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Vacation rentals in Jennings

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Top-rated vacation rentals in Jennings

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Guest favorite
The exterior of Namaste Lofts is shown, highlighting the red brick façade and large windows with green awnings. Nearby sidewalk seating is visible, along with surrounding storefronts, creating a vibrant downtown atmosphere.
Loft in Greencastle
4.97 out of 5 average rating, 204 reviews

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.

Top guest favorite
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, 148 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 favorite
A serene view of two small lakes is framed by tall trees and gentle slopes. Sunlight reflects off the water's surface, highlighting the tranquil setting. A rustic wooden fence borders the foreground, complementing the natural landscape.
Cabin in Monrovia
4.95 out of 5 average rating, 108 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

Guest favorite
A charming guest suite set against a backdrop of lush green trees. The single-story structure features a covered porch, large front windows, and a welcoming entryway, immersed in the tranquility of the natural surroundings.
Guest suite in Bloomington
4.96 out of 5 average rating, 209 reviews

Hideaway Hollow - A Woodsy Getaway

Hideaway Hollow is a cozy, private guest suite in Bloomington, Indiana. Located on the north side, it is just fifteen minutes from the heart of downtown Bloomington, IU stadium, and an hour from Indianapolis. Nestled in the forest, the suite offers a covered porch with a private entrance, a spacious living room, a kitchenette, and a master bedroom with a full bath. Suitable for up to four guests, come to enjoy the serenity of country living, the comforts of home, and easy access to the city.

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
4.97 out of 5 average rating, 153 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 favorite
Apartment in Mooresville
4.83 out of 5 average rating, 218 reviews

Apartment near Indianapolis airport

This is one of 4 apartments in large house sitting on 2 acres in the small town of Mooresville. We are conveniently located 7.1 miles from Indianapolis International Airport 18 miles from downtown Indianapolis 17 miles from Indianapolis Convention Center 35 miles from Indiana University in Bloomington. This apartment is upstairs. This house is not suitable for children under 12. If interested in booking, please answer our pre-booking questions found at the beginning of House Rules.

Guest favorite
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, 115 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 favorite
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, 110 reviews

Bridge-View Suite at Cataract Falls

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 favorite
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, 1,352 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 favorite
Guesthouse in Bloomington
4.96 out of 5 average rating, 409 reviews

Private Studio, 5 Min IU, Kitchen, Private Parking

Intentionally designed to feel comfortable, calm, and easy to settle in. At ~400 sq ft with a slanted ceiling, it's ideal for solo travelers or couples. Guests describe the studio as cozy, spotless, and surprisingly well-equipped — with everything needed for a comfortable stay. Minutes from IU, downtown, dining, parks, and Kroger, you’re close to everything without the hassle. Please inquire about discounted rates for extended bookings.

Superhost
An open-concept living space features a dining area with a wooden table surrounded by black chairs, seamlessly connected to a modern kitchen equipped with stainless steel appliances. Natural light pours in through a large window, highlighting the minimalist decor and inviting atmosphere.
Home in Indianapolis
4.85 out of 5 average rating, 133 reviews

Carriage Home w/ early check in

Discover the perfect blend of historical charm and modern convenience in our cozy home, located in the heart of Indianapolis' Old North Side. Offering early check-in, you can kick-start your exploration of the city without a moment's delay. Our prime location ensures you're just moments away from downtown's bustling scene, the Indiana Convention Center, Gainbridge Fieldhouse, and Lucas Oil Stadium. Free Parking Free Coffee

Top guest favorite
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, 143 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.

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