Holiday houses in Osceola

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Top-rated holiday rentals in Osceola

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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, 276 reviews

Lux, Couples Hideout, Creek, Private Hot Tub,

*Imagine soaking in your private hot tub under the stars while a gentle creek flows just steps away. You are surrounded by trees and natural beauty. *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

Guest favourite
The exterior of a two-story home is viewed at dusk, surrounded by landscaped greenery and large trees. Smooth concrete leads to a spacious driveway with a garage. Soft light glows from the windows, enhancing the welcoming appearance of the property against a vibrant, colorful sky.
Home in Elkhart
4.88 out of 5 average rating, 138 reviews

Lakeshore Cottage🎣 🚣‍♂️Waterfront/Great Wi-fi

Book your next getaway at this charming lakefront home on Heaton Lake! Enjoy a 96" TV, swimming, fishing, 4 person paddle boat & kayaks. Large backyard is perfect for games, Corn hole boards are provided. Just 7 minutes from dining and shopping in Elkhart, easy toll road access & only 30 minutes to Notre Dame Stadium. 1 Gbps Fiber internet. Located in a quiet neighborhood with no parties, events, or fireworks allowed. No-noise policy after 9 PM. 6 driveway parking spaces; no street parking.

Top Guest favourite
The log cabin, surrounded by snow-covered ground, features a wooden facade with a stone base. A porch with railings and steps leads to large glass doors, allowing views of the wooded area in the backdrop. A fence runs in front, adding to the secluded atmosphere.
Cabin in Goshen
4.95 out of 5 average rating, 324 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 studio apartment is displayed, featuring a spacious bed with neutral bedding. A kitchen area comprises a countertop with two barstools and modern appliances. Natural light enters through two windows, while artwork adorns the walls. A soft glow from a lamp enhances the ambiance.
Guest suite in Elkhart
4.98 out of 5 average rating, 187 reviews

The Serenity Suite

The Serenity Suite is one of two listings to accommodate guests. This suite is a 230 sq ft. tiny house studio apartment created in 2022. A kitchen island with 2 barstools is in the center of the space. This can be used as a sit down eating spot or a dedicated workspace. The 3/4 bath boasts up to date accessories and soft, thirsty towels. Please check out our Whispering Pines listing for a more spacious area. It will accommodate 1-5 guests at a very competitive price.

Top Guest favourite
Home in Elkhart
4.98 out of 5 average rating, 122 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 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, 203 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!!!

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
4.96 out of 5 average rating, 269 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, 630 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, 417 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, 129 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!

Top Guest favourite
A modern house is nestled among lush greenery, featuring an inviting entrance with a gravel path. The structure showcases multiple levels with a mix of windows and balconies. Bright umbrellas are placed on the deck, providing shade to outdoor seating areas.
Apartment in Granger
4.95 out of 5 average rating, 856 reviews

Wayback House

Country setting. Apartment above our garage. Attached to our house. No Smoking. No Pets. No Parties. No shared space but with the shared wall, you will here sounds from our space including garage door, voices, kitchen noise, dogs may bark, etc. we try to keep noise levels down but we live here and you may hear us. WiFi in this location is sometimes spotty.

Top Guest favourite
A two-story home is nestled among trees, featuring a large deck with multiple seating areas. Expansive windows offer views of the surrounding greenery. The structure blends with the natural landscape, providing a sense of seclusion and tranquility.
Home in White Pigeon
4.97 out of 5 average rating, 110 reviews

Secluded forest retreat with view

38 acres of woods, hills, pond, creek 1 mile of hiking trails beautiful views from the home and hiking you will see many deer quiet and secluded no close neighbors whole home to yourself entire property to yourself fire ring with firewood at picnic area Gazebo wood burning stove and fireplace with firewood fast and dependable fiber optic wifi

Popular amenities for Osceola holiday rentals

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