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Vacation rentals in Osceola

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Top-rated vacation rentals in Osceola

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Top guest favourite
A welcoming entrance to the log home is framed by manicured grass and landscaped flower beds. The wooden porch offers a spacious area for relaxation, while the surrounding trees provide a natural, serene backdrop. Colorful flowers dot the garden, enhancing the outdoor appeal.
Guest suite in Cassopolis
4.99 out of 5 average rating, 391 reviews

The Hideaway on Mitchellii Lane

A completely furnished apartment in the basement of our log home (our main residence) on 5 acres of woods above beautiful Shavehead Lake. Entrance into the apartment through a screened in porch and double French doors provides privacy and space to relax and enjoy the beautiful outdoor landscape. A large egress window allows natural sunlight into the bedroom on the opposite side of the wall from the kitchen/dining room/living room. High speed internet & YouTubeTV provide entertainment options.

Top guest favourite
The exterior of a circular, dark-hued building is illuminated by warm string lights during twilight. A private hot tub and a fire pit with chairs are visible, while the surrounding natural landscape emphasizes the peaceful setting.
Farm stay in Vandalia
5 out of 5 average rating, 263 reviews

Luxury Country Retreat for Romantic Escape, Creek

*Escape to your private couple’s retreat. *Whether sipping coffee at sunrise or star gazing, The Grain Binn is the perfect blend of rest and charm *Situated on 70 acres with flowing creek *Pickle Ball court 1 mile from Binn *Fully stocked kitchen *Fireplace *Hot tub with towels provided * Firepit with firewood *Bird feeder for Bird lovers *King size bed with quality bedding *Forgot something? Got cha *In floor heat *Snacks *Walking trails *Good WIFI *Unplug to reconnect

Top guest favourite
The cabin is constructed of warm wood, surrounded by lush greenery and tall pine trees. A welcoming front porch features two chairs and flower beds, inviting relaxation. Large glass doors provide views of the outdoor space, enhancing the connection with nature.
Cabin in Goshen
4.95 out of 5 average rating, 307 reviews

Tiny home log cabin at the pines

Nurture your most important relationships at this peaceful authentic log cabin, built in 2022, set halfway in the long lane of our 18 acre property. Enjoy privacy with the massive pine trees behind you. Relax on the front porch and watch the sunset beyond the horse pasture and cornfields. The cabin boasts Wi-Fi, TV screen w options,a soaker tub, queen bed, recliners with heating feature, a full kitchen stocked with pots and pans, a washer and dryer. Everything you need for a longer stay.

Top guest favourite
A serene riverside view captures vibrant autumn foliage reflected in calm waters. Comfortable seating is arranged on a stone patio, overlooking the river, enhancing the tranquil outdoor experience. Sunlight dances on the water's surface, inviting relaxation and connection with nature.
Apartment in Mishawaka
4.96 out of 5 average rating, 555 reviews

Private Entrance Guest Suite on the River

Stay in our studio apartment suite with private exterior door entrance. Hosts live in the rest of the house. From the backyard you can fish, kayak/canoe, paddle board, enjoy a bonfire, grill, and relax by the river. There's a king memory foam bed, sleeper sofa, and 49" TV. Remote work friendly with spacious workspace desk, fast WIFI, and coffee. The closet has a mini food prep area with mini fridge and microwave, and grill out on back patio. It's a quick 15 min drive to Notre Dame.

Top guest favourite
Home in Elkhart
4.99 out of 5 average rating, 116 reviews

Cozy family friendly oasis |4 BR |River views|ND

Relax and unwind with the whole family !Unpack and enjoy our quiet and safe neighborhood with beautiful views of the river for those evening walks! The 4 bedroom 2 bath comes with a fully stocked kitchen and lounging areas to watch your favorite shows and movies. Enjoy the views of the channel from the gas grill as you prepare a delicious meal with the family. After a good meal, make some memories with some board/card game Close to great restaurants and hospital near by.

Guest favourite
A spacious grassy area overlooks Buck Lake, framed by lush greenery and trees along the shoreline. The sky is filled with fluffy clouds, reflecting a serene atmosphere. A dock extends into the water at the far end, inviting relaxation and outdoor activities.
Home in Vandalia
4.92 out of 5 average rating, 113 reviews

Quiet cottage on Buck Lake, 1 bedroom

Take it easy at this unique and tranquil getaway at Hummingbird Hill Cottage!You’ll be on peaceful and beautiful, no-wake Buck lake where you can enjoy kayaking, paddleboarding, fishing, and more! Take a hike, ride bikes, or play disc golf in the beautiful Dr. Lawless International Dark Sky Park which is directly across the street! Whether you’re looking to have a couples getaway, a guys’ fishing trip or time with girlfriends, Hummingbird Hill is for you!

Top guest favourite
A modern kitchen area is highlighted by a large central island with a white countertop. Exposed brick walls add character, while vintage signage provides a nostalgic touch. A cozy seating arrangement features a small chair and a fireplace TV setup against the wall.
Guest suite in Middlebury
5 out of 5 average rating, 112 reviews

Mullet's Speed Shop

Refresh and relax at this newly constructed guest suite! Mullet's Speed Shop is conveniently located just 3 minutes from the famous Das Dutchman Essenhaus Restaurant and Bakery, less than 10 miles from the quaint shops of Shipshewana, and an easy 40 minute drive to Notre Dame (for the football fans). Take a bike ride or a peaceful walk on the Pumpkinvine Nature Trail less than 2 miles away. Nestled in the heart of Amish country, enjoy the buggies passing by!

Top guest favourite
A cozy living area features a dark sofa adorned with patterned cushions, complemented by two green accent chairs. A circular coffee table with a game sits at the center, and a flat-screen TV is mounted on the wall. Warm light emanates from two lamps, adding a welcoming touch.
Guest suite in Bremen
4.98 out of 5 average rating, 202 reviews

Blended Threads: Barn Stay -cozy & stylish, ND!!!

Looking to stay at a gorgeous & one of a kind space? This modern barn has a beautifully renovated, private apartment for you to enjoy located in the walkout basement of our home; It is close to downtown Wakarusa, Mishawaka, South Bend & only 25 minutes from the Irish of ND! Cozy up in front of the fireplace with coffee & a book, play some board games in the silo-lounge, or make this luxurious space home, while you get out and explore!!!

Top guest favourite
A bright living area showcases a combination of comfortable seating, including two armchairs and a sofa, arranged around a round coffee table. A dining table is positioned nearby, featuring a neutral tablecloth and a potted plant centerpiece. Light filters through sheer window curtains.
Bungalow in Elkhart
4.97 out of 5 average rating, 261 reviews

The Boho Bungalow

The Boho Bungalow is an updated 1920's bungalow with plenty of traditional charm. Wood floors, built ins and vintage kitchen make it cozy and welcoming. It's perfect for traveling professionals or families needing short term housing while visiting the Elkhart/South Bend area. The home is just blocks from Elkhart General Hospital and is very convenient to downtown Elkhart, Granger and South Bend. It's less than 15 miles from Notre Dame.

Top guest favourite
The image displays a creatively designed sign reading 'Silk on the Bend,' set against a textured, warm brown brick wall. The lettering features a combination of bold and cursive styles, enhancing the welcoming identity of the space.
Guest suite in Osceola
4.94 out of 5 average rating, 626 reviews

Silk On the Bend

My place is close to 80/90 Toll -road exit 83-Mishawaka IN. Visit us for events at :Notre Dame/St. Mary's/Bethel college/Holy Cross College. Mileage to ND Campus is 11.4. 15 Minutes to Elkhart Aquatic Center. Approx 20 Min to Four Winds Casino (Via the 20 Bi-pass) This Spring 2021 The Silk was chosen by AIRBNB as the 2d best place to stay in the greater South Bend-Mishawaka area. I close in January and February but re-open in March.

Top guest favourite
A charming log cabin features a welcoming facade with large windows framed by wooden accents. The entrance is accessed via a stone pathway lined with landscaped garden beds, showcasing lush greenery and colorful plants. Surrounding trees provide a serene, natural setting.
Cabin in Middlebury
4.99 out of 5 average rating, 400 reviews

Cabin off 39 - Peaceful, private one bedroom cabin

Kick back and relax in this calm, stylish space. Nestled among the trees, it provides a quiet getaway from the chaos of life allowing you to recharge and renew. The main residence is approximately 400 feet from the cabin. The cabin is secluded and yet close to local attractions, restaurants, biking and nature trails. The Cabin has a total of 420 sq ft living space with 280 sq ft on the ground floor and a 140 sq ft bedroom loft.

Top guest favourite
Home in Elkhart
4.99 out of 5 average rating, 117 reviews

Little House On The River

Escape to the Little House On The River in Elkhart, IN! This cozy 1-bedroom, 1-bath retreat sleeps 4 and offers stunning river views, a private deck, and all the comforts of home. Just 30 minutes from Notre Dame and a short drive to Shipshewana, it’s the perfect spot for game days, Amish country exploring, or simply relaxing by the water. Peaceful, private, and unforgettable—your riverside getaway awaits!

Popular amenities for Osceola vacation rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. St. Joseph County
  5. Osceola