Holiday rentals in Medaryville

Technicolor River Retreat just outside of Chicago!

Escape the city hustle for a chic retreat on the serene Kankakee River. Our vibrant vacation home, just a stone's throw from Chicago & the Dunes, is a haven for groups & families. Revel in the quirky selfie walls, unwind by the fire pit, or fish off the private dock. Every corner is a conversation starter, from the colorful murals to the luxurious balcony. With high-end amenities and space for six, it's the perfect spot for a lovely reset. Book this incredible home for an unforgettable getaway!

Cozy barn loft on organic vegetable farm

Find peace and restoration in this beautiful barn loft at Perkins' Good Earth Farm. The loft has a bedroom, separate shower and toilet spaces, work area, sitting room, kitchen space, and heating/cooling fresh air system. Located above our farm store, the loft provides privacy for you while giving you access to fresh fruits & veggies, locally sourced meats, homemade soups & salads from our farm kitchen, and so much more. You can also walk our farm trails, visit the veggies, or enjoy a campfire.

The Lakeside Cove 4 bed 3 bath near Indiana Beach

Welcome to your ultimate Lake Shafer getaway -a beautifully updated retreat tucked away in Monticello, IN. ✔️Steps away from the entrance of Indiana Beach and the sparkling waters of Lake Shafer. ✔️4 Bedrooms & 3 Full Bathrooms ✔️Lakeside ✔️Cozy outdoor firepit & ample seating ✔️Game/Entertainment room with Arcade and Ping Pong ✔️Recent Updates PERFECT for: ✔️Family Vacations ✔️Indiana Beach weekends ✔️ Lake trips & boating weekends ✔️Relaxing fireside nights by the water ✔️Group getaways

Sunset Heaven Retreat 5 min from Bass Lake

Escape to tranquility with your loved ones at this serene retreat. This beautiful 2-acre estate offers a perfect blend of seclusion and convenience. Just a 5-minute drive from the beautiful shores of Bass Lake, where a public beach awaits, and a short 10-minute journey to the charming town Culver and Lake Maxinkuckee. Bring your boat or just rest by the lake. If power goes out we have a generator. Please note that all buildings, aside from the main house, are inaccessible to guests

Brightstone Lake Cabin 3

Discover this charming 2 bedroom cabin nestled by our 18-acre private lake. This fully furnished retreat offers a quite escape, complete with a well-equipped kitchen, laundry, and full bathroom. Explore a 1.5-mile lakefront walking trail, perfect for strolls and birdwatching. Enjoy a sandy swimming beach and excellent fishing opportunities right at your doorstep. Our cabin is ideal for both peaceful getaways and outdoor adventures, providing the perfect setting to unwind and explore.

Lakeside Haven: 4 bed/2 bath/sleep 11 on the water

Lakeside Haven: Your Dream Walk-Out Ranch Getaway in Monticello, Indiana Welcome to your serene escape on the shores of Lake Shafer—where peaceful mornings, adventure-filled afternoons, and golden hour sunsets create the perfect backdrop for memories that last a lifetime. Tucked away on a private, wooded lot in beautiful Monticello, Indiana, this stunning 4-bedroom, 2-bathroom walk-out ranch is your invitation to unwind, recharge, and reconnect with the ones who matter most.

The Loft at Virgie

You don't have to be born in a barn to vacation in one. Trade in the city for millions of stars in the night sky! As you enter thru the French doors you will be greeted by an open concept room decorated with a barn/industrial motif. Knotty pine car-siding and galvanized steel, wood floors along with a reclining leather couch and love seat fill the room A full kitchen with granite counter tops await you. There is plenty of natural lighting for the evenings.

Quiet & Serene Waterfront Condo Fit for a King

This unique place has a style all its own. Unwind around a campfire by the water & wake up to nature at this charming 2-bedroom, 1-bath vacation rental in Buffalo, near Monticello. Perfect for a peaceful retreat, this condo offers convenient access to local restaurants and attractions. Spend your days fishing, exploring the Indiana Beach Boardwalk, or simply soaking in the serene ambiance from either deck each evening. Your ideal getaway awaits—reserve today!

Home of 1888

Conveniently located 6 1/2 miles from I-65 between the Lowell and Roselawn exits and 6 miles from Sandy Pines Golf course & The Pavilion. This fully updated place has everything to feel right at home. The kitchen is provided with everything you need to prepare a meal. Plenty of places to eat out are just down the street. A 43" Samsung smart TV with Sling TV and Paramount Plus. When it's time to rest you'll do so on a brand new Nectar memory foam beds.

Cozy Lakefront home on beautiful Bass Lake, IN

Welcome to The Lakehouse & Cabana on beautiful Bass Lake, IN. Step in to our cozy home for a relaxing stay, taking in all the views of calming waters and nature on display. A weekend getaway, or maybe a little longer stay, this location offers the perfect escape for rejuvenation. Enjoy a bonfire to warm up an evening gathering, while sipping on some hot cocoa. If fishing is on your list of favorite activities, our cove allows for a great catch!

Rustic Lodge -Oak Tree Lodge

The Oak Tree Lodge is located in a country setting and offers a private lodge with an outdoor area for relaxing and entertaining. The former barn structure has been beautifully transformed in a rustic and comfortable lodge to rest, relax, and renew. We have renewed it into a fresh new life - as a lodge to invite friends and guests to enjoy and relax. The listed rate is for four people, and additional quests will be $25.00 per person.

Artu

Enjoy the view of the Tippecanoe River when you stay at Artu! The backyard has access directly to the river, where you can sit around the firepit and watch the water go by as you relax with your family and friends. This house is located just down the road from the town park and walking distance to the riverside rentals. Please be aware you are not in a big city, some resources will be limited.