Holiday houses in Jennings

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Top-rated holiday rentals in Jennings

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Guest favourite
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 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, 147 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.

Top Guest favourite
Cabin in Poland
5 out of 5 average rating, 64 reviews

Cozy Lofted Cabin (#2) at Cataract Lake Getaway

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, 152 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
Apartment in Mooresville
4.82 out of 5 average rating, 217 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.

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, 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 favourite
Apartment in Indianapolis
4.98 out of 5 average rating, 421 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
A historic brick mansion is set on a green lawn, showcasing multiple arched windows and a distinct tower. The building's ornate details and broad steps leading to a central entrance are visible under a dramatic cloudy sky.
Guesthouse in Spencer
4.96 out of 5 average rating, 94 reviews

Summer Kitchen at The Hill

Come enjoy this spacious studio that has been remodeled from an old summer kitchen. Located on 6 acres in the town of Spencer, this is the perfect place to unwind and getaway, or use it as a jumping point to adventure at nearby McCormick's Creek or Cataract Falls. Walking distance to neighborhood grocery store, coffee shop, and restaurants. Within 30 minutes of Bloomington and Indiana University! The hosts live full time in the main house with 2 great danes.

Top Guest favourite
Home in Brazil
4.93 out of 5 average rating, 363 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 favourite
Guesthouse in Bloomington
4.96 out of 5 average rating, 407 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.

Top Guest favourite
A cozy outdoor seating area features a red umbrella providing shade over white chairs arranged on a patterned rug. A gravel path leads to the small camper, surrounded by lush greenery and colorful flowers that add a natural touch to the serene setting.
Campervan/RV in poland
5 out of 5 average rating, 46 reviews

Camper in Wooded Floral Setting. Grill, Firepit

Save with NO added cleaning fees!! Coleman Lantern LT 24 ' Camper set up with everything you need for a cozy getaway. Situated at the edge of the woods along the flower gardens and fire-pit seating area. ONLY ONE BED ONLY TWO GUESTS I don't know why Airbnb continues to list two beds when there are not my apologies for that there is only one bed and no fold outs of any kind nor is there room for a fold out or an extra person

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, 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.

Popular amenities for Jennings holiday rentals

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