence Farm - 2 miles from Holiday World

Forget your worries in this spacious and serene space. Newly renovated 6 bedroom, 4 bathroom house only 2 miles from Holiday World! This large vintage farmhouse can accommodate 21 people with its 6 bedrooms and 14 beds all linens included. Towels and toiletries included along with custom showers with rainfall shower heads. TVs in every bedroom. All new appliances including washer and dryer. Fully stocked game room with board games for every age. No pets allowed.

FamilyLocationNearby

4.96 out of 5 average rating, 99 reviews

Top guest favorite

A rustic log cabin with a two-story design is surrounded by lush greenery. The spacious front porch features wooden decking, outdoor furniture, and a hot tub, inviting relaxation. Large windows allow natural light to brighten the cabin's interior, offering views of the idyllic landscape.

Cabin in Derby

Derby Serenity

Looking to get away from the fast paced life? This cozy 2-story, 2 bedroom, 1.5 bath, rustic log cabin, sits on 4 acres tucked against the hills just outside Indiana's Hoosier National Forest in the Ohio River Valley. Kick back on the decks, relax in our hot tub, or watch the fire dance in the outdoor fire pit. Calm, tranquil, SERENITY!

LocationValueDecor

4.94 out of 5 average rating, 313 reviews

Top guest favorite

A restored log cabin features a white lap board exterior and a red metal roof. A stone foundation and a welcoming porch are visible. Nearby, a bell mounted on a wooden post stands beside a manicured lawn, surrounded by open crop land.

Cabin in Corydon

The Crecelius Cabin

Restored log cabin covered with white lap boards on outside is located on a county road in a rural community. 10 minutes from Historic Corydon with its many shops and sights to see with a Walmart near by. A small creek close by is great for canoeing, fishing and several caverns and wineries are in the area for you to enjoy.

ValueLocationKitchen

4.98 out of 5 average rating, 128 reviews