Holiday rentals in Jennings

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Top-rated holiday rentals in Jennings

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Top guest favourite
A sprawling green field stretches towards the horizon, filled with soft clover and dotted with trees. In the foreground, a planter holds bright flowers, adding colorful contrast to the natural landscape. The sky is lightly clouded, enhancing the serene atmosphere.
Guest suite in Bloomington
4.99 out of 5 average rating, 144 reviews

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.

Guest favourite
A wooden dock extends over the calm surface of the lake, surrounded by trees displaying autumn colors. The path leading to the dock is lined with sturdy posts, inviting exploration of the serene lakeside setting.
Cabin in Monrovia
4.95 out of 5 average rating, 107 reviews

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

Top guest favourite
Cabin in Poland
5 out of 5 average rating, 62 reviews

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!

Top guest favourite
An exterior view of the home is captured, featuring a light gray facade and metal roof. Colorful flowers and pumpkins decorate the landscaped garden, complemented by a bench positioned under a tree. Neatly arranged windows provide an inviting look to the property.
Home in Gosport
4.97 out of 5 average rating, 149 reviews

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. ☺️

Guest favourite
The living area features wooden walls and ceilings, complemented by large windows that allow natural light to illuminate the space. Two seating areas include a brown sofa adorned with cushions and a rust-colored recliner, alongside a coffee table. A dining area can be seen in the background.
Cabin in Martinsville
4.91 out of 5 average rating, 501 reviews

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!.

Top guest favourite
A view of the dining area is presented, featuring a wooden table set in the center beneath a pendant light. The floor is adorned with a patterned rug, surrounded by windows that allow for natural light. A sideboard can be seen against the wall.
Home in Farmersburg
4.9 out of 5 average rating, 114 reviews

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.

Top guest favourite
A spacious great room is featured, equipped with a comfortable black sofa and a wooden coffee table. A kitchenette is visible with modern appliances, and a curved bar area with stools provides additional seating. Recessed lighting and a ceiling fan illuminate the area.
Villa in Spencer
4.94 out of 5 average rating, 109 reviews

Bridge-View at Cataract Falls Lodge

Welcome to Cataract Falls Lodge at the entrance to the Cataract Falls State Recreation Area. A one minute walk from the lodge and you will be standing on the overlook of the most spectacular waterfall in the Midwest. The lodge has three private suits that can be rented individually or combination thereof. This unit, Bridge-View, sleeps 4 offering one bedroom, a great room with attached kitchenette, full bathroom and personal outdoor space overlooking the entrance to the park.

Top guest favourite
Flat in Indianapolis
4.98 out of 5 average rating, 418 reviews

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.

Top guest favourite
The entrance features a cozy porch with a small table and chairs surrounded by greenery. A decorative broom is suspended from the porch’s overhang, and a stone pathway leads to the front door, accented by the house number displayed on a stone pillar.
Guest suite in Bloomington
4.95 out of 5 average rating, 1,342 reviews

Strawbale Bungalow. Bloomington Indiana USA.

Art and book filled. Located in Bloomington Indiana. My 1920s bungalow includes two guest bedrooms with queen sized beds, down comforters, feather/down pillows, line curtains and private bathroom. The guest area also includes a garden porch, private entrance, living room and, dining area with microwave, small refrigerator and handmade maple table. NO KITCHEN. The bathroom is between the bedrooms and includes a Toto washlet bidet and EO toiletries.

Top guest favourite
A single-story cabin is framed by lush greenery, showcasing natural wood siding and a welcoming front porch. The porch features seating arrangements and decorative elements, while the pathway leads to a gravel driveway, enhancing the serene ambiance of the surrounding woods.
Cabin in Carbon
4.98 out of 5 average rating, 253 reviews

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!

Top guest favourite
A cozy living area features a dark gray sofa adorned with yellow and patterned throw pillows. A television is mounted on the wall, with a wooden entertainment center below. A lamp stands beside the couch, and a potted plant is positioned near a window.
Loft in Spencer
5 out of 5 average rating, 142 reviews

Carriage House 1 bedroom loft suite w/ fireplace.

Keep it simple at this peaceful and centrally-located loft. Carriage House Guest Suite is located in a quiet neighborhood just five blocks from the courthouse square. Spencer's historic downtown offers the restored Tivoli theater, restaurants, art galleries & shops. Two miles from beautiful McCormick's Creek State Park and 3 miles to Owen Valley Winery. A convenient 20 miles to downtown Bloomington & Indiana University.

Top guest favourite
The living area features a comfortable gray sofa and two armchairs, inviting relaxation. A round coffee table sits at the center, with a soft area rug underneath. The space is filled with natural light, complemented by warm lamps, while shelves in the background house decorative items.
Loft in Mooresville
5 out of 5 average rating, 397 reviews

Loft Apartment: Beautiful Farm and Country Views

This beautiful, over the garage private apartment is located in a wooded area across from our 94 acre farm. A very peaceful setting to wind down and enjoy the nature around you. Conveniently located 15 minutes from the airport and 30 minutes from downtown Indianapolis. A work space is also available that overlooks this beautiful farm!! Also perfect for couples or small families to enjoy some time in the country!

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