
Holiday rentals in Jennings
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Top-rated holiday rentals in Jennings
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NAMASTE Lofts - Downtown Greencastle!
Looking for peace and serenity in the heart of downtown Greencastle, welcome to Namaste Lofts! We provide 2 distinctively designed lofts that exude a sense of calmnessin the bustling downtown. Each unit reflects the architectural features from the 1800’s, but the eclectic design with a mix of urban & modern furnishings makes the lofts a one of a kind place to stay. Located on the north side of Greencastle’s downtown square, you are walking distance to all entertainment, and DePauw University.

Peaceful apartment space in beautiful farm house
Our lovely farmhouse is minutes from Lake Lemon, Griffey Lake, Indiana University & many spots in Bloomington. Conveniently not far from I-69, we're 20 minutes away from Nashville. This is a basement apartment with private bedroom, private bathroom, large living/dining area, & kitchenette. Shared front door & ~10 steps inside main floor. The ranch is 50+ acres with 8+ acres of woods for hiking, pastures with cattle, a heated pool & patio area, & a beautiful front porch looking over the ranch.

Waterfront getaway *cozy & peaceful*fishing*swings
Welcome to your peaceful lakeside getaway! This renovated boho-style cottage offers a quiet and laidback retreat. Featuring an open loft layout, a covered porch, and a large deck overlooking two small serene lakes, this home is designed for relaxation. Enjoy evenings under the Pergola with swings or gather around the hillside firepit for unforgettable nights. Its location also makes it easy for you to get around. You're just: 10 min to I-70 hwy 20 mins to the airport 30 mins to Indy Downtown

A room with view - great location
This room is a good value. It is close enough to Indianapolis yet peaceful, clean, quiet, and private. We are: 7.1 miles (10 minutes) from Indianapolis international airport. 18 miles (26 minutes) from downtown Indianapolis, 17miles (20 min drive) from Indianapolis convention center and Lucas stadium. 35 miles (52 minutes) from Indiana University in Bloomington. ~3 miles from I-70. If interested in booking please answer our pre booking questions found at the beginning of the house rules.

Cataract Lake Getaway - Cozy Lofted Cabin (#2)
This brand new cabin on a private road is a serene setting perfectly blending rustic charm and modern comfort. Only a half-mile from Cataract Lake, quick and easy access to boating, fishing, kayaking, etc. awaits! Numerous nearby attractions are sure to provide great experiences (Cataract Falls, Exotic Feline Rescue Center, Terre Haute Casino, state parks, brewery/winery, local shops/eateries, etc.) And of course, simply enjoying time in and around the cabin itself is a fulfilling getaway!

Maria’s Haven
Welcome to “Maria’s Haven”💕 A beautiful cozy home in the heart of a beautiful small town. This home belonged to my mother, Maria, who passed away in 2020 to breast cancer. This home was truly her “Haven”. Take a walk to the local diner, museum, Gosport playground, local shops, or to our delicious Amish bakery. We are also just a few miles from the popular “Hilltop” restaurant as well as McCormicks Creek State Park. Our mission is to make you feel like you never even left home. ☺️

Grandpa's Cabin at Heidenreich Hollow
Grandpa’s Cabin at Heidenreich Hollow offers exclusive lodging on our hilly 5 acre wooded property. We offer a peaceful getaway from life while being right in the middle of both Indianapolis and Bloomington! Our quiet rustic cabin has a loft bedroom with stair access that includes a King size bed, 2 twin beds and an air mattress. We have a spacious bathroom and a fully equipped kitchen to help you feel at home. Search YouTube for Grandpas Cabin at Heidenreich Hollow for a video!.

The Main Street Retreat-NO CLEANING FEES
Enjoy your time to simply get away or as a must need sleep over due to travel or work. Only 14 miles south of I70. A Dollar General Store, Subway and Gas Station are nearby. Ten minute drive south to Sullivan for Walmart, restaurants, and grocery stores. Fifteen minute drive north to Terre Haute for all the city attractions. County and State Parks are near by as well. Located in a great neighborhood on main street with privacy. Maximum of only four adults allowed per reservation.

Enjoy Comfort & History! - Suite w/ Private Entry
We look forward to welcoming you to a private suite that is the guest quarters in our home. You’ll have a private entrance & 3 rooms to yourself. There’s a living room with a table and chairs, a bedroom with a queen-size bed - nightstands, dresser and closet space with hangers for your use - and a newly remodeled full bathroom. There’s also a kitchenette in the hallway which is an antique Hoosier Cabinet equipped with a microwave, mini-fridge, coffee pot, and hot water pot.

Cascade Cabin
Welcome to Cascade Cabin, our home away from home and yours! The charming log cabin is where a cozy rich wood aesthetic meets modern comforts. The beautiful remote cabin sits on 4 acres and is surrounded by mature trees and two glistening ponds. Enjoy your day exploring the nearby Cataract Falls and spend your evening around a bonfire. Enjoy the beautiful nature escapes that southern Indiana has to offer. We hope that you can enjoy this stunning getaway as much as we do!

Captain Bill's Guest House/seasonal swimming pool
Welcome to Captain Bill's Guest Lodge at Cagels Mill Lake! This gorgeous home offers modern amenities in a countryside setting. Perfect for bikers, boaters, fisherman, and anyone looking to enjoy lake life. Our guests are welcome to join us poolside at the main house. Our private pool is open only to us and our listed guests at our two Airbnb units. We're located seconds from the boat ramp and a short drive to Cataract Falls and Lieber State Park. Pool is seasonal.

Parke County Dream Cabin
Come experience the serenity of country living and get away from the daily grind of everyday life. Come fish in our five-acre lake (catch & release only), paddle-boat, kayak, or stroll through the woods. A covered porch and seating lakeside for relaxing. Located close to Mansfield and Bridgeton, 30 minutes from Turkey Run State Park, and only 30 minutes toTerre Haute or Greencastle. Come explore everything Parke County has to offer! KIDS WELCOME!
Popular amenities for Jennings holiday rentals
Other great holiday rentals in Jennings

Light-filled, Musician-friendly B-town Suite

Semi Off Grid Glamp Cabin

Historic Irvington 1st Flr Bedroom

Awesome Luxurious Downtown Indy Carriage Home!

Comfortable studio in prime location

The Dill Inn

Wood’s Edge Retreat

Canal-Side Comfort • Free Parking Downtown
Destinations to explore
- Chicago Holiday rentals
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- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Southern Indiana Holiday rentals
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- Columbus Holiday rentals
- St. Louis Holiday rentals
- Louisville Holiday rentals
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- Milwaukee Holiday rentals
- Lucas Oil Stadium
- Indiana Convention Center
- Eagle Creek Park
- Indianapolis Zoo
- Indianapolis Motor Speedway
- The Golf Club at Eagle Pointe
- Brown County State Park
- Indianapolis Canal Walk
- Brickyard Crossing
- Oliver Winery
- Butler University
- IUPUI Campus Center
- Gainbridge Fieldhouse
- Indianapolis Museum of Art
- Monroe Lake
- Childrens Museum
- Indiana State Museum
- McCormick's Creek State Park
- University of Indianapolis
- Speedway Indoor Karting
- Victory Field
- Circle Centre Mall Shopping Center
- White River State Park
- Soldiers and Sailors Monument




