Holiday rentals in Jennings

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Top-rated holiday rentals in Jennings

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

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Top guest favourite
Cabin in Unionville
5 out of 5 average rating, 210 reviews

Elevated Wilderness | Mindful Retreat | 2 Kings

Executive Forest Sanctuary/2 King Beds, Hot Tub & Trails Escape to an architectural masterpiece set on 40 private, wooded acres. Designed for professionals, couples, and active adults seeking a high-end nature reset, Cabin Porch Paradise balances complete seclusion with proximity to Southern Indiana’s best destinations. Whether you are unwinding in the spa amenities, working remotely via high-speed fiber, or exploring the surrounding lakes and state parks, this is your ultimate ridgetop retreat.

Top guest favourite
A charming one-room cabin features a wooden exterior with a green metal roof. Two blue chairs are placed on the small porch beside a door, which invites guests to enjoy the surrounding greenery in a tranquil setting.
Cabin in Bainbridge
4.94 out of 5 average rating, 115 reviews

Covered Bridge Cabin (on Big Walnut Creek)

Retreat and renew in this charming one-room cabin right by Big Walnut Creek and Baker's Camp Covered Bridge. Fish, kayak, or swim; hike or birdwatch in a nearby preserve; read, write, find inspiration. With its raw poplar walls, the cabin offers a full-sized bed by a picture window, small TV, writer's desk/library, air conditioning, fans, baseboard heat, kitchenette, toilet, sink, outdoor shower (before first frost), small porch, grill, and a fire pit. (No wifi in cabin!) Simple and beautiful.

Guest favourite
A rustic log cabin with a red metal roof is nestled among tall trees, showcasing a blend of original character and modern updates. Surrounding the cabin is natural terrain, with a spacious deck featuring outdoor seating against a backdrop of greenery.
Cabin in Poland
4.89 out of 5 average rating, 38 reviews

Pioneer Log Cabin on the Lake

Take a step back in time to a simpler way of life! Enjoy this log cabin that was originally built in the pioneer days. While the cabin retains the charm of the 1800's, it also has been updated with basic amenities like electricity, indoor plumbing, hot water, and everything you would expect from a modern cabin. Located on Cataract Lake, yards from a public boat launch, this is the perfect spot to get out onto the lake or just relax amongst the trees. Boat parking is provided on the property.

Top guest favourite
Home in Cloverdale
4.94 out of 5 average rating, 35 reviews

Overnight on Main

Overnight on Main is the perfect stay if you are visiting the west side of Indiana. Here's what you'll have easy access to! - Indianapolis International Airport - 28 minutes east - Cataract Falls State Rec/ Park - 11 minutes south - DePaw University/ Greencastle - 15 minutes north - Lieber State Rec/ Park - 10 minutes southeast - C Bar C Expo Center - 2 miles north (4 min) You will also have easy access to local amenities and restaurants, some just a quick walk across or up the sidewalk!

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
4.98 out of 5 average rating, 168 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. ☺️

Top guest favourite
A panoramic view of the dome's interior highlights the unique wooden ceiling design, featuring triangular shapes. A dining table with blue placemats accommodates six, surrounded by large windows and stained glass accents, allowing natural light to fill the space.
Home in Bloomington
4.96 out of 5 average rating, 107 reviews

There's No Place Like Dome!

Come enjoy fabulous Bloomington, IN from your own private paradise! The 1400 square-foot renovated dome home boasts panoramic wooded views and sits on 6 acres of a secluded, park-like setting only 17 min. from downtown. The dome sleeps 4 guests with an open, divided, (not fully private) loft with one full bed and one queen bed. There is one full bath, dining for six, island seating and a fully equipped kitchen. It also features a fireplace, laundry facilities and front and back decks.

Top guest favourite
Cabin in Poland
4.98 out of 5 average rating, 44 reviews

Cozy Lofted Cabin (#3) at Cataract Lake Getaway

This 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, C Bar C Event Center, Exotic Feline Rescue Center, 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
The entrance to the cabin features a covered porch with rustic wooden supports and decorative string lights. A welcoming outdoor seating area is visible in the background, surrounded by lush greenery and shaded by nearby trees. The path is lined with stones and small plants.
Cabin in Unionville
5 out of 5 average rating, 505 reviews

Cozy Cabin Close to University 1

The Red Rabbit Inn is located just 15 mins from the Indiana University campus and just 20 mins from Nashville, IN , this architecturally designed cabin features the works of local artisans. Beautifully landscaped on a secluded, wooded pond, this cabin includes a loft bedroom with KING bed, bath, full kitchen, gas fireplace, TV & Wifi, with your own private deck, outdoor hot tub, fire pit area & gas grill. Cabin sleeps 2 guests. Located near Lake Lemon, in a beautiful serene setting.

Superhost
A log cabin exterior is shown, featuring a dark brown wood facade and a welcoming yellow door. The cabin has a second-floor balcony and a stack of firewood nearby. Snow lightly covers the ground, and tall pine trees are visible in the background.
Cabin in Spencer
4.8 out of 5 average rating, 25 reviews

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!

Superhost
Tiny home in Poland
4.86 out of 5 average rating, 7 reviews

Woodlands at Countryside Estates

Escape to nature in this charming tiny glamping cabin nestled near Cagles Mill Lake. This peaceful retreat sits near the end of a private lane in Countyside Estates, surrounded by a rustic woodland setting, perfect for those seeking solitude, camping with modern conveniences or a quiet getaway. It’s located near the public boat launch for Cagles Mill Lake to enjoy many water sport activities. (1.9 miles) The cabin is also close to Lieber State Rec Area and Cataract Falls.

Guest favourite
A modern home is positioned on a hillside, featuring a sleek black exterior and large windows that allow for ample natural light. A balcony extends from the structure, providing outdoor seating and a view of the surrounding trees.
Cabin in Nashville
5 out of 5 average rating, 523 reviews

Modern Nashville Home in the Woods

Welcome to Plāhaus — a modern retreat tucked into the woods of Brown County. #1 Most-wishlisted Airbnb in Indiana per Airbnb Designed for solitude, relaxation, and connection with nature, Plāhaus blends modern architecture with peaceful surroundings. Take in the views from the balcony, gather around the firepit, or explore nearby Nashville’s shops and restaurants. Perfect for romantic getaways, family escapes, or simply recharging from everyday life.

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, 298 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!

Popular amenities for Jennings holiday rentals

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