Vacation rentals in Jennings

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Top-rated vacation rentals in Jennings

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

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Top guest favorite
Cabin in Unionville
5 out of 5 average rating, 208 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 favorite
The exterior of a single-story house is surrounded by freshly mulched landscaping and trees. A wooden deck leads to the front entrance, and a gravel driveway is visible. Sunlight filters through the branches, creating a serene outdoor atmosphere.
Home in Spencer
5 out of 5 average rating, 32 reviews

Artesian spring house Sleeps 4 Fire pit by creek

Completely renovated 1950s cottage! This home features 2 Bedrooms ,1 queen and one queen coil spring futon and full 2 baths. Guests can unwind with all of the amenities of home! Fire pit by the creek, bbg on the deck! Just minutes from Downtown Spencer, with several local destinations , Main Street Coffee, Civilian Brewery, and hiking at McCormicks Creek state park or Greens bluff nature preserve ! Finish it off at Owen Valley winery, with desert ! We look forward to hosting you at or home!

Guest favorite
A charming cabin exterior is framed by lush green trees, featuring a welcoming front porch with wooden railings and potted plants. The entryway is accentuated by a round window and vibrant red door, providing a cozy entry point to the retreat.
Guesthouse in Martinsville
4.97 out of 5 average rating, 76 reviews

Get away in the woods ! Fire pit, Game room

You will love this cozy private retreat a short drive away from bigger town amenities. Heading into Martinsville for some lunch (or candy!), checking out the beautiful landscape for some walking/hiking at Morgan-Monroe State Forest. Hunters Honey Farm 4.3 mi. Cedar Creek Winery, Brewery, Distillery 20 mi. Morgan Monroe State Forest 20 mi. Martinsville Candy Kitchen 15 mi. Art Sanctuary of Indiana 15 mi. TraderBakers Flea Market 15mi. sit by the fire pit and roast marshmallows, game room !!

Guest favorite
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 favorite
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 favorite
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, 167 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 favorite
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, 106 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.

Guest favorite
Cabin in Poland
4.97 out of 5 average rating, 30 reviews

Cozy Lofted Cabin (#1) 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 favorite
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, 112 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 sweet-smelling poplar walls, the cabin offers a full bed by a picture window, small TV, writer's desk/library, AC, 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.

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
4.79 out of 5 average rating, 24 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!

Top guest favorite
A single-story home is displayed, featuring a light-colored exterior with a red metal roof. A spacious porch, equipped with seating, is visible at the front. Surrounding grass is neatly maintained, and trees provide natural shade nearby.
Home in Brazil
4.93 out of 5 average rating, 384 reviews

Swans Nest

If you are looking for a place to get away from the stresses of life this is it. You can fish on our 10 acres lake, walk thru the woods or just relax on the porch swing. Only 5 minutes from the nearest town, 30 minutes from Terre Haute and 40 minutes from Indy. Front porch faces a walnut tree grove and back porch faces 10 acre lake. At least 3 State Parks are within 20 miles of this property. Also super close to the Parke County Covered Bridge Festival.

Top guest favorite
The exterior of the cabin showcases a rustic log structure with a green metal roof, surrounded by lush greenery. Two wooden rocking chairs with colorful cushions are positioned on the porch, inviting relaxation. Large windows provide a glimpse of the peaceful woodland setting.
Cabin in Nashville
4.96 out of 5 average rating, 123 reviews

Red Cedar Log Cabin | Romantic + Hot Tub

Cozy, secluded, and full of charm, Red Cedar Log Cabin is the perfect Brown County getaway for couples. Soak in the private hot tub, unwind by the wood-burning fireplace, and enjoy the peaceful wooded setting. With rustic character, modern comforts, and easy access to Nashville, trails, shops, and local dining, this cabin is made for quiet mornings, cozy nights, and unforgettable weekend escapes. Book your stay and experience Brown County at its coziest.

Popular amenities for Jennings vacation rentals

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  2. United States
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  4. Owen County
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